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Hindawi Publishing CorporationJournal of ChemistryVolume 2013 Article ID 530135 9 pageshttpdxdoiorg1011552013530135

Research ArticleSynthesis Antimicrobial and Antioxidant Activities ofN-[(51015840-Substituted-21015840-phenyl-1H-indol-31015840-yl)methylene]-5H-dibenzo[bf]azepine-5-carbohydrazide Derivatives

Anand R Saundane1 Vijaykumar Tukaram Katkar1 and A Verma Vaijinath2

1 Department of Post-Graduate Studies and Research in Chemistry Gulbarga University Gulbarga Karnataka 585 106 India2 Shri Prabhu Arts Science amp J M Bohra Commerce College Shorapur Karnataka 585 224 India

Correspondence should be addressed to Anand R Saundane arsaundanerediffcom

Received 30 May 2013 Revised 26 August 2013 Accepted 28 August 2013

Academic Editor Hasim Kelebek

Copyright copy 2013 Anand R Saundane et al This is an open access article distributed under the Creative Commons AttributionLicense which permits unrestricted use distribution and reproduction in any medium provided the original work is properlycited

The main aim of the present study was to synthesize new leads with potential antimicrobial and antioxidant activities As a partof systematic investigation of synthesis and biological activity some new indole compounds 3andashc and 4andashc were prepared andscreened for their antimicrobial and antioxidant activities The antimicrobial evaluation of newly synthesized compounds wascarried out by cup-plate method Antimicrobial activity results revealed that compound 4a showed promising activity againstbacteria Staphylococcus aureus Klebsiella pneumonia and Pseudomonas aeruginosa and exhibited maximum inhibition againstAspergillus niger Aspergillus oryzae Aspergillus terreus and Aspergillus flavus The antioxidant activity was performed by threemethods namely radical scavenging activity (RSA) ferric ions (Fe+3) reducing antioxidant power (FRAP) and metal chelatingactivity by using Hatanorsquos Oyaizursquos and Dinisrsquo methods respectively Compound 4a showed promising RSA FRAP and metalchelating activity

1 Introduction

The emergence and spread of antimicrobial resistance havebecome one of the most serious public health concernsacross the world In last few years it was reported that indoleits bioisosteres and derivatives had antimicrobial activityagainst Gram-negative Gram-positive bacteria especiallyagainst Pseudomonas aeruginosa Escherichia coli and Staph-ylococcus epidermidis and the yeast Candida albicans [1]and so forth On the other hand indolyl compounds arevery efficient antioxidants protecting both lipids and pro-teins from peroxidation It is well known that the indolestructure influences the antioxidant efficacy in biologicalsystems [2] Indole derivatives have been reported to possessa variety of physiological and pharmacological activities likeantibacterial [3] antifungal [4 5] antioxidant [6] anticancer[7 8] analgesic [9] antiasthmatic [10] and antiviral [11]and to be effective in treatment of sexual dysfunction [12]An effective anticonvulsant drug 5H-dibenzo[bf]azepine-5-

carboxamide was first synthesized by Schindler [13] in 1960and since then it has become the most frequently pre-scribed first-line drug for the treatment of epilepsy In addi-tion dibenzo[bf]azepine derivatives are useful due to theirantimicrobial [14] antioxidant [15 16] and antitubercular[17] activities

Thiazolidinone a saturated form of thiazole with car-bonyl group on fourth carbon has been considered as amagic moiety (wonder nucleus) because it gives out novelderivatives with different types of biological activities Thisdiversity in the biological response profile has attractedthe attention of many researchers to explore the potentialbiological activity (such as antibacterial [18] antifungal [19]and antioxidant [20 21] activities) of this skeleton

We have reported earlier the synthesis antioxidant andantimicrobial activities of indole analogues containing thia-zolidinone derivatives such as 3-[4-(4-substituted)thiazol-2-yl]-2-(2-phenyl-1H-indol-3-yl)thiazolidin-4-ones (1) [22]

2 Journal of Chemistry

S

NN S

O

R

S

NN S

NH

O

R

N

N N

ON S

NHNH

O

NH

Ph

NSN

N

S

OO

1 2

3 4

R

H3C

H3C

CH3

Figure 1 Motivation for synthesis of antimicrobial and antioxidant active compounds

2-(5-substituted-2-phenyl-1H-indol-3-yl)-3-(5-(pyridin-4-yl)-134-oxadiazol-2-yl)thiazolidin-4-ones (2) [23] 2-(5-sub-stituted-2-phenyl-1H-indol-3-yl)-3-(4-phenylthiazol-2-yl)thi-azolidin-4-ones (3) [24] and 256-trimethyl-3-[2-(2-phenyl-5-substituted-1H-indol-3-yl)-4-oxothiazolidin-3-yl]thieno[23-d]pyrimidin-4(3H)-ones (4) [25] (Figure 1) Prompted bythese results we herein report the synthesis of title com-pounds and the evaluation of their antimicrobial and anti-oxidant activities

2 Result and Discussion

Thepathway for the synthesis of title compounds is illustratedin Scheme 1 Cyclocondensation of 5H-dibenzo[bf]azepine-5-carbohydrazide (1) [26] with 5-chloro-2-phenyl-1H-indol-3-carboxaldehyde (2a) [27] gave the intermediate N-[(51015840-chloro-21015840-phenyl-1H-indol-31015840-yl)methylene]-5H-dibenzo[bf]azepine-5-carbohydrazide (3a) Further compound (3a)on refluxing with thioglycolic acid afforded N-[2-(51015840-sub-stituted-21015840-phenyl-1H-indol-31015840-yl)-4-oxothiazolidin-3-yl]-5H-dibenzo[bf]azepine-5-carboxamide (4a) The structures ofall these previously unknown compounds were characterizedby spectral studies and elemental analysis

21 Antimicrobial Activities All the synthesized compounds(3 and 4) were evaluated for their antibacterial activityagainst Escherichia coli (MTCC-723) Staphylococcus aureus(ATCC-29513) Klebsiella pneumoniae (NCTC-13368) andPseudomonas aeruginosa (MTCC-1688) and antifungal activ-ity against Aspergillus niger (MTCC-281) Aspergillus oryzae(MTCC-3567T)Aspergillus terreus (MTCC-1782) andAsper-gillus flavus (MTCC-1973) by cup-plate method [28] Thezone of inhibition (in mm) was compared with the inhibi-tion zones obtained using streptomycin and fluconazole as

positive controls for antibacterial and antifungal activitiesrespectively The results are tabulated in Tables 1 and 2

Antibacterial screening revealed that compound 4a hav-ing chloro substitution at C-5 position of indole and diben-zo[bf]azepine ring along with thiazolidine system showedthemaximum inhibition against S aureusK pneumonia andP aeruginosa at all concentrations Compound 3a exhibitedmaximum inhibition against K pneumoniae due to the pres-ence of chloro substitution at C-5 position whereas com-pounds 3b and 4b showed maximum inhibition against Saureus and E coli respectively

Antifungal activity assay revealed that the compounds 3aand 4a exhibited maximum inhibition against A niger Aoryzae andA flavusThis enhanced activity of 3a and 4amaybe due to the presence of chloro substitution atC-5 position ofindole ring Also compound 4a showed good activity againstA terreus Compound 3b exhibited higher activity againstA niger A oryzae and A flavus at all concentrations Asdeduced from above stated results in general the presenceof the chloro or methyl substitution at C-5 position ofindole enhanced the activity of the compounds Differencesin standard deviation were calculated by means of ANOVAs(Tukey) using GraphPad instat software

22 Antioxidant Activities

221 11-Diphenyl-2-picryl Hydrazyl (DPPH) Radical Scaveng-ing Activity (RSA) Antioxidants are intimately involved inthe prevention of cellular damage cancer aging and a varietyof diseases DPPH is stable free radical that can accept anelectron or hydrogen atom and its stability originates fromdelocalization of the unpaired electron over the molecule

Free radicals are highly reactive species with one ormore unpaired electrons in their last orbital Reactive oxy-gen species (ROS) important in biological systems include

Journal of Chemistry 3

N

O

N

NH

NNH

O

N

NH

NNH

O

R

S

O

NH

CHO

1

3andashc4andashc

2andashc

Where a b cR = Cl CH3 H

NHNH2

HSCH2COOH

+

R

R

Scheme 1 Synthetic pathways for indole analogues (3 and 4)

superoxide (O2

∙minus) hydroxyl (∙OH) peroxide (ROO∙) alkoxy(RO∙) and hydroperoxy (HOO∙) radicals whereas majornonradical reactive species are hydrogen peroxide (H

2O2)

hypochlorous acid (HOCl) peroxynitrite (ONOO) nitricoxide (NO) and singlet oxygen (1O

2) Once formed ROS

are highly reactive radicals which can start a chain reactionTheir primary danger comes from the damage they can dowhen they react with important components such as DNARNA or the cell membrane [29] Investigation of the RSA ofthe test compounds was conducted as described by Hatanoand colleagues [30] and results were compared with theresults obtainedusing standards 2-tert-butyl-4-methoxy phe-nol (butylated hydroxyl anisole BHA) 2-(11-dimethylethyl)-1 4-benzenediol (tertiary butylated hydroquinone TBHQ)and ascorbic acid (AA) (Figure 2)

The RSA results revealed that the compound 4a showedhighest activity (7663) whereas the compounds 3a 3band 3c exhibited good RSA (7550 7011 and 6685) at100 120583gmL concentration Differences in standard deviationwere estimated by means of ANOVAs (Tukey) using Graph-Pad instat software and MS-Excel

222 Ferric Ions (Fe3+) Reducing Antioxidant Power (FRAP)Ferric ion (Fe3+) is relatively biologically inactive form ofiron However it can be reduced to the active Fe2+ dependingon the condition particularly pH [31] and oxidized backthrough Fenton-type reaction [32] with the production ofhydroxyl radical or Haber-Weiss reaction with the generationof superoxide anions Reducing power is to measure thereductive ability of an antioxidant and it is evaluated by thetransformation of Fe3+ to Fe2+ by donation of an electron inthe presence of test compoundsTherefore the concentrationof Fe2+ can bemonitored bymeasuring the formation of PerlrsquosPrussian blue at 700 nm (Figure 3)

Determination of the reducing power of the compoundswas conducted by a method described in [33] using BHA

0102030405060708090

100

25 50 75 100

Inhi

bitio

n (

)

Concentration (120583gmL)

3a3b3c4a4b

4cBHATBHQAA

Figure 2 DPPH RSA of the compounds (3-4)

TBHQ and AA as standards The FRAP results revealedthat compound 4a showed considerable high activity at theconcentrations of 50 75 and 100120583gmL whereas compound3b exhibited promising activity at the concentration of100 120583gmL Differences in standard deviation were calculatedby means of ANOVAs (Tukey) using GraphPad instat soft-ware and MS-Excel

223 Ferrous (Fe2+) Metal Ion Chelating Activity Metalchelating capacity reduces the concentration of the catalyzingtransition metal in lipid peroxidation It was reported thatchelating agents which form 120590-bonds with a metal areeffective as secondary antioxidants because they reduce theredox potential thereby stabilizing the oxidized form ofmetal ion [34] Fenton reaction accelerates peroxidation by


Table1In

vitro

antib

acteria

lactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Ecoli

Saureus

Kpn

eumoniae

Paeruginosa

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500

3a10plusmn1259plusmn1255plusmn0829plusmn1639plusmn0829plusmn08212plusmn12512plusmn32712plusmn0825plusmn0828plusmn12510plusmn082

3b9plusmn0826plusmn0821plusmn03714plusmn15514plusmn08314plusmn1275plusmn1579plusmn11510plusmn08810plusmn16910plusmn1398plusmn082

3c5plusmn0493plusmn0412plusmn0458plusmn0868plusmn0995plusmn127

9plusmn1

5plusmn0745plusmn1358plusmn0623plusmn16

3plusmn074



4c10plusmn0775plusmn1558plusmn11514plusmn09414plusmn04912plusmn10313plusmn111plusmn10612plusmn19615plusmn1413plusmn12512plusmn095

Std

15plusmn15915plusmn17914plusmn07416plusmn16916plusmn20514plusmn06115plusmn10115plusmn13514plusmn09516plusmn29515plusmn21613plusmn131

Stdstre

ptom

ycin


Table2In

vitro

antifun

galactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Aniger

Aoryzae

Aterreus

Aflavus

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500


3b14plusmn2212plusmn17812plusmn08214plusmn18512plusmn15712plusmn10510plusmn1638plusmn1393plusmn1315plusmn09

3plusmn1392plusmn054

3c4plusmn2364plusmn0965plusmn11113plusmn11912plusmn10511plusmn1275plusmn1536plusmn097

8plusmn1

10plusmn14410plusmn0629plusmn136


4b5plusmn1352plusmn0692plusmn0915plusmn0825plusmn14

5plusmn10315plusmn17213plusmn16811plusmn1076plusmn11

2plusmn0962plusmn07


Std


Stdflucon

azole


002040608

112141618

2

25 50 75 100

Redu

cing

capa

city

3a3b3c4a4b

4cBHATBHQAA


Figure 3 Ferric (Fe3+) ions reducing capacity of the compounds (3-4)

decomposing lipid hydroperoxides into peroxy and alkoxyradicals that can themselves gain hydrogen and perpetuatethe chain reaction of lipid peroxidation [35 36]

Fe2+ +H2O2997888rarr Fe3+ +OHminus +OH∙ (1)

Determination of ferrous ion (Fe2+) chelating activity ofthe synthesized compounds was carried out as described inDinisrsquo method [37] using BHA TBHQ and AA as standards(Figure 4) Compounds 3a 3b 3c and 4a showed promisingmetal chelating activity (7521 7437 7011 and 7270) at75 120583gmL and (7827 7548 7409 and 7242) at 100 120583gmLconcentration respectively The compound 3b showed goodactivity (7270) at 50120583gmL concentration Differences instandard deviation were estimated by the help of ANOVAs(Tukey) using GraphPad instat software and MS-Excel

3 Conclusion

In this study we have demonstrated the synthesis of somenovel indole derivatives incorporating 5H-dibenzo[bf]aze-pine and thiazolidine heterocycles in a single structure Someof the chloro- and methyl-substituted compounds exhibitedpromising antimicrobial and antioxidant activities

4 Experimental Protocols

All reagents were obtained commercially and used by furtherpurificationMelting points were determined by an open cap-illarymethod and uncorrectedmelting points are reported inthis study Purity of the compounds was checked by thin layerchromatography (TLC) using silica gel-G coated aluminiumplates (Merck) and spots were visualized by exposing thedry plates to iodine vapours The infrared (IR) (KBr) spectrawere recorded with a Perkin-Elmer spectrum one Fourier

0102030405060708090

100110

25 50 75 100

Inhi

bitio

n (

)


3a3b3c4a4b

4cBHATBHQAA

Figure 4 Metal chelating activity of the compounds (3-4)

transform infrared spectroscopy (FT-IR) spectrometer The1Hnuclear magnetic resonance (NMR) (dimethysulphoxide-1198896) spectra were recorded on Bruker NMR (500MHz) and

the chemical shiftswere expressed in parts permillions (ppm)(120575 scale) downfield from tetramethylsilane (TMS) as internalstandard Mass spectra were recorded with a JEOL GCMATEII GC-MSmass spectrometer Elemental analysis was carriedout using Flash EA 1112 series elemental analyzer

5H-Dibenzo[bf]azepine-5-carbohydrazide (1) Was Preparedby the Following Reported Method [26] A mixture of 5H-dibenzo[bf]azepine-5-carbonyl chloride (001mol) and hy-drazine hydrate (001mol 80) in absolute alcohol wasstirred for 2 hrs and then refluxed for 30mins The prod-uct obtained was filtered washed with cold alcohol driedand purified by recrystallization in methanol to give 5H-dibenzo[bf]azepine-5-carbohydrazide (1)

5-Substituted 2-Phenyl Indol-3-carboxyaldehydes (2andash2c)Were Prepared by the Following Literature Procedure [27] Asolution of 5-substituted 2-phenyl-1H-indoles (001mol) inminimum amount of dimethyl formamide was added to aVilsmeier-Haack complex prepared from phosphorous oxy-chloride (1mL) and dimethyl formamide (315mL) main-taining the temperature between 10 and 20∘C The reactionmixture was kept at 45∘C for 30min and poured into icewater (100mL) containing sodium hydroxide (20mL 10)This was boiled for 1min cooled to room temperature fil-tered washedwithwater dried and recrystallized in 14-diox-ane to give 2andash2c

41 General Procedure for the Synthesis of N-[(51015840-Substituted21015840-Phenyl-1H-indol-31015840-yl)methylene]-5H-dibenzo[bf]azepine-5-carbohydrazides (3andash3c) A solution of 1 (001mol) and5-substituted 2-phenylindole-3-carboxyaldehydes (2andash2c)(001mol) in 14-dioxane (40mL) containing glacial aceticacid (2mL) was refluxed for 8 hrs The excess of solvent was


removed under reduced pressure The reaction mixture wascooled to room temperature and poured into ice-cold waterThe separated product was filtered washed thoroughly withcold water dried and recrystallized in ethanol to give 3andash3c

N-[(51015840-Chloro-21015840-phenyl-1H-indol-31015840-yl)methylene]-5H-diben-zo[bf]azepine-5-carbohydrazide (3a) Yellow crystals Yield63 mp 281ndash82∘C Rf 075 ethyl acetate benzene (6 4) IR(KBr) ]cmminus1 3419 (indole NH) 3210 (NH) 1627 (C=O)1574 (C=N) 1H NMR (DMSO-d

6) 120575 1240 (s 1H indole

NH) 930 (s 1H NH) 880 (s 1H N=CH) 670ndash830 (m18H Ar-H) Mass mz 488 (M+) 490 (M++2) Anal Calcdfor C

30H21N4OCl C 7369 H 433 N 1146 Found C

7375 H 428 N 1139

N-[(51015840-Methyl-21015840-phenyl-1H-indol-31015840-yl)methylene]-5H-diben-zo[bf]azepine-5-carbohydrazide (3b)Colorless needles Yield79 mp 221ndash22∘C Rf 075 ethyl acetate benzene (7 3) IR(KBr) ]cmminus1 3413 (indole NH) 3200 (NH) 1625 (C=O)1582 (C=N) 1H NMR (DMSO-d

6) 120575 1238 (s 1H indole

NH) 920 (s 1H NH) 900 (s 1H N=CH) 700ndash810 (m 18HAr-H) 230 (s 3H CH

3) Anal Calcd for C

31H24N4O C

7946 H 516 N 1196 Found C 7936 H 520 N 1200

N-[(21015840-Phenyl-1H-indol-31015840-yl)methylene]-5H-dibenzo[bf]aze-pine-5-carbohydrazide (3c)White solid Yield 65mp above300∘C Rf 052 ethylacetate benzene (4 6) IR (KBr) ]cmminus13405 (indole NH) 3219 (NH) 1618 (C=O) 1570 (C=N) 1HNMR (DMSO-d

6) 120575 1225 (s 1H indole NH) 930 (s 1H

NH) 900 (s 1H N=CH) 705ndash820 (m 19H Ar-H) AnalCalcd for C

30H22N4O C 7927 H 488 N 1233 Found C

7932 H 493 N 1228

42 General Procedure for the Synthesis of N-[2-(51015840-Substi-tuted 21015840-Phenyl-1H-indol-31015840-yl)-4-oxothiazolidin-3-yl]-5H-di-benzo[bf]azepine-5-carboxamides (4andash4c) Amixture of com-pounds 3a 3b and 3c (001mol) and thioglycolic acid (001mol) containing a pinch of anhydrous zinc chloride in DMF(30mL) was refluxed for 8 hrs The mixture was then cooledto room temperature and poured into ice-cold water Theseparated product was filtered washedwith saturated sodiumcarbonate solution to remove unreacted thioglycolic acidfollowed by cold-water dried and recrystallized in ethanolto get pure 4andash4c

N-[2-(51015840-Chloro-21015840-phenyl-1H-indol-31015840-yl)-4-oxothiazolidin-3-yl]-5H-dibenzo[bf]azepine-5-carboxamide (4a)Yellow sol-id Yield 84 mp 201ndash02∘C Rf 065 ethylacetate methanol(1 2) IR (KBr) ]cmminus1 3410 (indole NH) 3131 (NH) 1732(C=O) 1626 (C=O) 1H NMR (DMSO-d

6) 120575 1230 (s 1H

indole NH) 928 (s 1H NH) 690ndash830 (m 18H Ar-H) 470(s 1H CHN) 390 (s 2H CH

2CO) Massmz 562 (M+) 564

(M++2) Anal Calcd for C32H23N4O2SCl C 6826 H 412

N 995 Found C 6832 H 410 N 1000

N-[2-(51015840-Mehyl-21015840-phenyl-1H-indol-31015840-yl)-4-oxothiazolidin-3-yl]-5H-dibenzo[bf]azepine-5-carboxamide (4b)White sol-id Yield 89 mp above 300∘C Rf 065 ethylacetate meth-anol (1 1) IR (KBr) ]cmminus1 3400 (indole NH) 3154 (NH)

1710 (C=O) 1605 (C=O) 1H NMR (DMSO-d6) 120575 1240 (s

1H indole NH) 935 (s 1H NH) 700ndash800 (m 18H Ar-H)500 (s 1H CHN) 380 (s 2H CH

2CO) 225 (s 3H CH

3)

Anal Calcd for C33H26N4O2S C 7304 H 483 N 1032

Found C 7300 H 490 N 1025

N-[2-(21015840-Phenyl-1H-indol-31015840-yl)-4-oxothiazolidin-3-yl]-5H-di-benzo[bf]azepine-5-carboxamide (4c) Yellow solid Yield65 mp 264ndash65∘C Rf 071 ethylacetate methanol (6 4) IR(KBr) ]cmminus1 3400 (indole NH) 3205 (NH) 1725 (C=O)1610 (C=O) 1H NMR (DMSO-d

6) 120575 1210 (s 1H indole

NH) 940 (s 1H NH) 710ndash825 (m 19H Ar-H) 470 (s 1HCHN) 358 (s 2H CH

2CO) Anal Calcd for C

32H24N4O2S

C 7271 H 458 N 1060 Found C 7285 H 463 N1050

5 Biological Activities

51 Antimicrobial Activities The in vitro biological screeningof the synthesized compounds (3 and 4) was carried outagainst bacterial species E coli S aureus K pneumonia andP aeruginosa and fungal speciesA nigerA oryzaeA terreusand A flavus by cup-plate method [28] using nutrient agarand PDA medium for antibacterial and antifungal activitiesrespectively The holes of 6mm diameter were punchedcarefully using a sterile cork borer and these were filled withtest solution (1000 750 and 500 120583gmL in DMF) standardsolution (1000 750 and 500120583gmL in DMF) and DMF ascontrol The plates were incubated at 37∘C for 24 hours and72 hours for the evaluation of antibacterial and antifungalactivities respectively The diameter of the inhibition zonesfor all the test compounds was measured (in mm) andthe results were compared with the results obtained byusing streptomycin and fluconazole as positive standard forantibacterial and antifungal activities respectively

52 Antioxidant Activity Assay

521 11-Diphenyl-2-picryl Hydrazyl (DPPH) Radical Scav-enging Activity (RSA) The radical scavenging activity (RSA)of test compounds (3 and 4) in methanol at different con-centrations (25 50 75 and 100 120583gmL) containing freshlyprepared DPPH in methanol (0004 wv) was carried outand the results were compared with the results obtained byusing standards (BHA TBHQ and AA) by Hatanorsquos method[30] All analyses were performed in three replicates andresults were reported as averaged of three replicates Theresults in percentage are expressed as the ratio of absorbanceof DPPH solutions measured at 517 nm in the presence andthe absence of test compounds by using ELICO SL171 minispec spectrometer The results are shown in Figure 2 Thepercentages of DPPH free radical scavenging activity of thesamples were determined using the following equation

DPPH radical scavenging =119860119888minus 119860119904

119860119888

times 100 (2)

where 119860119888= absorbance of control 119860

119904= absorbance of test

sample


522 Ferric Ions (Fe3+) Reducing Antioxidant Power (FRAP)The reducing power of the synthesized compounds (3 and 4)was determined according to the Oyaizu method [33] Dif-ferent concentrations of samples (25 50 75 and 100 120583gmL)in DMSO (1mL) were mixed with phosphate buffer (25mL02M pH 66) and potassium ferricyanide (25mL 1 wv)The mixture was incubated at 50∘C for 20min A portionof trichloroacetic acid (25mL 10wv) was then added tothe mixture and the mixture was centrifuged for 10min at1000timesgThe upper layer of solution (25mL) was mixed withdistilled water (25mL) and ferric chloride (05mL 01 wv)Absorbance at 700 nm was then measured in spectropho-tometer Higher absorbance of the reactionmixture indicatedgreater reducing power The results are shown in Figure 3

523 Ferrous Ions (Fe2+) Metal Chelating Activity The fer-rous ion chelating activities of synthesized compounds (3 and4) and standards were estimated using the method reportedby Dinis and colleagues [37] The test samples (25 50 75and 100 120583gmL) in ethanol (04mL) were added to ferrouschloride (005mL 2mM) prepared in ethanol The reactionwas initiated by the addition of ferrozine (02mL 5mM)and the volume was adjusted to 35mL with ethanol and05mL water so as to make the final total volume 40mLFerrozine reacts with the divalent iron to form stablemagentacomplex species that were very soluble in water The mixturewas shaken vigorously and kept at room temperature for10min Then the absorbance of the solution was measuredspectrophotometrically at 562 nm All analyses were run inthree triplicates and results are reported as the averagesof three replicates The results are shown in Figure 4 Thepercent inhibition of the ferrozine-Fe2+ complex formationwas calculated using the formula

Ferrous ion chelating effect =119860119888minus 119860119904

119860119888

times 100 (3)



sample

Conflict of Interests

Since The authors have procured the IR NMR and massspectra of the synthesized compounds from the SophisticatedAnalytical Instrument facility namely The Indian Instituteof Technology Madras Chennai India as per the conditionof institution authors should acknowledge their services inthe research paper while publishing the work which includesthe data provided by them in the research paper The samehas been acknowledged in the acknowledgment section Theauthors do not have any agreement financial assistance orsponsorship from Perkin-Elmer spectrum Brucker NMRand so forthThese names are mentioned in the experimentalprotocol as these are the instrument models and it is manda-tory for authors to mention the instrument models usedto scan the spectra of unknown compounds Otherwise thecorresponding author or coauthors have nodirect financialrelationship with the commercial identity mentioned in theirpaper in any form

Acknowledgments

The authors are thankful to the Chairman Departmentof Chemistry Gulbarga University Gulbarga for provid-ing laboratory facilities to the Chairman Department ofMicrobiology Gulbarga University Gulbarga for providingfacilities to carry out antimicrobial activity tests and to theDirector Indian Institute of Technology Madras Chennaifor providing spectral data Vijaykumar Tukaram Katkaris thankful to University grants Commission New DelhiIndia for providing financial assistance through ResearchFellowship in Science Meritorious Students (RFSMS)

References

[1] S Biswal U Sahoo S Sethy H K S Kumar and M BanerjeeldquoIndole the molecule of diverse biological activitiesrdquo AsianJournal of Pharmaceutical and Clinical Research vol 5 no 1 pp1ndash6 2012

[2] S Sibel ldquoAntioxidant activities of synthetic indole derivativesand possible activity mechanismsrdquo Topics in Heterocyclic Chem-istry vol 11 pp 145ndash178 2007

[3] R S Varma and P K Garg ldquoSynthesis of substituted 5-chloro-3-phenylthio-semicarbazono-2-indolinones as potential antimi-crobial agentsrdquo Acta Pharmaceutica Jugoslavica vol 30 no 4pp 199ndash204 1980

[4] S P Singh V A Singh and K G Gupta ldquoSynthesis of somenew 5-bromo-3-arylthiosemicarbazono-2-indolinones as anti-mocrobial agentsrdquo Acta Pharmaceutica Jugoslavica vol 36 no1 pp 19ndash26 1986

[5] M G Bhovi and G S Gadaginamath ldquo13-Dipolar cycload-dition reaction synthesis and antimicrobial activity of somenew 3-ethoxycarbonyl-5-methoxy-6-bromo-2-triazolylmethy-lindolesrdquo Indian Journal of Heterocyclic Chemistry vol 14 no1 pp 15ndash18 2004

[6] D Tan R J Reiter L C Manchester et al ldquoChemical andphysical properties and potential mechanisms melatonin as abroad spectrum antioxidant and free radical scavengerrdquoCurrentTopics in Medicinal Chemistry vol 2 no 2 pp 181ndash197 2002

[7] M A Jordan and L Wilson ldquoMicrotubules as a target foranticancer drugsrdquoNature Reviews Cancer vol 4 no 4 pp 253ndash265 2004

[8] D Garcıa Gimenez E Garcıa Prado T Saenz Rodrıguez AFernandez Arche and R De La Puerta ldquoCytotoxic effect ofthe pentacyclic oxindole alkaloid mitraphylline isolated fromuncaria tomentosa bark on human ewingrsquos sarcoma and breastcancer cell linesrdquo PlantaMedica vol 76 no 2 pp 133ndash136 2010

[9] M R Bell T E DrsquoAmbra V Kumar et al ldquoAntinociceptive(aminoalkyl)indolesrdquo Journal of Medicinal Chemistry vol 34no 3 pp 1099ndash1110 1991

[10] J D Fischer M H Song A B Suttle et al ldquoComparison ofzafirlukast (Accolate) absorption after oral and colonie admin-istration in humansrdquo Pharmaceutical Research vol 17 no 2 pp154ndash159 2000

[11] I A Leneva R J Russell Y S Boriskin and A J Hay ldquoCharac-teristics of arbidol-resistant mutants of influenza virus impli-cations for the mechanism of anti-influenza action of arbidolrdquoAntiviral Research vol 81 no 2 pp 132ndash140 2009

[12] A H Rosengren R Jokubka D Tojjar et al ldquoOverexpression ofAlpha2A-Adrenergic receptors contributes to type 2 diabetesrdquoScience vol 327 no 5962 pp 217ndash220 2010


[13] W Schindler US Patent 2 948 718 1960[14] H D Revanasiddappa B Vijaya L Shivakumar and K Shiva

Prasad ldquoSynthesis characterization and antimicrobial activityof Cu(ii) Co(ii) Ni(ii) Mn(ii) complexes with desipraminerdquoWorld Journal of Chemistry vol 5 no 1 pp 18ndash25 2010

[15] H Vijay Kumar C R Gnanendra and N Naik ldquoSynthesis ofamino acid analogues of 5H-dibenz[bf]azepine and evaluationof their radical scavenging activityrdquo E-Journal of Chemistry vol6 no 1 pp 125ndash132 2009

[16] V K Honnaiah R R Ambati V Sadineni and N Naik ldquoEval-uation of in vitro antioxidant activity of 5H-dibenz[bf]azepineand its analoguesrdquo Journal of Physical Science vol 21 no 1 pp79ndash92 2010

[17] G K Rao R Kaur and P N Sanjay Pai ldquoSynthesis and bio-logical evaluation of dibenzo[bf]azepine-5-carboxylic acid[1-(substituted-phenyl)-ethylidene]-hydrazidesrdquo Der PharmaChemica vol 3 no 3 pp 323ndash329 2011

[18] S L Nawale and A S Dhake ldquoSynthesis and evaluation ofnovel thiazolidinedionederivatives for antibacterial activityrdquoDer Pharma Chemica vol 4 no 6 pp 2270ndash2277 2012

[19] S Malik P K Upadhyaya and S Miglani ldquoThiazolidinedionesa plethro of biological loadrdquo International Journal of PharmTechResearch vol 3 no 1 pp 62ndash75 2011

[20] S P Kushwaha R Sunil Kumar P Kumar Abhishek and KTripathi ldquoCoupling antioxidant and antidiabetic assets of 2 4-thiazolidinedione derivativesrdquo Asian Journal of PharmaceuticalAnalysis vol 1 no 4 pp 71ndash73 2011

[21] M Cacic MMolnar B Sarkanj E Has-Schon and V RajkovicldquoSynthesis and antioxidant activity of some new coumarinyl-13-thiazolidine- 4-onesrdquo Molecules vol 15 no 10 pp 6795ndash6809 2010

[22] A R Saundane and P Walmik ldquoSynthesis antioxidant antimi-crobial antimycobacterial and cytotoxic activities of azetidi-none and thiazolidinone moieties linked to indole nucleusrdquoJournal of Chemistry vol 2013 Article ID 543815 9 pages 2013

[23] A R Saundane V Katkar and A V Vaijinath ldquoSynthesisandantioxidant and antimicrobial activities of N-[(5rsquo-substituted-2rsquo-phenyl-1H-indol-3rsquo-yl)methylene]-5-(pyridin-4-yl)-134-oxadiazol-2-aminesrdquo Journal of Chemistry 2013

[24] A R Saundane A V Vaijinath and V Katkar ldquoSynthesisantimicrobial and antioxidant activities of some novel n-[(5-substituted 2-phenylindol-3-yl)methylene]-4-phenylthiazol-2-amine derivativesrdquo Indian Journal Heterocyclic Chemistry vol22 pp 127ndash134 2012

[25] A R Saundane M Yarlakatti Pr Walmik and V KatkarldquoSynthesis antioxidant and antimicrobial evaluation of thi-azolidinone azetidinone encompassing indolylthienopyrim-idinesrdquo Journal of Chemical Science vol 124 no 2 pp 469ndash4812012

[26] K Ranjit G K Rao and P N S Pai ldquoSynthesis and bio-logical evaluation of N1-[(3z)-5-substituted-2-Oxo-l 2-Dihy-dro3H-Indol-3-Ylidene]-5H-Dibenzo[bf] Azepine-5-Carbo-hydrazidesrdquo International Journal of Biological Chemistry vol4 no 1 pp 19ndash26 2010

[27] S P Hiremath J S Biradar and M G Purohit ldquoA new route toindolo [32-b]isoquinolinesrdquo Indian Journal of Chemistry B vol21 pp 249ndash253 1982

[28] Indian Pharmacopeia New Delhi Appendix IV Government ofIndia New Delhi India 3rd edition edition 1985

[29] S Vertuani A Angusti and S Manfredini ldquoThe antioxidantsand pro-antioxidants network an overviewrdquo Current Pharma-ceutical Design vol 10 no 14 pp 1677ndash1694 2004

[30] T Hatano H Kagawa T Yasuhara and T Okuda ldquoTwo newflavonoids and other constituents in licorice root their relativeastringency and radical scavenging effectsrdquo Chemical and Phar-maceutical Bulletin vol 36 no 6 pp 2090ndash2097 1988

[31] M Strlic T Radovic J Kolar and B Pihlar ldquoAnti- and pro-oxidative properties of gallic acid in fenton-type systemsrdquoJournal of Agricultural and Food Chemistry vol 50 no 22 pp6313ndash6317 2002

[32] I Clis M Hosny T Khalifa and S Nishibe ldquoSecoiridoids fromFraxinus angustifoliardquo Phytochemistry vol 33 no 6 pp 1453ndash1456 1993

[33] M Oyaizu ldquoStudies on products of the browning reactionAntioxidative activities of browning reactionproducts preparedfromglucosaminerdquo Japanese Journal of Nutrition vol 44 no 6pp 307ndash315 1986

[34] I Gulcin M Elmastas and H Y Aboul-Enein ldquoDeterminationof antioxidant and radical scavenging activity of basil (Ocimumbasilicum L Family Lamiaceae) assayed by different method-ologiesrdquo Phytotherapy Research vol 21 no 4 pp 354ndash361 2007

[35] I Gulcin H A Alici and M Cesur ldquoDetermination of invitro antioxidant and radical scavenging activities of propofolrdquoChemical and Pharmaceutical Bulletin vol 53 no 3 pp 281ndash285 2005

[36] B Halliwell ldquoReactive oxygen species in living systems sourcebiochemistry and role in human diseaserdquo American Journal ofMedicine vol 91 supplement 3 pp S14ndashS22 1991

[37] T C P Dinis V M C Madeira and L M Almeida ldquoActionof phenolic derivatives (acetaminophen salicylate and 5-aminosalicylate) as inhibitors of membrane lipid peroxidationand as peroxyl radical scavengersrdquo Archives of Biochemistry andBiophysics vol 315 no 1 pp 161ndash169 1994

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy


Carbohydrate Chemistry

International Journal of


Journal of

Chemistry


Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of


The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of


Chromatography Research International


Applied ChemistryJournal of



Theoretical ChemistryJournal of


Journal of

Spectroscopy

Analytical ChemistryInternational Journal of


Journal of


Quantum Chemistry


Organic Chemistry International

ElectrochemistryInternational Journal of



CatalystsJournal of


S

NN S

O

R

S

NN S

NH

O

R

N

N N

ON S

NHNH

O

NH

Ph

NSN

N

S

OO

1 2

3 4

R

H3C

H3C

CH3

Figure 1 Motivation for synthesis of antimicrobial and antioxidant active compounds

2-(5-substituted-2-phenyl-1H-indol-3-yl)-3-(5-(pyridin-4-yl)-134-oxadiazol-2-yl)thiazolidin-4-ones (2) [23] 2-(5-sub-stituted-2-phenyl-1H-indol-3-yl)-3-(4-phenylthiazol-2-yl)thi-azolidin-4-ones (3) [24] and 256-trimethyl-3-[2-(2-phenyl-5-substituted-1H-indol-3-yl)-4-oxothiazolidin-3-yl]thieno[23-d]pyrimidin-4(3H)-ones (4) [25] (Figure 1) Prompted bythese results we herein report the synthesis of title com-pounds and the evaluation of their antimicrobial and anti-oxidant activities

2 Result and Discussion

Thepathway for the synthesis of title compounds is illustratedin Scheme 1 Cyclocondensation of 5H-dibenzo[bf]azepine-5-carbohydrazide (1) [26] with 5-chloro-2-phenyl-1H-indol-3-carboxaldehyde (2a) [27] gave the intermediate N-[(51015840-chloro-21015840-phenyl-1H-indol-31015840-yl)methylene]-5H-dibenzo[bf]azepine-5-carbohydrazide (3a) Further compound (3a)on refluxing with thioglycolic acid afforded N-[2-(51015840-sub-stituted-21015840-phenyl-1H-indol-31015840-yl)-4-oxothiazolidin-3-yl]-5H-dibenzo[bf]azepine-5-carboxamide (4a) The structures ofall these previously unknown compounds were characterizedby spectral studies and elemental analysis

21 Antimicrobial Activities All the synthesized compounds(3 and 4) were evaluated for their antibacterial activityagainst Escherichia coli (MTCC-723) Staphylococcus aureus(ATCC-29513) Klebsiella pneumoniae (NCTC-13368) andPseudomonas aeruginosa (MTCC-1688) and antifungal activ-ity against Aspergillus niger (MTCC-281) Aspergillus oryzae(MTCC-3567T)Aspergillus terreus (MTCC-1782) andAsper-gillus flavus (MTCC-1973) by cup-plate method [28] Thezone of inhibition (in mm) was compared with the inhibi-tion zones obtained using streptomycin and fluconazole as

positive controls for antibacterial and antifungal activitiesrespectively The results are tabulated in Tables 1 and 2

Antibacterial screening revealed that compound 4a hav-ing chloro substitution at C-5 position of indole and diben-zo[bf]azepine ring along with thiazolidine system showedthemaximum inhibition against S aureusK pneumonia andP aeruginosa at all concentrations Compound 3a exhibitedmaximum inhibition against K pneumoniae due to the pres-ence of chloro substitution at C-5 position whereas com-pounds 3b and 4b showed maximum inhibition against Saureus and E coli respectively

Antifungal activity assay revealed that the compounds 3aand 4a exhibited maximum inhibition against A niger Aoryzae andA flavusThis enhanced activity of 3a and 4amaybe due to the presence of chloro substitution atC-5 position ofindole ring Also compound 4a showed good activity againstA terreus Compound 3b exhibited higher activity againstA niger A oryzae and A flavus at all concentrations Asdeduced from above stated results in general the presenceof the chloro or methyl substitution at C-5 position ofindole enhanced the activity of the compounds Differencesin standard deviation were calculated by means of ANOVAs(Tukey) using GraphPad instat software

22 Antioxidant Activities

221 11-Diphenyl-2-picryl Hydrazyl (DPPH) Radical Scaveng-ing Activity (RSA) Antioxidants are intimately involved inthe prevention of cellular damage cancer aging and a varietyof diseases DPPH is stable free radical that can accept anelectron or hydrogen atom and its stability originates fromdelocalization of the unpaired electron over the molecule

Free radicals are highly reactive species with one ormore unpaired electrons in their last orbital Reactive oxy-gen species (ROS) important in biological systems include


N

O

N

NH

NNH

O

N

NH

NNH

O

R

S

O

NH

CHO

1

3andashc4andashc

2andashc


NHNH2

HSCH2COOH

+

R

R


superoxide (O2


2O2)


2) Once formed ROS





0102030405060708090

100

25 50 75 100

Inhi

bitio

n (

)


3a3b3c4a4b

4cBHATBHQAA





Table1In

vitro

antib

acteria

lactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Ecoli

Saureus

Kpn

eumoniae

Paeruginosa

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500




9plusmn1


3plusmn074




Std


Stdstre

ptom

ycin


Table2In

vitro

antifun

galactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Aniger

Aoryzae

Aterreus

Aflavus

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500





8plusmn1





2plusmn0962plusmn07


Std


Stdflucon

azole


002040608

112141618

2

25 50 75 100

Redu

cing

capa

city

3a3b3c4a4b

4cBHATBHQAA






3 Conclusion




0102030405060708090

100110

25 50 75 100

Inhi

bitio

n (

)


3a3b3c4a4b

4cBHATBHQAA










6) 120575 1240 (s 1H indole


30H21N4OCl C 7369 H 433 N 1146 Found C

7375 H 428 N 1139


6) 120575 1238 (s 1H indole


3) Anal Calcd for C

31H24N4O C

7946 H 516 N 1196 Found C 7936 H 520 N 1200


6) 120575 1225 (s 1H indole NH) 930 (s 1H


30H22N4O C 7927 H 488 N 1233 Found C

7932 H 493 N 1228



6) 120575 1230 (s 1H


2CO) Massmz 562 (M+) 564


N 995 Found C 6832 H 410 N 1000


1710 (C=O) 1605 (C=O) 1H NMR (DMSO-d6) 120575 1240 (s


2CO) 225 (s 3H CH

3)


Found C 7300 H 490 N 1025


6) 120575 1210 (s 1H indole



32H24N4O2S

C 7271 H 458 N 1060 Found C 7285 H 463 N1050






119860119888

times 100 (2)



sample





119860119888

times 100 (3)



sample



Acknowledgments


References
















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


N

O

N

NH

NNH

O

N

NH

NNH

O

R

S

O

NH

CHO

1

3andashc4andashc

2andashc


NHNH2

HSCH2COOH

+

R

R


superoxide (O2


2O2)


2) Once formed ROS





0102030405060708090

100

25 50 75 100

Inhi

bitio

n (

)


3a3b3c4a4b

4cBHATBHQAA





Table1In

vitro

antib

acteria

lactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Ecoli

Saureus

Kpn

eumoniae

Paeruginosa

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500




9plusmn1


3plusmn074




Std


Stdstre

ptom

ycin


Table2In

vitro

antifun

galactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Aniger

Aoryzae

Aterreus

Aflavus

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500





8plusmn1





2plusmn0962plusmn07


Std


Stdflucon

azole


002040608

112141618

2

25 50 75 100

Redu

cing

capa

city

3a3b3c4a4b

4cBHATBHQAA






3 Conclusion




0102030405060708090

100110

25 50 75 100

Inhi

bitio

n (

)


3a3b3c4a4b

4cBHATBHQAA










6) 120575 1240 (s 1H indole


30H21N4OCl C 7369 H 433 N 1146 Found C

7375 H 428 N 1139


6) 120575 1238 (s 1H indole


3) Anal Calcd for C

31H24N4O C

7946 H 516 N 1196 Found C 7936 H 520 N 1200


6) 120575 1225 (s 1H indole NH) 930 (s 1H


30H22N4O C 7927 H 488 N 1233 Found C

7932 H 493 N 1228



6) 120575 1230 (s 1H


2CO) Massmz 562 (M+) 564


N 995 Found C 6832 H 410 N 1000


1710 (C=O) 1605 (C=O) 1H NMR (DMSO-d6) 120575 1240 (s


2CO) 225 (s 3H CH

3)


Found C 7300 H 490 N 1025


6) 120575 1210 (s 1H indole



32H24N4O2S

C 7271 H 458 N 1060 Found C 7285 H 463 N1050






119860119888

times 100 (2)



sample





119860119888

times 100 (3)



sample



Acknowledgments


References
















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


Table1In

vitro

antib

acteria

lactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Ecoli

Saureus

Kpn

eumoniae

Paeruginosa

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500




9plusmn1


3plusmn074




Std


Stdstre

ptom

ycin


Table2In

vitro

antifun

galactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Aniger

Aoryzae

Aterreus

Aflavus

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500





8plusmn1





2plusmn0962plusmn07


Std


Stdflucon

azole


002040608

112141618

2

25 50 75 100

Redu

cing

capa

city

3a3b3c4a4b

4cBHATBHQAA






3 Conclusion




0102030405060708090

100110

25 50 75 100

Inhi

bitio

n (

)


3a3b3c4a4b

4cBHATBHQAA










6) 120575 1240 (s 1H indole


30H21N4OCl C 7369 H 433 N 1146 Found C

7375 H 428 N 1139


6) 120575 1238 (s 1H indole


3) Anal Calcd for C

31H24N4O C

7946 H 516 N 1196 Found C 7936 H 520 N 1200


6) 120575 1225 (s 1H indole NH) 930 (s 1H


30H22N4O C 7927 H 488 N 1233 Found C

7932 H 493 N 1228



6) 120575 1230 (s 1H


2CO) Massmz 562 (M+) 564


N 995 Found C 6832 H 410 N 1000


1710 (C=O) 1605 (C=O) 1H NMR (DMSO-d6) 120575 1240 (s


2CO) 225 (s 3H CH

3)


Found C 7300 H 490 N 1025


6) 120575 1210 (s 1H indole



32H24N4O2S

C 7271 H 458 N 1060 Found C 7285 H 463 N1050






119860119888

times 100 (2)



sample





119860119888

times 100 (3)



sample



Acknowledgments


References
















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


Table2In

vitro

antifun

galactivities

ofthec

ompo

unds

3-4

Com

poun

dnu

mber

Aniger

Aoryzae

Aterreus

Aflavus

Con

c(120583gmL)

(diameterso

finh

ibition

inmm)

1000

750

500

1000

750

500

1000

750

500

1000

750

500





8plusmn1





2plusmn0962plusmn07


Std


Stdflucon

azole


002040608

112141618

2

25 50 75 100

Redu

cing

capa

city

3a3b3c4a4b

4cBHATBHQAA






3 Conclusion




0102030405060708090

100110

25 50 75 100

Inhi

bitio

n (

)


3a3b3c4a4b

4cBHATBHQAA










6) 120575 1240 (s 1H indole


30H21N4OCl C 7369 H 433 N 1146 Found C

7375 H 428 N 1139


6) 120575 1238 (s 1H indole


3) Anal Calcd for C

31H24N4O C

7946 H 516 N 1196 Found C 7936 H 520 N 1200


6) 120575 1225 (s 1H indole NH) 930 (s 1H


30H22N4O C 7927 H 488 N 1233 Found C

7932 H 493 N 1228



6) 120575 1230 (s 1H


2CO) Massmz 562 (M+) 564


N 995 Found C 6832 H 410 N 1000


1710 (C=O) 1605 (C=O) 1H NMR (DMSO-d6) 120575 1240 (s


2CO) 225 (s 3H CH

3)


Found C 7300 H 490 N 1025


6) 120575 1210 (s 1H indole



32H24N4O2S

C 7271 H 458 N 1060 Found C 7285 H 463 N1050






119860119888

times 100 (2)



sample





119860119888

times 100 (3)



sample



Acknowledgments


References
















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


002040608

112141618

2

25 50 75 100

Redu

cing

capa

city

3a3b3c4a4b

4cBHATBHQAA






3 Conclusion




0102030405060708090

100110

25 50 75 100

Inhi

bitio

n (

)


3a3b3c4a4b

4cBHATBHQAA










6) 120575 1240 (s 1H indole


30H21N4OCl C 7369 H 433 N 1146 Found C

7375 H 428 N 1139


6) 120575 1238 (s 1H indole


3) Anal Calcd for C

31H24N4O C

7946 H 516 N 1196 Found C 7936 H 520 N 1200


6) 120575 1225 (s 1H indole NH) 930 (s 1H


30H22N4O C 7927 H 488 N 1233 Found C

7932 H 493 N 1228



6) 120575 1230 (s 1H


2CO) Massmz 562 (M+) 564


N 995 Found C 6832 H 410 N 1000


1710 (C=O) 1605 (C=O) 1H NMR (DMSO-d6) 120575 1240 (s


2CO) 225 (s 3H CH

3)


Found C 7300 H 490 N 1025


6) 120575 1210 (s 1H indole



32H24N4O2S

C 7271 H 458 N 1060 Found C 7285 H 463 N1050






119860119888

times 100 (2)



sample





119860119888

times 100 (3)



sample



Acknowledgments


References
















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of




6) 120575 1240 (s 1H indole


30H21N4OCl C 7369 H 433 N 1146 Found C

7375 H 428 N 1139


6) 120575 1238 (s 1H indole


3) Anal Calcd for C

31H24N4O C

7946 H 516 N 1196 Found C 7936 H 520 N 1200


6) 120575 1225 (s 1H indole NH) 930 (s 1H


30H22N4O C 7927 H 488 N 1233 Found C

7932 H 493 N 1228



6) 120575 1230 (s 1H


2CO) Massmz 562 (M+) 564


N 995 Found C 6832 H 410 N 1000


1710 (C=O) 1605 (C=O) 1H NMR (DMSO-d6) 120575 1240 (s


2CO) 225 (s 3H CH

3)


Found C 7300 H 490 N 1025


6) 120575 1210 (s 1H indole



32H24N4O2S

C 7271 H 458 N 1060 Found C 7285 H 463 N1050






119860119888

times 100 (2)



sample





119860119888

times 100 (3)



sample



Acknowledgments


References
















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of





119860119888

times 100 (3)



sample



Acknowledgments


References
















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of




































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of

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