1H-NMR · Web view2Diseases of the Developing World (DDW), Tres Cantos Medicines Development Campus...
Transcript of 1H-NMR · Web view2Diseases of the Developing World (DDW), Tres Cantos Medicines Development Campus...
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Supporting information
Differential characterization using readily accessible NMR experiments of novel N- and O-alkylated quinolin-4-ol, 1,5-
naphthyridin-4-ol and quinazolin-4-ol derivatives with antimycobacterial activity
Eleni Pitta1, Olga Balabon1, Maciej K. Rogacki1, Jesús Gómez2, Fraser Cunningham2, Koen
Augustyns1, Jurgen Joosens1, Pieter van der Veken1,*, Robert Bates2,*
1Medicinal Chemistry, Department of Pharmaceutical Sciences, University of Antwerp,
Universitieitsplein 1, B-2610 Wilrijk, Belgium
2Diseases of the Developing World (DDW), Tres Cantos Medicines Development Campus
(TCMDC), GlaxoSmithKline, Severo Ochoa 2, 28760, Tres Cantos Madrid, Spain
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Table of ContentsCompound 9a.............................................................................................................................................4
1H-NMR....................................................................................................................................................413C-NMR...................................................................................................................................................4
HSQC........................................................................................................................................................5
HMBC.......................................................................................................................................................6
COSY........................................................................................................................................................7
NOE.........................................................................................................................................................8
Compound 9b..............................................................................................................................................91H-NMR....................................................................................................................................................913C-NMR...................................................................................................................................................9
HSQC......................................................................................................................................................10
HMBC.....................................................................................................................................................11
NOE........................................................................................................................................................12
Compound 9c............................................................................................................................................131H-NMR..................................................................................................................................................1313C-NMR.................................................................................................................................................13
HSQC......................................................................................................................................................14
HMBC.....................................................................................................................................................15
NOE........................................................................................................................................................16
Compound 13a..........................................................................................................................................171H-NMR..................................................................................................................................................1713C-NMR.................................................................................................................................................17
HSQC......................................................................................................................................................18
HMBC.....................................................................................................................................................19
COSY......................................................................................................................................................20
NOE........................................................................................................................................................21
Compound 13b..........................................................................................................................................221H-NMR..................................................................................................................................................2213C-NMR.................................................................................................................................................22
HSQC......................................................................................................................................................23
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HMBC.....................................................................................................................................................24
NOE........................................................................................................................................................25
Compound 17............................................................................................................................................261H-NMR..................................................................................................................................................2613C-NMR.................................................................................................................................................26
HSQC......................................................................................................................................................27
HMBC.....................................................................................................................................................28
Compound 21a..........................................................................................................................................291H-NMR..................................................................................................................................................2913C-NMR.................................................................................................................................................29
HSQC......................................................................................................................................................30
HMBC.....................................................................................................................................................31
COSY......................................................................................................................................................32
NOE........................................................................................................................................................33
Compound 21b..........................................................................................................................................341H-NMR..................................................................................................................................................3413C-NMR.................................................................................................................................................34
HSQC......................................................................................................................................................35
HMBC.....................................................................................................................................................36
NOE........................................................................................................................................................37
Compound 21c..........................................................................................................................................381H-NMR..................................................................................................................................................3813C-NMR.................................................................................................................................................38
HSQC......................................................................................................................................................39
HMBC.....................................................................................................................................................40
NOE........................................................................................................................................................41
Compound 23............................................................................................................................................431H-NMR..................................................................................................................................................4313C-NMR.................................................................................................................................................43
HSQC......................................................................................................................................................44
HMBC.....................................................................................................................................................45
NOE........................................................................................................................................................46
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Compound 9a1H-NMR
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13C-NMR
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HSQC
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HMBC
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COSY
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NOE
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Compound 9b1H-NMR
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13C-NMR
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HSQC
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HMBC
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NOE
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Compound 9c1H-NMR
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13C-NMR
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HSQC
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HMBC
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NOE
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Compound 13a1H-NMR
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13C-NMR
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HSQC
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HMBC
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COSY
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NOE
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Compound 13b1H-NMR
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13C-NMR
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HSQC
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HMBC
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NOE
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Compound 171H-NMR
13C-NMR
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HSQC
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HMBC
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Compound 21a1H-NMR
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13C-NMR
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HSQC
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HMBC
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COSY
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NOE
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Compound 21b1H-NMR
13C-NMR
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HSQC
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HMBC
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NOE
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Compound 21c1H-NMR
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13C-NMR
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HSQC
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HMBC
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COSY
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NOE
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Compound 231H-NMR
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13C-NMR
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HSQC
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HMBC
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NOE