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

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

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

Compound 9a1H-NMR

13C-NMR

HSQC

HMBC

COSY

NOE

Compound 9b1H-NMR

13C-NMR

HSQC

HMBC

NOE

Compound 9c1H-NMR

13C-NMR

HSQC

HMBC

NOE

Compound 13a1H-NMR

13C-NMR

HSQC

HMBC

COSY

NOE

Compound 13b1H-NMR

13C-NMR

HSQC

HMBC

NOE

Compound 171H-NMR

13C-NMR

HSQC

HMBC

Compound 21a1H-NMR

13C-NMR

HSQC

HMBC

COSY

NOE

Compound 21b1H-NMR

13C-NMR

HSQC

HMBC

NOE

Compound 21c1H-NMR

13C-NMR

HSQC

HMBC

COSY

NOE

Compound 231H-NMR

13C-NMR

HSQC

HMBC

NOE