3316
M. A. Ali, M. Shaharyar / Bioorg. Med. Chem. Lett. 17 (2007) 3314–3316
All the newly synthesized compounds (1–14) were fur-
ther examined for toxicity (IC ) in a mammalian Vero
and Dr. Kiran Smith, National Cancer Institute-USA,
for valuable suggestion.
5
0
cell line at concentrations of 62.5 lg/mL. After 72 h
exposure, viability was assessed on the basis of cellular
conversion of (MTT) 3-(4,5-dimethylthiozole-2yl)-2,5-
diphenyl tetrazolium bromide into a formazan product
using the Promega Cell Tier 96 non-radioactive cell pro-
liferation assay. These compounds were found to be
non-toxic at 62.5 lg/mL.
Supplementary data
1
3
To summarize, we have synthesized new class of mannich
bases as a novel class of antitubercular agents. The newly
synthesized novel heterocycles exhibited promising myco-
bacterial activities against both drug-sensitive and
drug-resistant strains of Mycobacterium tuberculosis.
Among the compounds (4) 3-{2-furyl[4-(4-{2-furyl[5-
References and notes
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1
2
(
2-naphthyloxymethyl)-2-thioxo-2,3-dihydro-1,3,4-oxa-
diazol-3-yl]methylamino}phenylsulfonyl)anilino]methyl}-
-(2-naphthyloxymethyl)-2,3-dihydro-1,3,4-oxadiazole-2-
thione and (6) 3-[2-Furyl(4-{4-[2-furyl(5-phenoxymethyl-
-thioxo-2,3-dihydro-1,3,4-oxadiazol-3-yl)methylami-
no]phenylsulfonyl} anilino)methyl]-5-phenoxymethyl-
3
. Sbarbaro, J. A. Chest 1997, 111, 1149.
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5
2
5
. Schaberg, T.; Gloger, G.; Reichert, B.; Mauch, H.; Lode,
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1
4
2
agents and more than 5-fold potent than INH against
,3-dihydro-1,3,4-oxadiazole-2-thione were most active
6
. Blair, I. A.; Timoco, R. M.; Brodie, M. J.; Clarc, R. A.;
Dollery, T.; Timbrell, J. A.; Beever, I. A. Hum. Toxicol.
M. tuberculosis H Rv and ꢀ10-fold potent than INH
3
7
1
985, 4, 195.
against INH resistant M. tuberculosis. These results make
novel oxadiazole-substituted mannich bases interesting
lead molecule for more synthetic and biological evalua-
tion. It can be concluded that this class of compounds cer-
tainly hold great promise towards pursuit to discover
novel class of antimycobacterial agents. Further studies
to acquire more information about quantitative struc-
ture–activity relationships are in progress in our
laboratory.
7
. Potts, K.. In Compr. Heterocyclic Chem.; Katritzky, A.
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Acknowledgements
1
The authors express their thanks to University Grant
Commission-New Delhi, India, for the research award,
Dr.V. K Agarwal and Dr.Manju Agarwal, Alwar Phar-
macy College, Alwar, Rajasthan, for providing research
facilities. We thank the Tuberculosis Research Center,
Chennai, India, National Institute of Allergy and Infec-
tions Diseases Southern Research Institute/GW Long
Hansen’s Disease Center, Colorado State University
Birmingham, Alamba, USA, for the necessary help
14. Compounds: (4) IR:(KBr) cm-1: 3400 (NH), 1600 (C@N),
1
1350(C-N), 1250 (S@O), 1150 (C–O–C), 1100 (C@S); H
NMR(DMSO-d
6
) ppm: 4.72(4H, s, CH2, · 2), 6.10 (2H, s,
CH·2), 6.38 (furan, m, 6H), 6.51–7.97 (22H, m, Ar), 10.42
2H, s, NH·2); Ana C48 . (6) IR: (KBr) cm-1:
404 (NH), 1680 (C@N), 1354 (C–N), 1245 (S@O), 1140
(
3
36 6 8 3
H N O S
1
(
6
C–O–C), 1120 (C@S); H NMR (DMSO-d ) ppm: 4.62
(
4H, s, CH · 2), 6.12 (2H, s, CH·2), 6.32 (furan, 6H),
2
,
6
.61–8.0 (18H, m, Ar), 10.12 (2H, s, NH·2); Ana
40 32 6 8 3
C H N O S .