Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents.
Pradip K Gadekar
1
,
H Sivaramakrishnan
1
,
Nishigandha Naik
2
,
Vijay M. Khedkar
3
,
Dhiman Sarkar
4
,
Amit S. Choudhari
4
,
S Mohana Roopan
5
1
Department of Process Development, Piramal Enterprises Ltd., Lighthall A Wing, Hiranandani Business Park, Sakivihar Road, Chandivali, Andheri (East), Mumbai 400072, India
|
2
Haffkine Institute for Training, Research and Testing, Acharya Donde MargParel, Mumbai 400012, India
|
3
Department of Pharmaceutical Chemistry, Shri Vile Parle Kelavani Mandal's Institute of Pharmacy, Mumbai - Agra National Hwy, Dhule, Maharashtra 424001, India.
|
Publication type: Journal Article
Publication date: 2019-05-01
scimago Q1
wos Q1
SJR: 0.786
CiteScore: 8.3
Impact factor: 4.7
ISSN: 00452068, 10902120
PubMed ID:
30776681
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Abstract
Cinnamic acid and its derivatives are known for anti-tubercular activity. The present study reports the synthesis of cinnamic acid derivatives via bioisosteric replacement of terminal carboxylic acid with "oxadiazole". A series of cinnamic acid derivatives (styryl oxadiazoles) were designed and synthesized in good yields by reaction of substituted cinnamic acids (2, 15a-15s) with amidoximes. The synthesized styryl oxadiazoles were evaluated in vitro for anti-tubercular activity against Mycobacterium tuberculosis (Mtb) H37Ra strain. The structure-activity relationship (SAR) study has identified several compounds with mixed anti-tubercular profiles. The compound 32 displayed potent anti-tubercular activity (IC50 = 0.045 µg/mL). Molecular docking studies on mycobacterial enoyl-ACP reductase enzyme corroborated well with the experimental findings providing a platform for structure based hit-to-lead development.
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Atmaram U. A. et al. Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents. // Bioorganic Chemistry. 2019. Vol. 86. pp. 507-512.
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Gadekar P. K., Sivaramakrishnan H., Naik N., Khedkar V. M., Sarkar D., Choudhari A. S., Mohana Roopan S. Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents. // Bioorganic Chemistry. 2019. Vol. 86. pp. 507-512.
Cite this
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TY - JOUR
DO - 10.1016/j.bioorg.2019.01.054
UR - https://doi.org/10.1016/j.bioorg.2019.01.054
TI - Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents.
T2 - Bioorganic Chemistry
AU - Gadekar, Pradip K
AU - Sivaramakrishnan, H
AU - Naik, Nishigandha
AU - Khedkar, Vijay M.
AU - Sarkar, Dhiman
AU - Choudhari, Amit S.
AU - Mohana Roopan, S
PY - 2019
DA - 2019/05/01
PB - Elsevier
SP - 507-512
VL - 86
PMID - 30776681
SN - 0045-2068
SN - 1090-2120
ER -
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@article{2019_Atmaram,
author = {Pradip K Gadekar and H Sivaramakrishnan and Nishigandha Naik and Vijay M. Khedkar and Dhiman Sarkar and Amit S. Choudhari and S Mohana Roopan},
title = {Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents.},
journal = {Bioorganic Chemistry},
year = {2019},
volume = {86},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/j.bioorg.2019.01.054},
pages = {507--512},
doi = {10.1016/j.bioorg.2019.01.054}
}