Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents
Prithwiraj De
1, 2
,
Georges Koumba Yoya
1, 2
,
Patricia CONSTANT
1, 3
,
Florence Bedos-Belval
1, 2
,
Hubert Duran
1, 2
,
Nathalie Saffon
1, 4
,
Mamadou Daffé
1, 3
,
Michel Baltas
1, 2
2
CNRS, LSPCMIB (Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique), 118, Route de Narbonne, F-31062 Toulouse Cedex 9, France
|
3
CNRS, IPBS, (Institut de Pharmacologie et Biologie Structurale), Département Mécanismes Moléculaires des Infections Mycobactériennes, 205 route de Narbonne, F-31077 Toulouse Cedex 04, France
|
4
Structure Fédérative Toulousaine en Chimie Moléculaire, FR 2599, 118, Route de Narbonne, F-31062 Toulouse Cedex 9, France
|
Publication type: Journal Article
Publication date: 2011-02-10
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
21309577
Drug Discovery
Molecular Medicine
Abstract
Tuberculosis, HIV coinfection with TB, emergence of multidrug-resistant TB, and extensively drug-resistant TB are the major causes of death from infectious diseases worldwide. Because no new drug has been introduced in the last several decades, new classes of molecules as anti-TB drugs are urgently needed. Herein, we report the synthesis and structure-activity relationships of a series of thioester, amide, hydrazide, and triazolophthalazine derivatives of 4-alkoxy cinnamic acid. Many compounds exhibited submicromolar minimum inhibitory concentrations against Mycobacterium tuberculosis strain (H(37)Rv). Interestingly, compound 13e, a 4-isopentenyloxycinnamyl triazolophthalazine derivative, was found to be 100-1800 times more active than isoniazid (INH) when tested for its ability to inhibit the growth of INH-resistant M. tuberculosis strains. The results also revealed that 13e does not interfere with mycolic acid biosynthesis, thereby pointing to a different mode of action and representing an attractive lead compound for the development of new anti-TB agents.
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De P. et al. Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents // Journal of Medicinal Chemistry. 2011. Vol. 54. No. 5. pp. 1449-1461.
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De P., Koumba Yoya G., CONSTANT P., Bedos-Belval F., Duran H., Saffon N., Daffé M., Baltas M. Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents // Journal of Medicinal Chemistry. 2011. Vol. 54. No. 5. pp. 1449-1461.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jm101510d
UR - https://doi.org/10.1021/jm101510d
TI - Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents
T2 - Journal of Medicinal Chemistry
AU - De, Prithwiraj
AU - Koumba Yoya, Georges
AU - CONSTANT, Patricia
AU - Bedos-Belval, Florence
AU - Duran, Hubert
AU - Saffon, Nathalie
AU - Daffé, Mamadou
AU - Baltas, Michel
PY - 2011
DA - 2011/02/10
PB - American Chemical Society (ACS)
SP - 1449-1461
IS - 5
VL - 54
PMID - 21309577
SN - 0022-2623
SN - 1520-4804
ER -
Cite this
BibTex (up to 50 authors)
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@article{2011_De,
author = {Prithwiraj De and Georges Koumba Yoya and Patricia CONSTANT and Florence Bedos-Belval and Hubert Duran and Nathalie Saffon and Mamadou Daffé and Michel Baltas},
title = {Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents},
journal = {Journal of Medicinal Chemistry},
year = {2011},
volume = {54},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jm101510d},
number = {5},
pages = {1449--1461},
doi = {10.1021/jm101510d}
}
Cite this
MLA
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De, Prithwiraj, et al. “Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents.” Journal of Medicinal Chemistry, vol. 54, no. 5, Feb. 2011, pp. 1449-1461. https://doi.org/10.1021/jm101510d.