- Design, synthesis, and biological evaluation of new cinnamic derivatives as antituberculosis agents
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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 (H37Rv). 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.
- De, Prithwiraj,Koumba Yoya, Georges,Constant, Patricia,Bedos-Belval, Florence,Duran, Hubert,Saffon, Nathalie,Daffé, Mamadou,Baltas, Michel
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experimental part
p. 1449 - 1461
(2011/05/05)
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- Synthesis of substituted pyrido[1,2-a]pyrimidines from 2-arylmethylidene-3- fluoroalkyl-3-oxopropionates
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Cyclocondensation of 2-arylmethylidene-3-fluoroalkyl-oxopropionates with 2-amino-pyridine occurs at both the polyfluoroacylvinyl and alkoxycarbonylvinyl fragments to give alkyl 4-aryl-2-polyfluoroalkyl-4H-pyrido[1,2-a]pyrimidine-3- carboxylates and 4-aryl
- Pryadeina,Burgart,Kodess,Saloutin
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p. 2841 - 2845
(2007/10/03)
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- Amides parahydroxycinnamiques: synthese et proprietes inhibitrices vis-a-vis de l'alcool coniferylique deshydrogenase (CADH)
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Parahydroxycinnamoyl amides are easily prepared from the lithioamines and the iminium salts of alkylated acids.Depending on the amine nucleophilic character, the yields are satisfactory with the aminopyridine derivatives, good for a natural product as the N-feruloyltryptamine 10.A good inactivation effect of the target enzyme CADH is observed with the aminopyridine derivatives, in particular with the N-feruloyl 2-amino pyridine 11.
- Duran, H.,Duran, E.,Bakkar, M. Ben,Gorrichon, L.,Grand, C.
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p. 672 - 680
(2007/10/02)
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