Herein, we describe a new strategy for the preparation of thiazolothiazepine-based inhibitors of human immunodeficiency virus type-1 integrase (IN). The present method allows facile preparation of the title compounds in a single enantiomeric form starting from l-4-thiazolidinecarboxylic acid. This method could be easily extended to the synthesis of several analogs derived from optically active cyclic aminoacids. We also present a putative model showing the interaction between l- and d-isomers of compound 1 in the IN active site. A sensibly lower IC(50) value was found for (-)-1 over racemic-1 in an anti-IN assay.

F., A., Brizzi, A., O., D.G., A., G., F., G., M. S., S., et al. (2006). An approach to the stereo-controlled synthesis of polycyclic derivatives of L-4-thiazolidinecarboxilic acid active against HIV-1 integrase. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 41, 914-917 [10.1016/j.ejmech.2006.03.032].

An approach to the stereo-controlled synthesis of polycyclic derivatives of L-4-thiazolidinecarboxilic acid active against HIV-1 integrase

BRIZZI, ANTONELLA;
2006

Abstract

Herein, we describe a new strategy for the preparation of thiazolothiazepine-based inhibitors of human immunodeficiency virus type-1 integrase (IN). The present method allows facile preparation of the title compounds in a single enantiomeric form starting from l-4-thiazolidinecarboxylic acid. This method could be easily extended to the synthesis of several analogs derived from optically active cyclic aminoacids. We also present a putative model showing the interaction between l- and d-isomers of compound 1 in the IN active site. A sensibly lower IC(50) value was found for (-)-1 over racemic-1 in an anti-IN assay.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11365/24131
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