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-thiazolidinecarboxylicacid. This method could be easily extended to the synthesis of several analogs derived from optically active cyclic aminoacids. We alsopresent a putative model showing the interaction between L- and D-isomers of compound 1 in the IN active site. A sensibly lower IC50 value wasfound for (–)-1 over racemic-1 in an anti-IN assay.

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

Aiello, Francesca;De Grazia, O;Garofalo, Antonio
;
Grande, Fedora;Sinicropi, Maria Stefania;
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-thiazolidinecarboxylicacid. This method could be easily extended to the synthesis of several analogs derived from optically active cyclic aminoacids. We alsopresent a putative model showing the interaction between L- and D-isomers of compound 1 in the IN active site. A sensibly lower IC50 value wasfound for (–)-1 over racemic-1 in an anti-IN assay.
HIV-1 integrase inhibitors, L-4-thiazolidinecarboxylic acid, Thiazolothiazepines
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/20.500.11770/141057
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