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;
2006-01-01

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.
2006
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].
File in questo prodotto:
File Dimensione Formato  
Lavoro Eur. J. Med. Chem. 2006.pdf

non disponibili

Tipologia: Post-print
Licenza: NON PUBBLICO - Accesso privato/ristretto
Dimensione 288.08 kB
Formato Adobe PDF
288.08 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/24131
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo