The separated enantiomers of 2'-deoxy-3'-thiacytidine (BCH 189) both inhibit human immunodeficiency virus replication in vitro

Abstract

Racemic 2'-deoxy-3'-thiacytidine (BCH 189) is a dideoxycytidine analog having a sulfur atom in place of the 3' carbon. The enantiomers of BCH 189 have been resolved and found to be equipotent in antiviral activity against human immunodeficiency virus types 1 and 2. However, the (-)-enantiomer (3TC) is considerably less cytotoxic than the (+)-enantiomer.

The Effect of Absolute Configuration on the Anti-HIV and Anti-HBV Activity of Nucleoside Analogues

“…Two analogues of cytosine, cis-1-[2-(hydroxymethyl)-1 ,3-oxathiolane-5-yl]cytosine (BCH 189; Fig. 1b) and cis-e-fluoro-t-[2-(hydroxymethyl)-1,3-oxathiolane-5-yl]cytosine (FTC; Fig.1c), have extremely potent activity against both HIV-1 and HBV (Doong et el., 1991;Coats et al, 1992a;Coats et et., 1992b;Furman et al, 1992;Schinazi et al, 1992) (Table 1). However, BCH…”

Toward supramolecular architectures of the anti-HIV drug lamivudine: understanding the effect of the inclusion of water in a hydrochloride form

“…5,6 Furthermore, the engineering, prediction and understanding of salt formation are based on elegant chemical approaches on assembly mechanisms driven by molecular recognition events, which contribute to an easier legal process for protection of intellectual property on novel API crystal phases due to nonobviousness of designed molecular salts. Lamivudine (b-L-2 0 ,3 0 -dideoxy-3 0 -thiacytidine, 3TC) belongs to the class of nucleoside reverse transcriptase inhibitors (NRTIs), and it is being used worldwide in anti-HIV therapy 8 and also against hepatitis B virus.…”

Synthesis of 4′-Thionucleosides as Antitumor and Antiviral Agents

“…39) Indeed, the L-isomer of lamivudine was more potent and less cytotoxic than its D-isomer. [40][41][42][43] We concluded that our synthetic approach was effective. Adopting a similar synthetic scheme for the D-isomers depicted above, we were able to obtain L-4′-thioarabinonucleosides from D-xylose by shifting the chiral carbons employed.…”