The condensation of L‐cysteine with enantiomerically pure aldehyde 2a and 2b afforded a mixture of 2‐substituted thiazolidine diastereomers 1a‐b and 1c‐d, respectively. The present paper deals with the use of nuclear Overhauser effect (nOe) in determining the absolute configurations of the stereocenters.

A series of anti-HIV prodrugs possessing various polyaminated side arms have been developed. The incorporation of a N-Boc protected monoamine or diamine side arm into the backbone of the 2',3'-dideoxy-3'-thiacytidine 1 (BCH-189) provided an increase in antiviral potency, which could be several orders magnitude greater than the parent drug (1) depending on the cell culture systems used (MT-4 or MDMs). Twenty six 2',3'-dideoxy-3'-thiacytidine prodrugs which differ from each other by the length, the nature of the 5'-O function and the 5'-O or/and N-4 position on the nucleoside moiety were synthesized. Among this new series of prodrugs, several congeners (12c and 12a) were found to inhibit HIV-1 replication in cell culture with 50% effective concentrations EC50 of 10 and 50 nM respectively, in MT-4 cells. Compound 12c was found more active on infected MDMs cells with 50% effective concentration of 0.01 nM. The synthesis and the antiviral properties of these compounds are discussed.

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A number of 2‐substituted‐4‐thiazolidinecarboxylic acid derivatives were synthesized by cyclocondensation of L‐cysteine or its esters with various aldehydes, resulting from acids provided with antiinflammatory properties. In the cyclocondensation a new chiral center at C‐2 position of thiazolidine ring is formed giving rise to a mixture of diastereoisomers which can be partially separated. These diastereoisomers show in solution a fast epimerisation at the same chiral center as evidenced by 1H‐nmr studies.

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