Synthesis, characterization, antimicrobial and antileishmanial activities of amide derivatives of L-tartaric acid

Sixteen (16) chiral, amides were synthesized from commercially available L-tartaric acid, having two asymmetric centers and C2 axis of symmetry. The diacid functionality of L-tartaric acid was protected as dimethyl ester and dihydroxy groups as acetonoid. The partial hydrolysis of acetonoid of dimethyl ester gave the corresponding monoester. Monoester upon treatment with different substituted aromatic amines gave desired amides (1-8). Amides (1-8) afforded deprotected compounds (9-16) after reacting with acetyl chloride and methanol. All the compounds were characterized by using spectroscopic techniques such as IR, 1H-NMR, 13C-NMR, and EIMS. The compounds gave reasonable elemental analyses. The structure of compound 6 was unambiguously obtained by X-ray crystallography. Protected (1-8) and deprotected amides (9-16) were tested for their antileishmanial (against Leshmania tropica KWH23 Promastigotes) and antimicrobial activities at different concentrations against different strains of bacteria and fungi.