Abstract:
Chiral protected and deprotected amides were synthesized by using commercially
available L-tartaric acid having two asymmetric centers and C2 axis of symmetry. In
the synthetic sequence, diacid functionality of L-tartaric acid was protected as
dimethyl ester and diol as 1,3-dioxolane. The partial hydrolysis of 1,3-dioxolane
dimethyl ester gave the corresponding monoester. Monoester upon treatment with
different substituted anilines gave desired amides (2a-2t). Amides (2a-2t) afforded
compounds (3a-3t) with the aid of acetyl chloride in methanol. All the compounds
were characterized by using sophisticated spectroscopic techniques including IR, 1H
NMR, 13C NMR, EI-MS and elemental analysis. The structures of compounds 2g, 2r
and 3i were also unambiguously confirmed by X-ray crystallography.
Protected (2a-2l) and deprotected amides (3a-3l) were tested for their antimicrobial
activities at different concentrations against different fungal and bacterial strains and
were found effective. Monoaryl esters of L-tartaric acid (4a-4h) were prepared and
processed further in Fries rearrangement. The structure of compound 4e in the series
was also confirmed by X-ray crystallography.
N-Linked glycopyranosides (10a-10e) and O-Linked glycopyranosides (11a-11e)
were synthesized from monoester of L-tartaric acid. The synthesized compounds were
confirmed with the aid of spectroscopic techniques. The structure of compound 11c in
the series was supported by X-ray analysis. Antileishmanial activity of the
glycopyranosyl amides (10a-10e) and glycopyranosides (11a-11e) was assayed which
showed moderate to good activities. Synthesis of glycoconjugates (13a-13e) was
carried out by using glycopyranosyl α-trichloroacetimidates and dimethyl-L-tartrate.
Chiral imides and amides were prepared from diacetyl-L-tartaric acid anhydride and
aliphatic, substituted aromatic amines and amino acids. The imides (14g-14m) were
subjected for their antifungal and antibacterial activities against different fungal and
bacterial strains. All the compounds showed good antifungal and moderate to good
antibacterial activities.
