Preparations of 5-alkylmethylidene-3-carboxymethylrhodanine derivatives and their aldose reductase inhibitory activity.

Abstract

Reactions of 3-carboxymethylrhodanine (1) with aldehydes (2a-u) afforded stereoselectively the 5-mono-alkylmethylidene-3-carboxymethylrhodanines (3a-u). The configuration of the 5-monoalkylmethylidene-3-carboxymethylrhodanine (3k) were examined by X-ray structure analysis and confirmed to be Z-configuration. The stereoselective reaction path was discussed. Several 5-dialkylmethylidene-3-carboxymethylrhodanines (15a-f) and alkylamino derivatives of 3-carboxymethylrhodanines (18a-o) were also prepared. These products were evaluated for aldose reductase-inhibitory potency and half of them exhibited valuable inhibitory potency.

Design, synthesis and biological evaluation of novel 4-thiazolidinones containing indolin-2-one moiety as potential antitumor agent

“…The exclusive formation of the thermodynamically stable Z-isomers is in agreement with which was reported for similar structures in literature [24,25]. This downfield movement of methine proton in 3ae3h and 8ae8f was due to the deshielding effect of the adjacent carbonyl group at the 4-position.…”

Synthesis and Anticancer Activity of Indolin‐2‐one Derivatives Bearing the 4‐Thiazolidinone Moiety

“…The presence of only one signal for the methyne proton at more downfield 7.83-7.95 ppm in 1 H-NMR spectra of 2a-2f suggested that a single Z-configuration isomer was present. The exclusive formation of the thermodynamically stable Z-isomers of 2a-2f is in agreement with the literature reports for similar compounds [21,22]. S-Ethylation of 2a-2f with boron trifluoride diethyl etherate and triethyl orthoformate produced thiazolinium salts 3a-3f, which reacted with indolin-2-ones 4a-4e in the presence of triethylamine to yield compounds 5a-5p.…”

Structure-based virtual screening, synthesis and SAR of novel inhibitors of hepatitis C virus NS5B polymerase

“…Addition of arylalkylidene moiety at C 5 -position of the rhodanine-3-acetic acid was accomplished by a Knoevenagel condensation to afford target compounds 23-28 as shown in Scheme 1. This condensation reaction with aromatic aldehyde provided only the Z isomer, as determined by the chemical shift of the methylene proton ranging from 7.9-8.1 as a singlet 45,46. The synthesized compounds 23-28 were subjected to in vitro NS5B evaluation (Table 2).…”