Synthesis and Evaluation of Cytotoxic Activity on Mcf-7 Cell Line of Some Diesters Derived from 5-(Hydroxybenzylidene)Thiazolidine-2,4-Diones

Abstract

Knoevenagel condensation of thiazolidine-2,4-dione, which were prepared from chloroacetic acid and thioure by 1,3 dipolar cycloaddition reaction, with 2-hydroxybenzaldehyde, 5-bromo-2-hydroxybenzaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde and 4-hydoxy-3-methoxybezaldehyde gave five corresponding 5-(hydroxybenzylidene)thiazolidine-2,4-dione compounds. The reaction of 5-(hydroxybenzylidene)thiazolidine-2,4-diones and ethyl chlorofomate or ethyl chloroacetate occurred at both NH and OH centers and gave ten corresponding diesters. The structures of the diesters were confirmed by IR, MS, 1H and 13C-NMR spectral data. However, in test for cytotoxic activity against MCF-7 cells, none of the diester compounds exhibited significant activity.

Antifungal Thiazolidines: Synthesis and Biological Evaluation of Mycosidine Congeners

“…The interactions of chloroformates with TZD derivatives containing hydroxyl groups in the arylidene fragment have recently been described in the literature [ 50 , 51 ]. The reactions were carried out in dry acetone in the presence of potassium carbonate.…”

“…The reactions were carried out in dry acetone in the presence of potassium carbonate. With an equimolecular ratio of reagents, the substitution on only the phenolic hydroxyl group is described [ 50 ], and with the double equivalent of the chloroformate and potassium carbonate, two reaction centers were involved at once with substitution at the ring nitrogen atom and the hydroxyl group of the arylidene radical [ 51 ]. The only N -ethoxycarbonyl derivative, obtained from the potassium salt of 5-nitrofurfurilidene-thiazolidine-2,4-dione with ethyl chloroformate in DMF, was described in a French patent [ 52 ].…”