Synthesis and Characterization of Some New Thiazolidinones for Potential Applications in Medicinal Chemistry

Abstract

Thiazolidin-4-one serves as an intriguing and privileged scaffold in medicinal chemistry due to its ability to interact with various biological targets. Several thiazolidin-4-ones analogues were investigated to be the more effective than standard drugs because this small heterocycle has the potential to exhibit a plethora of pharmacological and biological activities including anticancer, anti-inflammatory, anti HIV, antitubercular, anticonvulsant and antioxidant. In this dissertation, a synthetic strategy has been designed for bis(thiazolidin-4-ones) (2Cl-2c15) by considering the expanding field of bisheterocycles. 5-Arylidine variants (2dl-2d4) of bis(thiazolidin-4-ones) (2CI-2cI5) have been synthesized with two equivalents of differently substituted benzaldehydes undergoing Knoevenagel condensation. Several Schiff bases (2bl-2bI5) were synthesized as intermediate by the condensation reaction of 4-(2-(4-formyl phenoxy) ethoxy)benzaldehyde (2a) with two equivalents of various anilines followed by the reaction of Schiff bases (2bl-2b15) with an excess ofthioglycolic acid moiety enduring the cyclocondensation process for the preparation of series of novel bis(thiazolidin-4- ones) (2Cl-2c15). Moreover, two equivalents of 4-hydroxybenzaldehyde were utilized to can)' out nucleophilic substitution reactions at both carbons of 1,2-dibromoethane, in order to synthesize compound (2a) as a precursor. Thin layer chromatography (TLC) and melting point determination facilitated to differentiate the synthesized compounds during and after the reaction completion. The structures of all synthesized compounds were further characterized by spectroscopic techniques including FTIR, 1 HNMR, and 13CNMR. All the synthesized compounds ought to have the cytotoxic potential to become future drug leads and, hence will be evaluated for anticancer as well as other biological activities.