Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Abstract

In past decades, interdisciplinary research has been of great interest for scholars. Thiazolidine motifs behave as a bridge between organic synthesis and medicinal chemistry and compel researchers to explore new drug candidates. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. The presence of sulfur enhances their pharmacological properties, and, therefore, they are used as vehicles in the synthesis of valuable organic combinations. They show varied biological properties viz. anticancer, anticonvulsant, antimicrobial, anti-inflammatory, neuroprotective, antioxidant activity and so on. This diversity in the biological response makes it a highly prized moiety. Based on literature studies, various synthetic approaches like multicomponent reaction, click reaction, nano-catalysis and green chemistry have been employed to improve their selectivity, purity, product yield and pharmacokinetic activity. In this review article, we have summarized systematic approaches for the synthesis of thiazolidine and its derivatives, along with their pharmacological activity, including advantages of green synthesis, atom economy, cleaner reaction profile and catalyst recovery which will help scientists to probe and stimulate the study of these scaffolds.

2-Mercaptomethyl-thiazolidines use conserved aromatic–S interactions to achieve broad-range inhibition of metallo-β-lactamases

“…Thiazolidines are versatile motifs broadly used in medicinal chemistry 33 that can be easily obtained by the condensation between carbonyls and 1,2-aminothiols. Based on the required structural features, two series of 2-ethoxycarbonyl-2-mercaptomethyl thiazolidine-4-carboxylic acids were designed ( Fig.…”

“…Since a TZ containing two carboxylate groups was shown to be a potent inhibitor of the B1 enzyme CcrA (Figure 1), 32 we hypothesized that a MMTZ molecule would elicit even more potent inhibition due to the presence of the zinc-binding thiol moiety. Thiazolidines are versatile motifs broadly used in medicinal chemistry 33 that can be easily obtained by the condensation between carbonyls and 1,2-aminothiols. Based on the required structural features, two series of 2-ethoxycarbonyl-2mercaptomethyl thiazolidine-4-carboxylic acids were designed (Figure 2), 1a with R = H, and 1b with R = Me, thus including the gem dimethyl group present in penicillins.…”

Acridine‐1,8‐diones: Synthesis and Biological Applications

“…Owning to this, a detailed discussion is a demand of present era to demonstrate the huge expansion and state-of-art innovation on this field. Motivated by the aforesaid outcomes and in continuation of our interest in the N-heterocyclic scaffolds studies, [33][34][35][36][37] a comprehensive and systematic review article on acridine-1,8-dione's synthetic pathways and bio-applicability from 1980's to date has been written by our research group which divulges their utility as a potent pharmacophore for the treatment of different ailments and also enlighten their current propersity in diverse areas. Firstly, we have recapitulated synthetic methodologies of acridinediones via varied routes like use of different catalysts, acid, metal, nano-catalyst, ionic-liquid, deep eutectic solvent applying conventional heating, stirring, microwave-irradiation (MWI), ultrasound (US) and other energy sources.…”

Metal Free Sulfonic Acid Functionalized Carbon Catalyst for Green and Mechanochemical Synthesis of Perimidines

“…Hence, for sustainable and green synthesis, there is a prerequisite need for efficient catalysis under mild conditions. As a part of our interest and continuation of our research in heterocyclic synthesis [32][33][34][35] , we concerned to develop a green catalytic pathway to prepare nitrogen containing heterocycles. Special characteristics of C-SO 3 H and our previous success [36,37] motivated and inspired us to use them as a better catalyst in the designing of perimidine molecules in terms of eco-friendliness, and sustainability.…”