Synthesis of Some New Thiazolidine Derivatives and Their Biological Significance

Abstract

An efficient route for the synthesis of new series of N-[3-(1H-1,2,3benzotriazol-1-yl)-propyl]-2-(substituted phenyl)-4-oxo-5-(substituted benzylidene)-1,3-thiazolidine carboxamide, compounds 5 (a-j) has been elaborated. The compounds 5 (a-j) have been synthesized and characterized by IR, 1 H NMR, 13 C NMR, FAB Mass spectra and chemical analysis. All final compounds were screened for their antimicrobial activity against some selected bacteria, fungi, antituberculosis (against M. tuberculosis) and antiinflammatory activity on albino rats.

The Synthesis and the Biological Evaluation of New Thiazolidin-4-one Derivatives Containing a Xanthine Moiety

“…For these compounds the EC 50 values were 0.033 ± 0.0019 (for 7a 5 ) and 0.033 ± 0.0012 (for 7a 6 ), which means that they are about four times more active than the corresponding thiazolidin-4-one (6a, EC 50 = 0.137 ± 0.0036). Regarding the compounds 7b 1-7 obtained through condensation of 3-(4-chlorophenyl)-thiazolidin-4-one derivative 6b with several aromatic benzaldehydes, we could observe that the most active compounds were 7b 5 and 7b 6 , the corresponding analogues of 7a 5 and 7a 6 . These compounds were about 5.7 times (7b 5 , EC 50 = 0.027 ± 0.0013) and 6.7 times (7b 6 , EC 50 = 0.023 ± 0.0011) more active than the corresponding thiazolidin-4-one derivative (6b, EC 50 = 0.155 ± 0.0038).…”

“…Synthetic procedure for compounds 7a 1-7 , 7b [1][2][3][4][5][6][7] . Reagents and conditions: (a) sodium, absolute methanol; (b) ethyl chloroacetate, ethanol:DMFA, heating 7 h; (c) hydrazine hydrate, ethanol, heating 6 h; (d) phenyl isothiocyanate/4-chlorophenyl isothiocyanate, 1,4-dioxane:DMFA, heating 6 h; (e) chloroacetyl chloride, methanol:chloroform, heating 10 h; (f) aromatic aldehydes, 1,4-dioxane, piperidine, heating 6 h.…”

“…It was also observed that both series of compounds 7a 1-7 , 7b 1-7 have a comparable reducing power. In the series of 3-phenylthiazolidin-4-one derivatives 7a 1-7 the most active compounds were those which resulted from condensation with 4-hydroxybenzaldehyde (compound 7a 5 ) and 4-dimethlaminobenzaldehyde (compound 7a 6 ). For these compounds the EC 50 values were 0.033 ± 0.0019 (for 7a 5 ) and 0.033 ± 0.0012 (for 7a 6 ), which means that they are about four times more active than the corresponding thiazolidin-4-one (6a, EC 50 = 0.137 ± 0.0036).…”

“…In the series of 3-phenylthiazolidin-4-one derivatives 7a 1-7 the most active compounds were those which resulted from condensation with 4-hydroxybenzaldehyde (compound 7a 5 ) and 4-dimethlaminobenzaldehyde (compound 7a 6 ). For these compounds the EC 50 values were 0.033 ± 0.0019 (for 7a 5 ) and 0.033 ± 0.0012 (for 7a 6 ), which means that they are about four times more active than the corresponding thiazolidin-4-one (6a, EC 50 = 0.137 ± 0.0036). Regarding the compounds 7b 1-7 obtained through condensation of 3-(4-chlorophenyl)-thiazolidin-4-one derivative 6b with several aromatic benzaldehydes, we could observe that the most active compounds were 7b 5 and 7b 6 , the corresponding analogues of 7a 5 and 7a 6 .…”

“…A survey of the literature reveals that extensive studies have been carried out on the synthesis of thiazolidines. These compounds are known to exhibit interesting biological activity such as antimicrobial [2][3][4][5], antitubercular [6], antipsihotic [7], anticancer [8,9], antiviral [10], anti-HIV [11], anti-inflammatory [12,13] and antihyperglycemic [14][15][16][17] effects. As antidiabetic drugs, thiazolidinediones (pioglitazone-Actos ® and rosiglitazone-Avandia ® , Figure 1) have an important place in type 2 diabetes mellitus therapy [18].…”