New thiazolidinedione-5-acetic acid amide derivatives: synthesis, characterization and investigation of antimicrobial and cytotoxic properties

Abstract

The present work describes the synthesis, antimicrobial and cytotoxic activity of 2,4-thiazolidinedione-5-acetic acid amides 3a-n. The structures of the compounds were confirmed by IR, 1 H, 13 C NMR and elemental analysis. All compounds were tested for antimicrobial activity by twofold serial dilution technique. The preliminary results revealed that the compound 3d exhibits promising antibacterial and antifungal activity. The cytotoxic (MTT) activity of 2,4-thiazolidinedione-5-acetic acid amides were tested in four tumour cell lines. We found that compound 3j inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with IC 50 values of 33, 35, 30 and 36 lM, respectively.

Synthesis and antifungal activity of thiadiazole-functionalized chitosan derivatives

“…2-Amino-1,3,4-thiadiazole and its derivatives (1) were prepared from substituted aryl acid and thiosemicarbazide in presence of dehydrating agent phosphorus oxychloride (POCl 3 ). 31 2.3.1. General procedure for synthesis of 2 32 2-Chloroacetyl chloride (24 mmol) was slowly added drop wise to a mixture of 1 (20 mmol) in anhydrous dioxane (20 mL) at 0°C.…”

Synthesis, Antimicrobial Activity and Structure-Activity Relationship of Some 5-Arylidene-thiazolidine-2,4-dione Derivatives

“…[3][4][5] In recent years, 5-arylidene-thiazolidine-2,4-dione derivatives have been emphasized in the field of synthetic organic chemistry. [1][2][3] Several synthetic protocols have been reported in the process of obtaining these derivatives. The 5-arylidene-thiazolidine-2,4-diones are preferentially obtained through Knoevenagel condensation of aromatic aldehydes with TZD, starting from the use of catalysts such as piperidine, nanoparticles of Zn, oxalic acid, LiBr, BiCl 3 , 3 NaOH, 4,5 tetrabutylammonium bromide (TBAB), sodium acetate and piperidine benzylate.…”

“…Also, they can present several substituents in positions 2, 3 and 5 ( Figure 1). 1,2 The first reaction in order to obtain TZD was described in an aqueous medium with cyclization, employing monochloroacetic acid and thiourea. 3 A variety of synthetic approaches have been reported involving this core, which presents several reactive sites that promote substitutions in the heterocyclic ring.…”

Synthesis and in vitro antiproliferative and antibacterial activity of new thiazolidine-2,4-dione derivatives

“…A number of derivatives of 2,4-dioxothiazolidine-5-acetic acid with the ring of 5-substituted-2-amino-1,3,4-thiadiazole showed cytotoxic effects in vitro against four human tumour cell lines (cervical carcinoma – HeLa, colorectal cancer – HT29, lung cancer – A549, and breast cancer – MCF-7). Among the 14 derivatives, 2-(2,4-dioxo-1,3-thiazolidin-5-yl)-N-[5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazol-2-yl]acetamide showed significant inhibitory activity against the tested cell lines 6 .…”

“…Thiazolidine-2,4-diones are known as antidiabetic drugs and include rosiglitazone, pioglitazone, and darglitazone. Moreover, thiazolidine-2,4-dione derivatives possess biological activities such as aldose reductase inhibitory 9 , antibacterial 6 , 10–13 , antifungal 10 , antitubercular 14 , and anti-inflammatory activity 15 , etc.…”