Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazono]-4-oxo-3-phenyl-5-thiazolidineacetic acids

Synthesis of Novel Highly Functionalized 4-Thiazolidinone Derivatives from 4-Phenyl-3-thiosemicarbazones

“…Thiosemicarbazones are a class of small molecules that have been evaluated over the last 50 years as antiviral [1] and as antitumoral agents [2][3][4], in addition to their antiparasitic and bacterial action against Trypanasoma cruzi [5][6][7] and Toxoplasma gondii and several bacterial strains [8]. Thiosemicarbazones have been used as intermediates for a great variety of heterocyclic products, such OPEN ACCESS as thiazolidinones, thiohydantoins, thioxopyrimidinediones.…”

Indole-based hydrazide-hydrazones and 4-thiazolidinones: synthesis and evaluation as antitubercular and anticancer agents

“…All the newly synthesized compounds (6)(7)(8) were evaluated for in vitro anti-TB activity against M. tuberculosis H37Rv. The 4-thiazolidinone derivatives 7g-7j, 8g, 8h and 8j displayed appreciable anti-TB activity showing 99% inhibition at MIC values ranging from 25.0 to 6.25 mg/ml along with rather low cytotoxicity against mammalian cell lines.…”

“…Studies on the identification of the molecular target for indole-2-carboxamides suggest that they may inhibit M. tuberculosis growth by acting on the MmpL3 protein, which belongs to the family of membrane transporters 22 . Several studies have been devoted to the antiproliferative activity of hydrazide-hydrazone (-CO-NH-N¼CH-) based compounds that have structural similarity to our target indolylhydrazones (6). In an early report, Germain et al identified a series of acyl hydrazones to be selectively lethal to breast cancer stem cell enriched populations 23 .…”

“…An early representative actithiazic acid, (À)-2-(5-carboxypentyl)thiazolidin-4-one (Figure 1), isolated from the culture broth of a strain of streptomyces shows highly specific in vitro activity against MTB 4,5 . 2-Arylhydrazono-4-oxo-3-phenyl-5-thiazolidinone acetic acids 6 , piperidone based 1,3-thiazolidin-4-ones 7 , isonicotinyl hydrazide derivatives containing the 4-thiazolidinone nucleus 8 and numerous different 2,3-disubstituted or 2,3,5-trisubstituted 4-thiazolidinones [9][10][11] have been reported to possess appreciable in vitro antitubercular activity. Likewise, spirothiazolidinone featured molecules, N-alkyl substituted spirothiazolidinones 13 , spirothiazolidinones bearing the imidazo [2,1-b]thiazole residue 14 and indole-2-carboxamides with a spirothiazolidinone moiety 15 , have been found to be effective as growth inhibitors of MTB.…”

Synthesis, structures, and property studies on Zn(II), Ni(II), and Cu(II) complexes with a Schiff base ligand containing thiocarbamide group

“…Herein, we wish to report another Schiff base ligand of 4-phenyl-1-(4-methoxyl-1-phenylethylidene)thiosemicarbazide (HL) and its chelate complexes of ZnL 2 (1), NiL 2 (2), and CuL 2 (3), including their crystal structures, UV-Vis spectra, fluorescence spectra, thermal stabilities, and electrochemical behaviors. To the best of our knowledge, although the synthesis of HL [17,18] and the crystal structure of its Pd complex [19] have been reported earlier, the crystal structures and the properties of HL and 1, 2, and 3 have not been found till now. Additionally, in this article, density functional theory (DFT) calculations are performed to help to explain the electronic spectra.…”