23969-11-1Relevant academic research and scientific papers
Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-D-hexosaminidase and chitinase
Yang, Huibin,Qi, Huitang,Hao, Zesheng,Shao, Xusheng,Liu, Tian,Yang, Qing,Qian, Xuhong
, p. 1271 - 1275 (2019/12/24)
Insect chitinase and N-acetyl-β-D-hexosaminidases (Hex) are potential targets for developing new pesticides. Here, a series of thiazolylhydrazones I (with substituted group R1 at N3) and II (with substituted group R1 at N2) were designed, synthesised and evaluated as competitive inhibitors of OfHex1 and OfChi-h, from the agricultural pest Ostrinia furnacalis. Derivatives I-3d and II-3d, with phenoxyethyl group at R1, demonstrated the best inhibitory activities against OfHex1 and OfChi-h. Molecular docking analysis indicated that the branched conformation compound II-3d (Ki = 1.5 μmol/L) formed more hydrogen bonds with OfHex1 than the stretched conformation compound I-3d (Ki = 5.9 μmol/L). The differences in compounds’ binding conformations with OfChi-h explained differences in inhibitory activity of compounds I-3d (Ki = 1.9 μmol/L) and II-3d (Ki = 4.1 μmol/L). This work suggests a novel scaffold for developing specific Hex and Chi-h inhibitors.
Synthesis, biological evaluation and quantitative structure-active relationships of 1,3-thiazolidin-4-one derivatives. A promising chemical scaffold endowed with high antifungal potency and low cytotoxicity
Carradori, Simone,Bizzarri, Bruna,D'Ascenzio, Melissa,De Monte, Celeste,Grande, Rossella,Rivanera, Daniela,Zicari, Alessanda,Mari, Emanuela,Sabatino, Manuela,Patsilinakos, Alexandros,Ragno, Rino,Secci, Daniela
, p. 274 - 292 (2017/10/05)
With reference to recent studies reporting on the various biological properties of the thiazolidinone scaffold, we synthesized more than a hundred compounds characterized by a 1,3-thiazolidin-4-one nucleus derivatised at the C2 with a hydrazine bridge linked to (cyclo)aliphatic or hetero(aryl) moieties, and their N-benzylated derivatives. These molecules were assayed as potential anti-Candida agents and they were shown to possess comparable, and in some cases higher biological activity than well-established topical and systemic antimycotic drugs (i.e. clotrimazole, fluconazole, ketoconazole, miconazole, tioconazole, amphotericin B). Compounds endowed with the lowest MICs underwent further testing in order to assess their cytotoxic effect (CC50) on Hep2 cells, which demonstrated their relative safety. Finally, QSAR and 3-D QSAR models were used to predict putative chemical modifications of the 1,3-thiazolidin-4-one scaffold in order to design new and potential more active compounds against Candida spp.
An environmentally benign one pot synthesis of pyrazole substituted-2-hydrazolyl-4-Thiazolidinones
Bhosle, Manisha R.,Khillare, Lalit D.,Dhumal, Sambhaji T.,Mane, Ramrao A.
, p. 148 - 155 (2016/03/01)
Background: Thiazolidinone and pyrazoles are promising heterocyclic systems enormously contributing to medicinal chemistry and when pyrazole nucleus was incorporated in other biodynamic heterocycles, the resulting molecules have displayed an increased spectrum of biological activities. There are several synthetic routes for the synthesis of thiazolidinone molecules but are having certain lacunas like, need of catalysts and desiccants, higher reaction temperature, longer reaction time, organic solvents and tedious work up procedure. Methods: Here an ultrasound promoted one pot multicomponent protocol is developed for 2-[(1-phenyl-3-(substituted phenyl)-pyrazol-4-yl)] methylene hydrazolyl-4-Thiazolidinones (6a-g). Here freshly prepared substrates, 3-(4-substituted phenyl)-1-phenyl-1H-pyrazole-4-carbaldehydes (5a-g), have been condensed with thiosemicarbazide (2) and ethylbromo acetate (3) in aqueous emulsion of surfactant, CTAB under ultrasonication. Results: In our study the titled compounds 2-[(1-phenyl-3-(substituted phenyl)-pyrazol-4-yl)] methylene hydrazolyl-4-thiazolidinones obtained with good to excellent yields using 20 mol% aqueous emulsion of CTAB under ultrasound irradiation at 60°C. Conclusion: First time we have provided an environmentally friendly ultrasound promoted synthetic route to 2-hydrazolyl-4-Thiazolidinones (4a-g) and biologically significant 2-[(1-phenyl-3-(substituted phenyl)-pyrazol-4-yl)] methylene hydrazolyl-4-Thiazolidinones (6a-g) using aqueous emulsion of CTAB as reaction medium. The method offered several advantages such as operational simplicity, easy work-up procedure, shorter reaction times and high yields. The protocol is safe, economic and convenient for obtaining library of 2-hydrazolyl/imino-4-Thiazolidinones rapidly.
Synthesis and Structure of Some Thiazole Derivatives
Badawy, Mohammed A.,Abdel-Hady, Sayed A.,Ibrahim, Yehia A.
, p. 393 - 395 (2007/10/02)
The addition of thiosemicarbazones 1 to α-halo acids 2 is shown to give 2-hydrazino-2-thiazolin-4-ones 3 and not 3-substituted 2-imino-3-(methyleneimino)thiazolidin-4-ones 4.The independent synthesis of 2-thiazolin-4-one derivatives 3 is also described.
