115163-95-6

Basic information

• Product Name: 2-((E)-2-[(E)-1-PHENYLETHYLIDENE]HYDRAZONO)-1,3-THIAZOLAN-4-ONE
• Synonyms: 2-((E)-2-[(E)-1-PHENYLETHYLIDENE]HYDRAZONO)-1,3-THIAZOLAN-4-ONE
• CAS NO: 115163-95-6
• Molecular Formula: C₁₁H₁₁N₃OS
• Molecular Weight: 233.29
• Mol File: 115163-95-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-((E)-2-[(E)-1-PHENYLETHYLIDENE]HYDRAZONO)-1,3-THIAZOLAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((E)-2-[(E)-1-PHENYLETHYLIDENE]HYDRAZONO)-1,3-THIAZOLAN-4-ONE(115163-95-6)
• EPA Substance Registry System: 2-((E)-2-[(E)-1-PHENYLETHYLIDENE]HYDRAZONO)-1,3-THIAZOLAN-4-ONE(115163-95-6)

Safety Data

• Hazardous Substances Data: 115163-95-6(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 2302-93-4 acetophenonethiosemicarbazone 
• 105-36-2 ethyl bromoacetate 
• 79-11-8 chloroacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 42345-82-4 (E)-1,2-dichloro-1-ethoxy-ethene 

Downstream Products

• 1623025-78-4 3-benzyl-2-(2-(1-phenylethylidene)hydrazono)thiazolidin-4-one 
• 93691-32-8 (E)-2-((E)-(2-nitrobenzylidene)hydrazono)thiazolidin-4-one 

Relevant articles and documents

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

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.

Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii

We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition.