6966-55-8

Basic information

• Product Name: (2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one
• CAS NO: 6966-55-8
• Molecular Formula: C₉H₈N₂OS
• Molecular Weight: 192.2376
• Mol File: 6966-55-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 290.5°C at 760 mmHg
• Flash Point: 129.5°C
• Density: 1.37g/cm³
• Vapor Pressure: 0.00206mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: (2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one(6966-55-8)
• EPA Substance Registry System: (2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one(6966-55-8)

Safety Data

• Hazardous Substances Data: 6966-55-8(Hazardous Substances Data)

Usage

Description

(2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one is a chemical compound characterized by a thiazolidinone ring structure with a phenyl group attached to it. It is an imine derivative with a double bond configuration in the thiazolidinone ring. (2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one has been studied for its potential pharmaceutical applications, including antimicrobial, anti-inflammatory, and anticancer properties. It has also shown potential as an antitubercular agent. Furthermore, (2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one has been investigated for its potential use in organic synthesis and as a building block in the development of various bioactive compounds. Its structural features make it an interesting target for further research and development in the field of medicinal chemistry.

Uses

Used in Pharmaceutical Applications:
(2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one is used as a pharmaceutical agent for its antimicrobial, anti-inflammatory, and anticancer properties. Its potential as an antitubercular agent is also being explored.
Used in Organic Synthesis:
(2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one is used as a building block in the development of various bioactive compounds, contributing to the advancement of organic synthesis.
Used in Medicinal Chemistry Research:
(2Z)-2-imino-3-phenyl-1,3-thiazolidin-4-one is used as a target for further research and development in the field of medicinal chemistry due to its unique structural features and potential applications.

Upstream product

• 10156-35-1 thiocyanato-acetic acid anilide 
• 107-14-2 chloroacetonitrile 
• 705-62-4 N,N-dimethyl-N'-phenylthiourea 
• 333-20-0 potassium thioacyanate 
• 587-65-5 N-chloroacetyl-aniline 
• 151-50-8 potassium cyanide 
• 62-53-3 aniline 
• 79-11-8 chloroacetic acid 
• 103-85-5 monophenylthiourea 
• 103-72-0 phenyl isothiocyanate 

Downstream Products

• 17823-27-7 2-phenylaminothiazol-4-one 
• 52772-99-3 3-phenyl-2-(4-methyl-anilinomethylimino)-thiazolidin-4-one 
• 60708-68-1 (4-oxo-3-phenyl-thiazolidin-2-ylidene)-phenyl-thiourea 
• 52772-97-1 2-anilinomethylimino-3-phenyl-thiazolidin-4-one 
• 52773-02-1 2-(4-bromo-anilinomethylimino)-3-phenyl-thiazolidin-4-one 
• 102-15-8 phenylcarbamimidoylmercapto-acetic acid 
• 1010-53-3 3-phenyl-2,4-thiazolidinedione 
• 1228116-77-5 (Z)-5-(3-chloro-4-hydroxy-benzylidene)-2-imino-3-phenyl-thiazolidin-4-one 

Relevant articles and documents

Anti-hepatitis-C virus activity and QSAR study of certain thiazolidinone and thiazolotriazine derivatives as potential NS5B polymerase inhibitors

The present study reports on evaluation of anti-HCV activity and QSAR of certain arylidenethiazolidinone derivatives as potential inhibitors of HCV-NS5B polymerase. The pursued compounds involving, 5-aryliden-3-arylacetamidothiazolidin-2,4-diones 4–6(a–f), 5-arylidine-2-(N-arylacetamido)-iminothiazolidin-4-one (10) and their rigid counterparts 5-arylidinethiazolotriazines 13–15(a–f), were synthesized and their structures confirmed by spectral and elemental analyses. The results of NS5B polymerase inhibition assay revealed compound 4e, as the most active inhibitor (IC50 = 0.035 μM), which is four folds greater than that of the reference agent, VCH-759, (IC50 = 0.14 μM). Meanwhile, compounds 4b, 4c, 5a, and 5c, and 13b, 14e and 15c displayed equipotency to 2 folds higher activity than VCH-759 (IC50 values: 0.085, 0.14, 0.14, 0.10, 0.12, 0.09 and 0.07 μM, respectively). Assessment of the anti-HCV activity (GT1a) using human hepatoma cell line (Huh-7.5) illustrates superior activity of 4e (EC50 = 3.80 μM) relative to VCH-759 (EC50 = 5.29 μM). Cytotoxicity evaluation on, Transformed normal cell lines (Human Liver Epithelial-2, THLE-2 and Proximal Tubular Epithelial, RPTEC/TERT1), demonstrate enhanced safety profile of 4e (CC50 = 102.77, 161.37 μM, respectively) compared to VCH-759 (CC50 = 61.83, 81.28 μM, respectively). Molecular docking of the synthesized derivatives to NS5B polymerase allosteric site (PDB: 2HWH) showed similar binding modes to that of the co-crystallized ligand. Moreover, QSAR models were established for the studied thiazolidinones and thiazolotriazines to investigate the molecular characteristics contributing to the observed NS5B polymerase inhibition activity. The obtained results inspire further investigations of thiazolidinones and thiazolotriazine aiming at affording more potent, safe and orally active non-nucleoside NS5B polymerase inhibitors as anti-HCV drug candidates.

2-Imino-thiazolidin-4-one derivatives as potent, orally active S1P 1 receptor agonists

Sphingosine-1-phosphate (S1P) is a widespread lysophospholipid which displays a wealth of biological effects. Extracellular S1P conveys its activity through five specific G-protein coupled receptors numbered S1P1 through S1P5. Agonists of the S1P1 receptor block the egress of T-lymphocytes from thymus and lymphoid organs and hold promise for the oral treatment of autoimmune disorders. Here, we report on the discovery and detailed structure-activity relationships of a novel class of S1P1 receptor agonists based on the 2-imino-thiazolidin-4-one scaffold. Compound 8bo (ACT-128800) emerged from this series and is a potent, selective, and orally active S1P1 receptor agonist selected for clinical development. In the rat, maximal reduction of circulating lymphocytes was reached at a dose of 3 mg/kg. The duration of lymphocyte sequestration was dose dependent. At a dose of 100 mg/kg, the effect on lymphocyte counts was fully reversible within less than 36 h. Pharmacokinetic investigation of 8bo in beagle dogs suggests that the compound is suitable for once daily dosing in humans.

SYNTHESIS OF HETEROCYCLES VIA ENAMINES-X. REACTIONS OF 1-SUBSTITUTED-4,4,6-TRIMETHYL-1,4-DIHYDROPYRIMIDINE-2(3H)THIONE DERIVATIVES WITH α-HALOGENATED CARBOXYLIC ACIDS AND KETONES

2,4-dioxathiazolidine derivatives(7) have been obtained in synthetically useful yields by the condensations of easily available 1-substituted-4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H) thione derivatives (4) and α-halogenated carboxylic acids in aqueous