81154-12-3

Basic information

• Product Name: (5Z)-5-(2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
• Synonyms: (5Z)-5-(2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one
• CAS NO: 81154-12-3
• Molecular Weight: 237.303
• Mol File: 81154-12-3.mol

Chemical Properties

• CAS DataBase Reference: (5Z)-5-(2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z)-5-(2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one(81154-12-3)
• EPA Substance Registry System: (5Z)-5-(2-hydroxybenzylidene)-2-thioxo-1,3-thiazolidin-4-one(81154-12-3)

Safety Data

• Hazardous Substances Data: 81154-12-3(Hazardous Substances Data)

Upstream product

• 141-84-4 2-thioxo-4-thiazolidinone 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 6968-92-9 2-(2-hydroxybenzylidene)malononitrile 

Downstream Products

• 102595-23-3 5-salicylidene-2-thioxo-3-xanthen-9-yl-thiazolidin-4-one 
• 145903-73-7 piperidine salt of (E,Z)-5-(2-hydroxyphenylmethylene)-4-oxo-2-thioxothiazolidine 
• 101444-73-9 5-(2-hydroxyphenylmethylene)-2-benzylimino-4-oxothiazolidine 
• 81182-99-2 5-(2-hydroxyphenylmethylene)-2-piperidino-4-oxo-2-thiazoline 
• 81154-06-5 E-5-(2-hydroxyphenylmethylene)-2-morpholino-4-oxo-2-thiazoline 
• 345932-21-0 5-(2-hydroxyphenylmethylene)-2-(4-methylphenylimino)-4-oxothiazolidine 
• 1181081-62-8 (5Z)-5-[(2-hydroxyphenyl)methylidene]-2-(4-phenylpiperazin-1-yl)-4,5-dihydro-1,3-thiazol-4-one 
• 1181081-65-1 (5Z)-2-(azetidin-1-yl)-5-[(2-hydroxyphenyl)methylidene]-4,5-dihydro-1,3-thiazol-4-one 
• 1081758-09-9 C₉H₈O₃S 
• 1353992-44-5 4-(4-chlorophenyl)-2-(2-hydroxybenzylidene)-1-thia-4-aza-spiro[4.5]decan-3-one 

Relevant articles and documents

Environmentally friendly approach to knoevenagel condensation of rhodanine in choline chloride: Urea deep eutectic solvent and qsar studies on their antioxidant activity

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Molecular modeling of drug-pathophysiological Mtb protein targets: Synthesis of some 2-thioxo-1, 3-thiazolidin-4-one derivatives as anti-tubercular agents

Twenty novel 2-thioxo-1, 3-thiazolidin-4-one derivatives (5a-5t) were synthesized and evaluated for their antitubercular activity. The structure of the compounds was confirmed by IR, NMR and Mass Spectroscopy methods. In addition, single-crystal X-ray diffraction was performed for compound 5a. All the synthesized compounds were screened for their in-vitro antimycobacterial activity against MTB (H37RV, ATCC No: 27294) by Alamar Blue assay method. Compounds 5r, 5k, 5t displayed most potent in-vitro activity with MICs of 0.05, 0.1, 0.2 μg/ml concentrations respectively which are comparatively potent than the standards. Molecular docking and dynamics simulations were performed to find out the plausible mechanism of the titled compounds.

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A novel and clean synthesis of 5-benzylidene-2-thioxothiazolidin-4-ones and thiazolidine-2,4-diones has been achieved in good yields by condensation of aromatic aldehydes with rhodanine or thiazolidine-2,4-dione under microwave irradiation using glycine a

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E,Z-5-Arylmethylene-4-oxo-2-thioxo-1,3-thiazolidine and 3,3'-Dithiobis-2H-1-benzopyran-2-one Derivatives and their Reactions with Some Amines

The reaction of 4-oxo-2-thioxo-1,3-thiazolidine (1) with salicylaldehyde (2) or its 5-bromo derivative (2b) in acetic acid and sodium acetate gave a mixture of E,Z- or E-5-arylmethylene-4-oxo-2-thioxo-1,3-thiazolidines (3a or b) and 3,3'-dithiobis-2H-1-benzopyran-2-ones (4a and b), respectively. Treatment of E,Z-thiazolidinone (3a) with benzylamine or morpholine in dioxane at room temperature afforded 3-benzylamino-2H-1-benzopyran-2-one (6a) or E,Z-2-thiazolin-4-one derivative (7b) together with the amine salt (8), respectively. Similar treatment of E-(3b) with benzylamine yielded the E,Z-2-thiazolin-4-one derivative (7a) and the disulfide (4b) as the major product. The disulfide (4a) reacted with benzylamine in cold dioxane to yield the disulfide derivative (10) in addition to 6a whereas in boiling dioxane in gave 2H-1-benzopyran-2-one derivatives (6a and b). On the other hand, when E-(3b) or 4a was treated with dicyclohexylamine in dioxane, it gave 4b as well as the amine salt (9) in the former case and 3-mercapto-2H-1-benzopyran-2-one (5, X = H) in the latter one. Structures of all products were evidenced by microanalytical and spectra data.

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