38825-42-2

Basic information

• Product Name: 4-Thiazolidinone, 3-(4-methylphenyl)-2-[(4-methylphenyl)imino]-
• CAS NO: 38825-42-2
• Molecular Formula: C17H16N2OS
• Molecular Weight: 296.393
• Mol File: 38825-42-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 4-Thiazolidinone, 3-(4-methylphenyl)-2-[(4-methylphenyl)imino]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolidinone, 3-(4-methylphenyl)-2-[(4-methylphenyl)imino]-(38825-42-2)
• EPA Substance Registry System: 4-Thiazolidinone, 3-(4-methylphenyl)-2-[(4-methylphenyl)imino]-(38825-42-2)

Safety Data

• Hazardous Substances Data: 38825-42-2(Hazardous Substances Data)

Upstream product

• 65252-01-9 S-methyl-N,N'-di-p-tolyl-isothiourea 
• 68-11-1 mercaptoacetic acid 
• 20584-08-1 S-ethyl-N,N'-di-p-tolyl-isothiourea 
• 73901-66-3 N,N-di-p-tolyl-thiourea 
• 79-08-3 bromoacetic acid 
• 79-11-8 chloroacetic acid 
• 105-39-5 chloroacetic acid ethyl ester 
• 621-01-2 N,N'-Bis(p-tolyl)thiourea 
• 106-49-0 p-toluidine 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 328271-98-3 5-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-3-p-tolyl-2-[(Z)-p-tolylimino]-thiazolidin-4-one 
• 328272-01-1 5-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-3-p-tolyl-2-[(Z)-p-tolylimino]-thiazolidin-4-one 
• 1228044-64-1 3-(5-((4-oxo-3-(4-methylphenyl)-2-(4-methylphenylimino)thiazolidin-5-ylidene)methyl)furan-2-yl)benzoic acid 
• 1229009-52-2 C₂₄H₁₉ClN₂OS 
• 56383-55-2 6-methylsulfanyl-3-p-tolyl-2-p-tolylimino-2,3-dihydro-[1,3]thiazin-4-one 

Relevant articles and documents

Novel thiazolidinone/thiazolo[3,2-a] benzimidazolone-isatin conjugates as apoptotic anti-proliferative agents towards breast cancer: One-pot synthesis and in vitro biological evaluation

In connection with our research program on the development of new isatin-based anticancer candidates, herein we report the synthesis of two novel series of thiazolidinone-isatin conjugates (4a–n) and thiazolo[3,2-a]benzimidazolone-isatin conjugates (7a–d), and in vitro evaluation of their antiproliferative activity towards two breast cancer cell lines; triple negative MDA-MB-231, and MCF-7. Compounds 4m and 7b emerged as the most active congeners against MDA-MB-231 cells (IC50 = 7.6 ± 0.5 and 13.2 ± 1.1 μM, respectively). Compounds 4m and 7b were able to provoke apoptosis in MDA-MB-231 cells, evidenced by the up-regulation of Bax and down-regulation of Bcl-2, besides boosting caspase-3 levels. Hybrid 4m induced a fourfold increase in the percentage of cells at Sub-G1, with concurrent arrest in G2-M phase by 2.5-folds. Furthermore, hybrid 4m resulted in a sixfold increase in the percentage of annexin V-FITC positive apoptotic MDA-MB-231 cells as compared with the control. Moreover, the cytotoxic activities of the active conjugates were assessed towards two nontumorigenic cell lines (breast MCF-10A and lung WI-38) where both conjugates 4m and 7b displayed mean tumor selectivity index: 9.6 and 13.9, respectively. Finally, several ADME descriptors were predicted for the active conjugates via a theoretical kinetic study.

An Environment-friendly Synthesis of 2,3-Disubstituted-2-iminothiazoline-4-ones

A series of 2,3-substituted-2-iminothiazoline-4-ones derivatives have been synthesized via an improved method including an auto-catalyzed reaction. This method avoided using any extra catalyst except for the reaction material. This method has been successful in both the aromatic substituted 2-iminothiazolines and the alkyl substituted 2-iminothiazolines. The special product with a hydroxyl group on the 2-iminogroup of 1,3-thiazoline-4-ones has also been obtained unexpectedly. The possible mechanism has been proposed for the special process of dealkylation and hydroxylation. This method offered a special way to afford the 2-hydroxyimino-substituted thiazoline-4-one derivatives in an efficient and eco-friendly way. The mechanism of the transformation under acid condition has also been proposed.

Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure-activity relationships

Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 μM) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 μM) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7- phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl)furan-2-yl)benzoic acid (1).