124623-49-0

Basic information

• Product Name: (+/-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one
• CAS NO: 124623-49-0
• Molecular Weight: 304.8
• Mol File: 124623-49-0.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one(124623-49-0)
• EPA Substance Registry System: (+/-)-trans-5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one(124623-49-0)

Safety Data

• Hazardous Substances Data: 124623-49-0(Hazardous Substances Data)

Upstream product

• 16273-54-4 N-(3-Pyridylmethylidene)methylamine 
• 133692-27-0 methyl 2-(4-chlorophenyl)-2-mercaptoacetate 
• 114898-41-8 2-(4-chlorophenyl)-2-mercaptoacetic acid 
• 124624-76-6 (R)-(4-chlorophenyl)sulfanyl acetic acid 
• 124624-74-4 (S)-(4-chlorophenyl)sulfanyl acetic acid 
• 132906-96-8 (S)-Methyl (4-chlorophenyl)mercaptoacetate 

Relevant articles and documents

Synthetic Study of the Highly Potent and Selective Anti-platelet Activating Factor Thiazolidin-4-one Agents and related Compounds

Stereoselective cyclo-condensation of α-sulfanylcarboxylic acids (or esters) 6 with N-methylarylimines 7 afforded the title compounds, 2-arylthiazolidin-4-ones, some of which exhibit highly potent anti-PAF activity.The reaction without added catalyst gave predominantly cis products, however, when titanium(IV) isopropoxide was added as catalyst trans products were predominantly formed.Allylation of 3-methyl-2-(3-pyridyl)thiazolidin-4-one 22 with allyl bromide using lithium amides gave the trans-5-allyl-2-(3-pyridyl)thiazolidin-4-one 23 with good selectivity.To study the stereostructure-activity relationship, the four optically active isomers of 3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one 4 and 5-(4-chlorophenyl)-3-methyl-2-(3-pyridyl)thiazolidin-4-one 5 were synthesized.The absolute configurations of compounds 4 and 5 were determined by X-ray analyses and 1H NMR measurements.Epimerization of the 5-position of compounds 4 and 5 was found to be effected by bases with high regioselectivity (>99percent), which was checked by a cross-over experiment using several optically active compounds.

STEREOSELECTIVE SYNTHESIS OF ANTI-PAF ACTIVE THIAZOLIDIN-4-ONES VIA CYCLO-CONDENSATION OF ALKYL α-MERCAPTOCARBOXYLATES WITH ARYLIMINES

Two distinctive methods for the synthesis of cis- and trans-2,5-disubstituted thiazolidin-4-ones via stereoselective cyclo-condensation between α-mercaptocarboxylic esters and arylimines have been developed.With the new reaction used as the key step, two sets of optically active anti-PAF active thiazolidin-4-ones were synthesized.

STRUCTURE-ACTIVITY RELATIONSHIP OF OPTICALLY ACTIVE 2-(3-PYRIDYL)THIAZOLIDIN-4-ONES AS A PAF ANTAGONIST

Two sets of optically active 5-substituted-2-(3-pyridyl)thiazolidin-4-ones, highly potent and selective antagonists of platelet activation factor (PAF), displayed apparently different anti-PAF activities between their enantiomers, wherein these activities depend markedly on the absolute configuration of the 2-position in the thiazolidin-4-ones.