1312794-01-6

Basic information

• Product Name: 2-(3-cyclopentyloxy-4-methoxyphenyl)-5-(piperidin-4-yl)-1,3,4-thiadiazole
• Synonyms: 2-(3-cyclopentyloxy-4-methoxyphenyl)-5-(piperidin-4-yl)-1,3,4-thiadiazole
• CAS NO: 1312794-01-6
• Molecular Weight: 359.492
• Mol File: 1312794-01-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(3-cyclopentyloxy-4-methoxyphenyl)-5-(piperidin-4-yl)-1,3,4-thiadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-cyclopentyloxy-4-methoxyphenyl)-5-(piperidin-4-yl)-1,3,4-thiadiazole(1312794-01-6)
• EPA Substance Registry System: 2-(3-cyclopentyloxy-4-methoxyphenyl)-5-(piperidin-4-yl)-1,3,4-thiadiazole(1312794-01-6)

Safety Data

• Hazardous Substances Data: 1312794-01-6(Hazardous Substances Data)

Upstream product

• 187834-88-4 tert-butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate 
• 124443-68-1 1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate 
• 1312794-00-5 tert-butyl 4-(5-(3-(cyclopentyloxy)-4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)piperidine-1-carboxylate 
• 1312793-98-8 tert-butyl 4-(2-(3-cyclopentyloxy-4-methoxybenzoyl)hydrazinecarbonyl)piperidine-1-carboxylate 
• 2971-79-1 isonipecotic acid methyl ester 

Relevant articles and documents

Synthesis of novel 1,2,4-oxadiazoles and analogues as potential anticancer agents

A library of 3,5-disubstituted-1,2,4-oxadiazoles 7-9 and their bioisosters, 1,3,4-oxadiazole 14 and 1,3,4-thiadiazole 16, were synthesized and evaluated in vitro for their anticancer potential against a panel of six human cancer cell lines. The key step in the synthesis of oxadiazoles 7-9 involve coupling of amidoxime 6 with an appropriate carboxylic acid followed by thermal cyclization. The bioisosteres, 1,3,4-oxadiazole 14 and 1,3,4-thiadiazole 16 were prepared from the reaction of a common precursor diacylhydrazine 13 with thionyl chloride and Lawesson′s reagent, respectively. The anticancer studies on the synthesized compounds revealed that presence of a cyclopentyloxy or n-butyloxy on the C-3 aryl ring and piperdin-4-yl or trichloromethyl at the C-5 position of 1,2,4-oxadiazole is essential for good activity. In particular, 1,2,4-oxadiazole 7i and analogue 1,3,4-thiadiazole 16 exhibited significant activity against DU145 (IC50: 9.3 μM) and MDA-MB-231 (IC 50: 9.2 μM) cell lines, respectively.