1621105-16-5

Basic information

• Product Name: allyl (S)-4-(N-benzyl-2-((tert-butoxycarbonyl)amino)-4-methoxy-4-oxobutanamido)-4-(benzylcarbamoyl)piperidine-1-carboxylate
• Synonyms: allyl (S)-4-(N-benzyl-2-((tert-butoxycarbonyl)amino)-4-methoxy-4-oxobutanamido)-4-(benzylcarbamoyl)piperidine-1-carboxylate
• CAS NO: 1621105-16-5
• Molecular Weight: 636.745
• Mol File: 1621105-16-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: allyl (S)-4-(N-benzyl-2-((tert-butoxycarbonyl)amino)-4-methoxy-4-oxobutanamido)-4-(benzylcarbamoyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: allyl (S)-4-(N-benzyl-2-((tert-butoxycarbonyl)amino)-4-methoxy-4-oxobutanamido)-4-(benzylcarbamoyl)piperidine-1-carboxylate(1621105-16-5)
• EPA Substance Registry System: allyl (S)-4-(N-benzyl-2-((tert-butoxycarbonyl)amino)-4-methoxy-4-oxobutanamido)-4-(benzylcarbamoyl)piperidine-1-carboxylate(1621105-16-5)

Safety Data

• Hazardous Substances Data: 1621105-16-5(Hazardous Substances Data)

Upstream product

• 88333-03-3 Benzyl isocyanide 
• 59768-74-0 (S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester 
• 100-46-9 benzylamine 
• 306296-67-3 1-allyloxycarbonylpiperidin-4-one 

Downstream Products

• 1621105-54-1 methyl (S)-4-(benzyl(4-(benzylcarbamoyl)piperidin-4-yl)amino)-3-((tert-butoxycarbonyl)amino-4-oxobutanoate) 

Relevant articles and documents

Discovery and SAR studies of a novel class of cytotoxic 1,4-disubstituted piperidines via Ugi reaction

Herein we report a novel class of 1,4-disubstituted piperidines as potential anticancer agents. One-step and efficient synthesis of a structurally diverse library of piperidine-based analogs with five points of diversity has been developed using the Ugi four-component reaction. A structure-activity relationship (SAR) study showed that the presence of a benzyl or a Boc group at the N-1 position together with two or three aromatic groups at the C-4 position of the piperidine ring are important for optimal cytostatic properties. Compounds 20, 22, 27 and 29 were found to be the most potent with a 50% inhibitory concentration (IC50) ranging between 3 and 9.5 μM in the cancer cell lines evaluated. The NCI60 screen confirmed this 50% cytostatic concentration range for compound 20, irrespective of the nature of the tumor cell lines evaluated. The NCI COMPARE algorithm did not show any significant correlation between the growth inhibition profile of compound 20 with the NCI database compound profiles suggesting a potential novel mechanism of action.