756870-01-6

Basic information

• Product Name: 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester
• CAS NO: 756870-01-6
• Molecular Weight: 511.688
• Mol File: 756870-01-6.mol

Chemical Properties

• CAS DataBase Reference: 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester(756870-01-6)
• EPA Substance Registry System: 4-(4-{4-[1-(cyanomethyl-carbamoyl)-3-methyl-butylamino]-thiophen-3-yl}-phenyl)-piperazine-1-carboxylic acid tert-butyl ester(756870-01-6)

Safety Data

• Hazardous Substances Data: 756870-01-6(Hazardous Substances Data)

Upstream product

• 61-90-5 L-leucine 
• 756870-00-5 (S)-2-(4-Bromo-thiophen-3-ylamino)-4-methyl-pentanoic acid 
• 457613-78-4 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenylboronic acid 
• 459164-84-2 (S)-2-(4-Bromo-thiophen-3-ylamino)-4-methyl-pentanoic acid cyanomethyl-amide 

Relevant articles and documents

Rational design of potent and selective NH-linked aryl/heteroaryl cathepsin K inhibitors

Prior reports from our laboratories have identified the nonpeptidic inhibitor 2 as a potent and selective Cathepsin K (Cat K) inhibitor. Modelling studies suggested that the introduction of a NH linker between the P3 aryl and P2 leucinamide moieties would allow the formation of a H-bond with the Gly66 residue of Cat K, hopefully increasing potency. Aniline 4 was thus synthesized and showed improved potency over its predecessor 2. Further modelling concluded that a 2-substituted five membered ring could more adequately place the P3 moiety of 4 into the S3 pocket of Cat K. The synthesis of the 2-substituted thiophene 5 confirmed this hypothesis by displaying a slight increase in potency against Cat K (>10-fold increase in potency vs 2) and a good selectivity profile against Cathepsins B, L, and S. This rationally designed inhibitor 5 also displayed increased potency in a functional bone resorption assay (10nM) versus 2 (95nM).