213179-53-4

Basic information

• Product Name: (S)-3-(4-Cyano-phenyl)-N-cyclopentyl-N-methyl-2-(5,6,7,8-tetrahydro-naphthalene-2-sulfonylamino)-propionamide
• CAS NO: 213179-53-4
• Molecular Weight: 465.616
• Mol File: 213179-53-4.mol

Chemical Properties

• CAS DataBase Reference: (S)-3-(4-Cyano-phenyl)-N-cyclopentyl-N-methyl-2-(5,6,7,8-tetrahydro-naphthalene-2-sulfonylamino)-propionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(4-Cyano-phenyl)-N-cyclopentyl-N-methyl-2-(5,6,7,8-tetrahydro-naphthalene-2-sulfonylamino)-propionamide(213179-53-4)
• EPA Substance Registry System: (S)-3-(4-Cyano-phenyl)-N-cyclopentyl-N-methyl-2-(5,6,7,8-tetrahydro-naphthalene-2-sulfonylamino)-propionamide(213179-53-4)

Safety Data

• Hazardous Substances Data: 213179-53-4(Hazardous Substances Data)

Upstream product

• 119-64-2 tetralin 
• 104-85-8 para-methylbenzonitrile 
• 184771-40-2 (2S)-2-(N-tert-butoxycarbonyl)-amino-N-cyclopentyl-3-(4-cyanophenyl)-N-methylpropanamide 
• 146664-08-6 N-acetyl-4-cyano-D,L-phenylalanine 
• 167479-78-9 (S)-4-Cyanophenylalanine 
• 61551-49-3 5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride 
• 17201-43-3 4-cyanobenzyl bromide 
• 131724-45-3 (S)-2-((tert-butoxycarbonyl)amino)-3-(4-cyanophenyl)propanoic acid 

Relevant articles and documents

Fluorobenzamidrazone thrombin inhibitors: Influence of fluorine on enhancing oral absorption

LB30057 (1) is a selective and efficacious oral thrombin inhibitor. Fluorine-substitution on the phenylene ring of the benzamidrazone portion in both compound 1 and its derivatives gave, in many cases, enhanced oral absorption in rats while maintaining the intrinsic potency and selectivity. Compound 2 demonstrated a 3-fold increase in absorption.

Structural modification of an orally active thrombin inhibitor, LB30057: Replacement of the D-pocket-binding naphthyl moiety

An amidrazonophenylalanine derivative LB30057 (2) was identified as a potent (K(i)=0.38nM), selective, and orally active thrombin inhibitor. As a continuation of studies into benzamidrazone-based thrombin inhibitors, we have structurally modified compound 2 by replacing the naphthyl group with a variety of hydrophobic moieties. This study led to discovery of several compounds with significantly enhanced potency in thrombin inhibition without sacrificing selectivity against trypsin and oral absorption. The highest activity was obtained with compound 23 (K(i)=0.045nM). Copyright (C) 1998 Elsevier Science Ltd.