160232-45-1

Basic information

• Product Name: [(1S,2R)-1-Benzyl-3-(cyclopentylmethyl-amino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester
• CAS NO: 160232-45-1
• Molecular Weight: 362.513
• Mol File: 160232-45-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: [(1S,2R)-1-Benzyl-3-(cyclopentylmethyl-amino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(1S,2R)-1-Benzyl-3-(cyclopentylmethyl-amino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester(160232-45-1)
• EPA Substance Registry System: [(1S,2R)-1-Benzyl-3-(cyclopentylmethyl-amino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester(160232-45-1)

Safety Data

• Hazardous Substances Data: 160232-45-1(Hazardous Substances Data)

Upstream product

• 6053-81-2 cyclopentylmethylamine 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 
• 162536-42-7 (1S,2R)-(3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert butyl ester 
• 58714-85-5 cyclopropylmethyl-amine hydrochloride 
• 4254-02-8 cyclopentanecarbonitrile 

Downstream Products

• 160232-99-5 {(1S,2R)-1-Benzyl-3-[cyclopentylmethyl-(4-methoxy-benzenesulfonyl)-amino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 890904-65-1 N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-4-(E-hydroxyiminomethyl)-N-(cyclopentylmethyl)benzenesulfonamide 

Relevant articles and documents

Discovery of imidazolidine-2,4-dione-linked HIV protease inhibitors with activity against lopinavir-resistant mutant HIV

A new series of HIV protease inhibitors has been designed and synthesized based on the combination of the (R)-(hydroxyethylamino)sulfonamide isostere and the cyclic urea component of lopinavir. The series was optimized by replacing the 6-membered cyclic urea linker with an imidazolidine-2,4-dione which readily underwent N-alkylation to incorporate various methylene-linked heterocycle groups that bind favorably in site 3 of HIV protease. Significant improvements compared to lopinavir were seen in cell culture activity versus wild-type virus (pNL4-3) and the lopinavir-resistant mutant virus A17 (generated by in vitro serial passage of HIV-1 (pNL4-3) in MT-4 cells). Select imidazolidine-2,4-dione containing PIs were also more effective at inhibiting highly resistant patient isolates Pt1 and Pt2 than lopinavir. Pharmacokinetic data collected for compounds in this series varied considerably when coadministered orally in the rat with an equal amount of ritonavir (5 mg/kg each). The AUC values ranged from 0.144 to 12.33 μg h/mL.

Sulfonamide inhibitors of aspartyl protease

The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.