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 
• 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 
• 98760-08-8 (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester 

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

Synthesis, antiviral activity, and pharmacokinetic evaluation of P3 pyridylmethyl analogs of oximinoarylsulfonyl HIV-1 protease inhibitors

As a continuation of the recently communicated discovery of oximinoarylsulfonamides as potent inhibitors of HIV-1 aspartyl protease, compounds bearing pyridylmethyl substituents at P3 were designed and synthesized. Potent analogs in this series provided low single-digit nanomolar EC50 values against both wild-type HIV and resistant mutant virus (A17), attenuated some 3- to 12-fold in the presence of 50% human serum. Pharmacokinetic results for compounds in this series showed good to excellent exposure when co-administered orally with an equal amount of ritonavir (5 mg/kg each) in the rat, with average AUC >8 μg h/mL. Similar dosing in dog resulted in significantly lower plasma levels (average AUC i = 2.4 nM).

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.