161852-52-4

Basic information

• Product Name: N'-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-N'-(4-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester
• CAS NO: 161852-52-4
• Molecular Weight: 501.623
• Mol File: 161852-52-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N'-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-N'-(4-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N'-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-N'-(4-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester(161852-52-4)
• EPA Substance Registry System: N'-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-N'-(4-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester(161852-52-4)

Safety Data

• Hazardous Substances Data: 161852-52-4(Hazardous Substances Data)

Upstream product

• 57699-55-5 N-t-butoxycarbonyl-N'-4-hydroxybenzyl hydrazine 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 

Relevant articles and documents

Aza-peptide analogs as potent human immunodeficiency virus type-1 protease inhibitors with oral bioavailability

A series of aza-peptide analogs with a (hydroxyethyl)hydrazine isostere has been synthesized as HIV-1 protease inhibitors using a simple synthetic scheme. Structure-activity studies based on the X-ray of a previously described inhibitor-enzyme complex led to potent inhibitors with antiviral activity in the low-nanomolar range. The S-configuration of the transition- state hydroxyl group was preferred in this series. Small modifications of the P2P3 and P2'P3' substituents had little effect on enzyme inhibition but greatly influenced the pharmacokinetic profile. As a result of these studies, the symmetrically acylated compound 8a and its close analog 24a bearing a methyl carbamate in P3 and an ethyl carbamate in P3' position were identified as potent inhibitors with plasma concentrations exceeding antiviral ED50 values 150-fold following oral application in mice.