68199-62-2

Upstream product

• 501-53-1 benzyl chloroformate 
• 72-18-4 L-valine 
• 870-46-2 t-butoxycarbonylhydrazine 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 

Downstream Products

• 16305-24-1 N-Cholesteryloxycarbonyl-Phe-Val-tert.-butyloxycarbonyl-hydrazid 
• 16305-23-0 N-Benzyloxycarbonyl-Phe-Val-tert.-butyloxycarbonyl-hydrazid 
• 180463-23-4 {(S)-1-[N'-((2S,3S)-3-{(S)-3-Carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-2-hydroxy-4-phenyl-butyl)-N'-isobutyl-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid benzyl ester 
• 180463-09-6 (S)-N¹-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-isobutyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide 
• 180463-07-4 {(1S,2S)-1-Benzyl-3-[N'-((S)-2-benzyloxycarbonylamino-3-methyl-butyryl)-N-isobutyl-hydrazino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 180463-08-5 {(S)-1-[N'-((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-N'-isobutyl-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid benzyl ester 
• 180463-06-3 [(S)-1-(N'-Isobutyl-hydrazinocarbonyl)-2-methyl-propyl]-carbamic acid benzyl ester 
• 2443-71-2 benzyl (S)-(1-hydrazineyl-3-methyl-1-oxobutan-2-yl)carbamate 

Relevant academic research and scientific papers

Carbonylhydrazide-based molecular tongs inhibit wild-type and mutated HIV-1 protease dimerization

We have designed and synthesized new molecular tongs based on a rigid naphthalene scaffold and evaluated their antidimer activity on HIV-1 protease (PR). We inserted carbonylhydrazide and oligohydrazide (azatide) fragments into their peptidomimetic arms t

Acyl hydrazines as precursors to acyl radicals

The use of acyl hydrazines (hydrazides) as precursors for the stoichiometric generation of acyl radicals is explored. Two classes of substrates are examined: unsubstituted acyl hydrazines and acyl hydrazines substituted with a leaving group (2-nitrobenzenesulfonyl or 'nosyl'). Both types are successfully converted to acyl radicals, and are then trapped by nitroxide radicals to give acyloxyamine products. Cyclization reactions are demonstrated for both classes of substrates. A low temperature modification of the McFayden-Stevens reaction is also developed.

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.