57699-55-5

Upstream product

• 57699-48-6 3-(4-Hydroxybenzyliden)-carbazinsaeure-tert-butylester 
• 870-46-2 t-butoxycarbonylhydrazine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 57699-48-6 N-t-butoxycarbonyl-N'-4-hydroxybenzaldehyde hydrazone 
• 52211-82-2 4-hydroxylbenzaldehyde hydrazone 

Downstream Products

• 161852-52-4 N'-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-N'-(4-hydroxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester 
• 512835-55-1 N-t-butoxycarbonyl-azatyrosine ethyl ester 
• 934-53-2 cumenyl chloride 

Relevant academic research and scientific papers

The efficient synthesis of azaamino acids

An efficient method of synthesis of N-t-butoxycarbonyl-azaamino acid ethyl esters has been described. This method consisted of three stages including: hydrazone formation, its reduction and acylation with ethyl chloroformate. The second step - reduction of the hydrazones to the appropriate hydrazides - was the most challenging. Some reducing agents have been tested, though NaBH3CN was found to lead to the final products with the highest yields in relatively short time and even to allow the selective reduction of C-N bond in the presence of nitro group.

Antiretroviral hydrazine derivatives

The invention relates to compounds of formula STR1 and salts, pharmaceutical compositions, intermediates and processes of preparation thereof.

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.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A retroviral protease inhibiting compound of the formula: STR1 is disclosed wherein R 1, R 2, R 5, R 6, Y m and Y' n are herein defined.