198904-73-3

Basic information

• Product Name: 1-[4-(2-Methyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[(tert-butyloxycarbonyl)-amino]-6-phenyl-2-azahexane
• Synonyms: 1-[4-(2-Methyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[(tert-butyloxycarbonyl)-amino]-6-phenyl-2-azahexane
• CAS NO: 198904-73-3
• Molecular Weight: 567.688
• Mol File: 198904-73-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-[4-(2-Methyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[(tert-butyloxycarbonyl)-amino]-6-phenyl-2-azahexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(2-Methyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[(tert-butyloxycarbonyl)-amino]-6-phenyl-2-azahexane(198904-73-3)
• EPA Substance Registry System: 1-[4-(2-Methyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[(tert-butyloxycarbonyl)-amino]-6-phenyl-2-azahexane(198904-73-3)

Safety Data

• Hazardous Substances Data: 198904-73-3(Hazardous Substances Data)

Upstream product

• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 74815-22-8 4-(2H-tetrazol-5-yl)benzaldehyde 
• 105-07-7 4-cyanobenzaldehyde 
• 870-46-2 t-butoxycarbonylhydrazine 
• 38446-81-0 4-(2-methyl-2H-tetrazol-5-yl)-benzaldehyde 
• 198904-72-2 N'-[4-(2-Methyl-2H-tetrazol-5-yl)-benzyl]-hydrazinecarboxylic acid tert-butyl ester 

Downstream Products

• 198904-13-1 CGP 75176 

Relevant articles and documents

Intermediates for the preparation of peptide analogues

The invention relates to a novel process for the preparation of compounds of formula I STR1 wherein R1 is hydrogen or a suitable amino-protecting group, R2 is unsubstituted or substituted alkyl, R3 is hydrogen, aryl, heterocyclyl, unsubstituted or substituted alkyl or unsubstituted or substituted cycloalkyl, R4, independently of R1, is hydrogen or a suitable amino-protecting group and m is a number from 1 to 7; and wherein further suitable protecting groups for functional groups may be present; which compounds are antivirally active or can be used as starting materials for pharmaceutically active, especially antiviral compounds. The precursor is an oxo compound, which is in turn prepared by hydrogenation with a suitable complex hydride or with hydrogen in the presence of a suitable catalyst and acyl migration starting from a hydrazone, which is in turn preferably prepared from a nitrile via an imino compound by means of hydrogenation and reaction with a hydrazine derivative, which is prepared from an aldehyde by reaction with a reactive derivative of a carboxylic acid in the presence of a cyanide salt; and the novel intermediates required therefor.

New aza-dipeptide analogues as potent and orally absorbed HIV-1 protease inhibitors: Candidates for clinical development

On the basis of previously described X-ray studies of an enzyme/aza- dipeptide complex, aza-dipeptide analogues carrying N-(bis-aryl-methyl) substituents on the (hydroxethyl)hydrazine moiety have been designed and synthesized as HIV-1 protease inhibitors. By using either equally (12) or orthogonally (13) protected dipeptide isosteres, symmetrically and asymmetrically acylated aza-dipeptides can be synthesized. This approach led to the discovery of very potent inhibitors with antiviral activities (ED50) in the subnanomolar range. Acylation of the (hydroxethyl)hydrazine dipeptide isostere with the L-tert-leucine derivative 29 increased the oral bioavailability significantly when compared to the corresponding L-valine or L-isoleucine derivatives. The bis (L-tert-leucine) derivatives CGP 75355, CGP 73547, CGP 75136, and CGP 75176 combine excellent antiviral activity with high blood concentration after oral administration. Furthermore, they show no cross-resistance with saquinavir-resistant strains and maintain activity against indinavir-resistant ones. Consequently they qualify for further profiling as potential clinical candidates.