198904-13-1

Basic information

• Product Name: N-(Methoxycarbonyl)-L-tert-leucine N2-[2(S)-hydroxy-3(S)-[N-(methoxycarbonyl)-L-tert-leucylamino]-4-phenylbutyl]-N2-[4-(2-methyl-5-tetrazolyl)benzyl]hydrazide
• Synonyms: CGP-75176; methyl {(1S,4S,5S,10S)-4-benzyl-1,10-di-tert-butyl-5-hydroxy-7-[4-(2-methyl-2H-tetrazol-5-yl)benzyl]-2,9,12-trioxo-13-oxa-3,7,8,11-tetraazatetradec-1-yl}carbamate (non-preferred name)
• CAS NO: 198904-13-1
• Molecular Formula: C₃₅H₅₁N₉O₇
• Molecular Weight: 709.8355
• Mol File: 198904-13-1.mol

Chemical Properties

• Density: 1.25g/cm³
• Refractive Index: 1.593
• CAS DataBase Reference: N-(Methoxycarbonyl)-L-tert-leucine N2-[2(S)-hydroxy-3(S)-[N-(methoxycarbonyl)-L-tert-leucylamino]-4-phenylbutyl]-N2-[4-(2-methyl-5-tetrazolyl)benzyl]hydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Methoxycarbonyl)-L-tert-leucine N2-[2(S)-hydroxy-3(S)-[N-(methoxycarbonyl)-L-tert-leucylamino]-4-phenylbutyl]-N2-[4-(2-methyl-5-tetrazolyl)benzyl]hydrazide(198904-13-1)
• EPA Substance Registry System: N-(Methoxycarbonyl)-L-tert-leucine N2-[2(S)-hydroxy-3(S)-[N-(methoxycarbonyl)-L-tert-leucylamino]-4-phenylbutyl]-N2-[4-(2-methyl-5-tetrazolyl)benzyl]hydrazide(198904-13-1)

Safety Data

• Hazardous Substances Data: 198904-13-1(Hazardous Substances Data)

Upstream product

• 162537-11-3 (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid 
• 38446-81-0 4-(2-methyl-2H-tetrazol-5-yl)-benzaldehyde 
• 20859-02-3 L-tert-Leucine 
• 105-07-7 4-cyanobenzaldehyde 
• 74815-22-8 4-(2H-tetrazol-5-yl)benzaldehyde 
• 198904-72-2 N'-[4-(2-Methyl-2H-tetrazol-5-yl)-benzyl]-hydrazinecarboxylic acid tert-butyl ester 
• 198904-73-3 1-[4-(2-Methyl-2H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[(tert-butyloxycarbonyl)-amino]-6-phenyl-2-azahexane 
• 198904-12-0 1-[4-(tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[N-(N-methoxycarbonyl-(L)-tert-leucyl)amino]-6-phenyl-2-azahexane 
• 198905-17-8 1-[4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-4(S)-hydroxy-5(S)-2,5-bis[N-(N-methoxycarbonyl-(L)-tert-leucyl)amino]-6-phenyl-2-azahexane 
• 74-88-4 methyl iodide 

Relevant articles and documents

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.

ANTIVIRALLY ACTIVE HETEROCYCLIC AZAHEXANE DERIVATIVES

There are described compounds of formula I*, STR1 wherein R. sub.1 is lower alkoxycarbonyl,R 2 is secondary or tertiary lower alkyl or lower alkylthio-lower alkyl, R. sub.3 is phenyl that is unsubstituted or substituted by one or more lower alkoxy radicals, or C 4-C 8 cycloalkyl,R. sub.4 is phenyl or cyclohexyl each substituted in the 4-position by unsaturated heterocyclyl that is bonded by way of a ring carbon atom, has from 5 to 8 ring atoms, contains from 1 to 4 hetero atoms selected from nitrogen, oxygen, sulfur, sulfinyl (--SO--) and sulfonyl (--SO 2--) and is unsubstituted or substituted by lower alkyl or by phenyl-lower alkyl,R 5, independently of R 2, has one of the meanings mentioned for R 2, andR 6, independently of R. sub.1, is lower alkoxycarbonyl,or salts thereof, provided that at least one salt-forming group is present. The compounds are inhibitors of retroviral aspartate protease and can be used, for example, in the treatment of AIDS. They exhibit outstanding pharmacodynamic properties.