198904-02-8

Basic information

• Product Name: N-[(1S,2S)-1-benzyl-2-hydroxy-3-(2-{(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}-1-[4-(1,3-thiazol-2-yl)benzyl]hydrazino)propyl]-N~2~-(methoxycarbonyl)-L-valinamide
• Synonyms: butanoic acid, 2-[(methoxycarbonyl)amino]-3,3-dimethyl-, 2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]amino]-4-phenylbutyl]-2-[[4-(2-thiazolyl)phenyl]methyl]hydrazide, (2S)-; N-[(2S,3S)-3-hydroxy-4-(2-{(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}-1-[4-(1,3-thiazol-2-yl)benzyl]hydrazinyl)-1-phenylbutan-2-yl]-N~2~-(methoxycarbonyl)-L-valinamide
• CAS NO: 198904-02-8
• Molecular Formula: C₃₅H₄₈N₆O₇S
• Molecular Weight: 696.8566
• Mol File: 198904-02-8.mol
• Article Data: 1

Chemical Properties

• Density: 1.219g/cm³
• Refractive Index: 1.571
• CAS DataBase Reference: N-[(1S,2S)-1-benzyl-2-hydroxy-3-(2-{(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}-1-[4-(1,3-thiazol-2-yl)benzyl]hydrazino)propyl]-N~2~-(methoxycarbonyl)-L-valinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1S,2S)-1-benzyl-2-hydroxy-3-(2-{(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}-1-[4-(1,3-thiazol-2-yl)benzyl]hydrazino)propyl]-N~2~-(methoxycarbonyl)-L-valinamide(198904-02-8)
• EPA Substance Registry System: N-[(1S,2S)-1-benzyl-2-hydroxy-3-(2-{(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}-1-[4-(1,3-thiazol-2-yl)benzyl]hydrazino)propyl]-N~2~-(methoxycarbonyl)-L-valinamide(198904-02-8)

Safety Data

• Hazardous Substances Data: 198904-02-8(Hazardous Substances Data)

Upstream product

• 198904-60-8 N'-[(2S,3S)-2-Hydroxy-3-((S)-2-methoxycarbonylamino-3-methyl-butyrylamino)-4-phenyl-butyl]-N'-(4-thiazol-2-yl-benzyl)-hydrazinecarboxylic acid tert-butyl ester 
• 198904-58-4 N'-[(2S,3S)-2-Hydroxy-4-phenyl-3-(2,2,2-trifluoro-acetylamino)-butyl]-N'-(4-thiazol-2-yl-benzyl)-hydrazinecarboxylic acid tert-butyl ester 
• 198904-59-5 1-[4-(thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-(tert-butoxycarbonyl)amino-5(S)-amino-6-phenyl-2-azahexane 
• 198904-55-1 N-1-(tert-butyloxycarbonyl)-N-2-[4-(thiazol-2-yl)benzyl]hydrazine 
• 198904-53-9 4-(thiazol-2-yl)-benzaldehyde 
• 20859-02-3 L-tert-Leucine 
• 162537-11-3 (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid 
• 198904-61-9 1-[4-(thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5 (S)-N-(N-methoxycarbonyl-(L)-valyl)amino-6-phenyl-2-azahexane 
• 24856-58-4 1,1-dimethoxy-1-(4-bromophenyl)methane 

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.