198903-87-6

Basic information

• Product Name: N-[(1S,2S)-1-benzyl-2-hydroxy-3-(2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-1-[4-(1,3-thiazol-5-yl)benzyl]hydrazino)propyl]-N~2~-(methoxycarbonyl)-3-methyl-L-valinamide
• Synonyms: butanoic acid, 2-[(methoxycarbonyl)amino]-3-methyl-, 2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethyl-1-oxobutyl]amino]-4-phenylbutyl]-2-[[4-(5-thiazolyl)phenyl]methyl]hydrazide, (2S)-; N-[(2S,3S)-3-hydroxy-4-(2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-1-[4-(1,3-thiazol-5-yl)benzyl]hydrazinyl)-1-phenylbutan-2-yl]-N~2~-(methoxycarbonyl)-3-methyl-L-valinamide
• CAS NO: 198903-87-6
• Molecular Formula: C₃₅H₄₈N₆O₇S
• Molecular Weight: 696.8566
• Mol File: 198903-87-6.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-methylbutanoyl}-1-[4-(1,3-thiazol-5-yl)benzyl]hydrazino)propyl]-N~2~-(methoxycarbonyl)-3-methyl-L-valinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1S,2S)-1-benzyl-2-hydroxy-3-(2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-1-[4-(1,3-thiazol-5-yl)benzyl]hydrazino)propyl]-N~2~-(methoxycarbonyl)-3-methyl-L-valinamide(198903-87-6)
• EPA Substance Registry System: N-[(1S,2S)-1-benzyl-2-hydroxy-3-(2-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-1-[4-(1,3-thiazol-5-yl)benzyl]hydrazino)propyl]-N~2~-(methoxycarbonyl)-3-methyl-L-valinamide(198903-87-6)

Safety Data

• Hazardous Substances Data: 198903-87-6(Hazardous Substances Data)

Upstream product

• 111398-44-8 N-methoxycarbonyl-L-valine 
• 198904-48-2 ((S)-1-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-thiazol-5-yl-benzyl)-hydrazino]-propylcarbamoyl}-2,2-dimethyl-propyl)-carbamic acid methyl ester 
• 20859-02-3 L-tert-Leucine 
• 1122-91-4 4-bromo-benzaldehyde 
• 198904-40-4 4-(thiazol-5-yl)benzaldehyde 
• 162537-11-3 (S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid 
• 198904-42-6 N-1-(tert-butyloxycarbonyl)-N-2-[4-(thiazol-5-yl)benzyl]hydrazine 
• 198904-46-0 1-[4-(thiazol-5-yl)-phenyl]-4(S)-hydroxy-2-(tert-butoxycarbonyl)amino-5(S)-amino-6-phenyl-2-azahexane 
• 198904-45-9 N'-[(2S,3S)-2-Hydroxy-4-phenyl-3-(2,2,2-trifluoro-acetylamino)-butyl]-N'-(4-thiazol-5-yl-benzyl)-hydrazinecarboxylic acid tert-butyl ester 
• 198904-47-1 N'-[(2S,3S)-2-Hydroxy-3-((S)-2-methoxycarbonylamino-3,3-dimethyl-butyrylamino)-4-phenyl-butyl]-N'-(4-thiazol-5-yl-benzyl)-hydrazinecarboxylic acid tert-butyl ester 

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.