147318-83-0

Basic information

• Product Name: [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester
• Synonyms: [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester
• CAS NO: 147318-83-0
• Molecular Weight: 465.614
• Mol File: 147318-83-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester(147318-83-0)
• EPA Substance Registry System: [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester(147318-83-0)

Safety Data

• Hazardous Substances Data: 147318-83-0(Hazardous Substances Data)

Upstream product

• 148982-94-9 N-tert-butyl-3-(tert-butoxycarbonyl)thiazolidine-4-carboxamide 
• 62023-65-8 (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 128019-19-2 (R)-N-tert-butyl-1,3-thiazolidine-4-carboxamide 

Downstream Products

• 169752-78-7 [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid benzyl ester 
• 790186-58-2 (S)-2-Amino-3-methyl-butyric acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 705247-31-0 (R)-2-Amino-3-methylsulfanyl-propionic acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 169752-79-8 (R)-2-tert-Butoxycarbonylamino-3-methylsulfanyl-propionic acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 178986-88-4 (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 566939-07-9 (S)-2-tert-Butoxycarbonylamino-pentanoic acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 178986-90-8 (S)-2-[2-(Isoquinolin-5-yloxy)-acetylamino]-3-methyl-butyric acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 178986-94-2 (S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyric acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 178986-93-1 (R)-3-Methylsulfanyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-propionic acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 566939-10-4 (S)-2-[2-(Isoquinolin-5-yloxy)-acetylamino]-pentanoic acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 169752-80-1 (R)-2-[2-(Isoquinolin-5-yloxy)-acetylamino]-3-methylsulfanyl-propionic acid (1S,2S)-2-benzyloxycarbonylamino-1-((R)-4-tert-butylcarbamoyl-thiazolidine-3-carbonyl)-3-phenyl-propyl ester 
• 1054667-47-8 Acetic acid 3-[(1S,2S)-1-benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-propyl-phenyl ester 
• 1054609-05-0 Acetic acid 3-[(1S,2S)-1-benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-ethyl-phenyl ester 
• 1053258-94-8 Acetic acid 3-[(1S,2S)-1-benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-methyl-phenyl ester 

Relevant articles and documents

Kynostatin (KNI)-227 and -272, highly potent anti-HIV agents: Conformationally constrained tripeptide inhibitors of HIV protease containing allophenylnorstatine

Selective and potent HIV protease inhibitors containing allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid] as a transition-state mimic were designed and synthesized. Among them, conformationally constrained tripeptide derivatives,

Structure-activity relationship of orally potent tripeptide-based HIV protease inhibitors containing hydroxymethylcarbonyl isostere

We designed and synthesized a new class of peptidomimetic human immunodeficiency virus protease inhibitors containing a unique unnatural amino acid, allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid], with a hydroxymethylcarbonyl isostere as the active moiety. From a structure-activity relationship study of HIV-1 protease inhibition, enzyme selectivity for other aspartyl proteases, the antiviral activity and pharmacokinetics in rats, 24c (KNI-227) and 24d (KNI-272, our first clinical candidate) were found to be selective and orally potent HIV protease inhibitors. Moreover, an improvement of the pharmacokinetic features of KNI-272 provided two long-lasting and highly bioavailable compounds (24g: JE-2178,h: JE-2179).