178986-93-1

Basic information

• Product Name: (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
• Synonyms: (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
• CAS NO: 178986-93-1
• Molecular Weight: 800.997
• Mol File: 178986-93-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(178986-93-1)
• EPA Substance Registry System: (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(178986-93-1)

Safety Data

• Hazardous Substances Data: 178986-93-1(Hazardous Substances Data)

Upstream product

• 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 
• 147318-83-0 [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 158941-63-0 (R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-1,3-thiazolidine-4-carboxamide 
• 148982-94-9 N-tert-butyl-3-(tert-butoxycarbonyl)thiazolidine-4-carboxamide 
• 128019-19-2 (R)-N-tert-butyl-1,3-thiazolidine-4-carboxamide 
• 62023-65-8 (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 
• 2976-75-2 1-Naphthoxyacetic acid 
• 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 
• 169752-78-7 [(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid benzyl ester 

Relevant articles and documents

New water-soluble prodrugs of HIV protease inhibitors based on O→N intramolecular acyl migration

To improve the low water-solubility of HIV protease inhibitors, we synthesized water-soluble prodrugs of KNI-272 and KNI-279 which are potent HIV-1 protease inhibitors consisting of an Apns-Thz core structure (Apns; allophenylnorstatine, Thz; thiazolidine-4-carboxylic acid) as an inhibitory machinery. The prodrugs, which contained an O-acyl peptidomimetic structure with an ionized amino group leading to the increase of water-solubility, were designed to regenerate the corresponding parent drugs based on the O→N intramolecular acyl migration reaction at the α-hydroxy-β-amino acid residue, that is allophenylnorstatine. The synthetic prodrugs 3, 4, 6, and 7 improved the water-solubility (>300 mg/mL) more than 4000-fold in comparison with the parent compounds, which is the practically acceptable value as water-soluble drugs. These prodrugs were stable as an HCl salt and in a strongly acidic solution corresponding to gastric juice (pH 2.0), and could be converted to the parent compounds promptly in the aqueous condition from slightly acidic to basic pH at 37°C, with the suitable migration rate, via a five-membered ring intermediate. Using a similar method, we synthesized a prodrug (12) of ritonavir, a clinically useful HIV-1 protease inhibitor as an anti-AIDS drug. In contrast to the prodrugs 3, 4, 6, and 7, the prodrug 12 was very slowly converted to ritonavir probably through a six-membered ring intermediate, with the t1/2 value of 32 h that may not be suitable for practical use.