566939-06-8

Basic information

• Product Name: 7-Oxa-2,4,11-triazadodecan-12-oic acid, 2-methyl-5-(1-methylethyl)-1-[2-(1-methylethyl)-5-thiazolyl]-3,6-dioxo-10- (phenylmethyl)-8-[(1S)-2-phenyl-1-[[(5-thiazolylmethoxy)carbonyl]amino] ethyl]-, 1,1-dimethylethyl ester, (5S,8S,10S)-
• CAS NO: 566939-06-8
• Molecular Formula: C42H56N6O7S2
• Molecular Weight: 821.075
• Mol File: 566939-06-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 7-Oxa-2,4,11-triazadodecan-12-oic acid, 2-methyl-5-(1-methylethyl)-1-[2-(1-methylethyl)-5-thiazolyl]-3,6-dioxo-10- (phenylmethyl)-8-[(1S)-2-phenyl-1-[[(5-thiazolylmethoxy)carbonyl]amino] ethyl]-, 1,1-dimethylethyl ester, (5S,8S,10S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Oxa-2,4,11-triazadodecan-12-oic acid, 2-methyl-5-(1-methylethyl)-1-[2-(1-methylethyl)-5-thiazolyl]-3,6-dioxo-10- (phenylmethyl)-8-[(1S)-2-phenyl-1-[[(5-thiazolylmethoxy)carbonyl]amino] ethyl]-, 1,1-dimethylethyl ester, (5S,8S,10S)-(566939-06-8)
• EPA Substance Registry System: 7-Oxa-2,4,11-triazadodecan-12-oic acid, 2-methyl-5-(1-methylethyl)-1-[2-(1-methylethyl)-5-thiazolyl]-3,6-dioxo-10- (phenylmethyl)-8-[(1S)-2-phenyl-1-[[(5-thiazolylmethoxy)carbonyl]amino] ethyl]-, 1,1-dimethylethyl ester, (5S,8S,10S)-(566939-06-8)

Safety Data

• Hazardous Substances Data: 566939-06-8(Hazardous Substances Data)

Upstream product

• 154212-59-6 5-(p-nitrophenyloxycarbonyloxymethyl)thiazole hydrochloride 
• 144163-85-9 (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 
• 154212-61-0 N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)-carbonyl)-L-valine 
• 162849-95-8 (2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane 

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.