189357-33-3

Basic information

• Product Name: (4R)-N-tert-butyl-3-[(2S,3S)-3-{[(2,6-dimethylphenoxy)acetyl]amino}-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide
• CAS NO: 189357-33-3
• Molecular Formula: C₃₀H₄₁N₃O₅S
• Molecular Weight: 555.7286
• Mol File: 189357-33-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 829.6°C at 760 mmHg
• Flash Point: 455.6°C
• Density: 1.181g/cm³
• Vapor Pressure: 3.61E-29mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: (4R)-N-tert-butyl-3-[(2S,3S)-3-{[(2,6-dimethylphenoxy)acetyl]amino}-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-N-tert-butyl-3-[(2S,3S)-3-{[(2,6-dimethylphenoxy)acetyl]amino}-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide(189357-33-3)
• EPA Substance Registry System: (4R)-N-tert-butyl-3-[(2S,3S)-3-{[(2,6-dimethylphenoxy)acetyl]amino}-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide(189357-33-3)

Safety Data

• Hazardous Substances Data: 189357-33-3(Hazardous Substances Data)

Usage

Description

(4R)-N-tert-butyl-3-[(2S,3S)-3-[(2,6-dimethylphenoxy)acetyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide is a thiazolidine derivative that belongs to the class of thiazolidinediones. It is characterized by the presence of a tert-butyl group, a phenyl group, and a phenoxyacetyl amino group. (4R)-N-tert-butyl-3-[(2S,3S)-3-[(2,6-dimethylphenoxy)acetyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide is known for its potential pharmacological properties as an insulin-sensitizing agent, which may be utilized in the treatment of type 2 diabetes.
Used in Pharmaceutical Industry:
(4R)-N-tert-butyl-3-[(2S,3S)-3-[(2,6-dimethylphenoxy)acetyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide is used as an insulin-sensitizing agent for the treatment of type 2 diabetes. Its chemical structure suggests that it may improve insulin sensitivity and lower blood glucose levels in diabetic patients, making it a promising candidate for further research and development in diabetes management.
Additionally, due to its unique chemical structure, this compound may have potential interactions with specific receptors or enzymes involved in glucose metabolism. This characteristic positions it as a candidate for exploration in the development of new therapeutic agents for diabetes management, potentially offering novel treatment options for patients suffering from this condition.

Upstream product

• 72778-00-8 (R)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
• 159000-71-2 Boc-Apns-Dmt-NHtBu 
• 148983-13-5 (R)-4-tert-Butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 117918-23-7 (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
• 158941-58-3 (R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 38930-22-2 methyl 2-(2,6-dimethylphenoxy)acetate 
• 1113-41-3 L-penicillamine 
• 576-26-1 2.6-dimethylphenol 
• 343330-18-7 N-(2-carboxy-ethyl)-succinamic acid 1-(4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carbonyl)-2-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-phenyl-propyl ester 
• 343330-19-8 N-carbamoylmethyl-succinamic acid 1-(4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carbonyl)-2-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-phenyl-propyl ester 
• 343330-17-6 N-carboxymethyl-succinamic acid 1-(4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carbonyl)-2-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-phenyl-propyl ester 
• 288399-78-0 KNI-1047 
• 288399-76-8 KNI-1039 
• 288399-77-9 KNI-1046 

Downstream Products

• 288399-78-0 KNI-1047 
• 288399-76-8 KNI-1039 
• 288399-77-9 KNI-1046 
• 288399-75-7 KNI-1038 
• 343330-18-7 N-(2-carboxy-ethyl)-succinamic acid 1-(4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carbonyl)-2-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-phenyl-propyl ester 
• 343330-19-8 N-carbamoylmethyl-succinamic acid 1-(4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carbonyl)-2-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-phenyl-propyl ester 
• 343330-17-6 N-carboxymethyl-succinamic acid 1-(4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carbonyl)-2-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-phenyl-propyl ester 
• 343330-26-7 2,2-Dimethyl-succinic acid 4-{(1S,2S)-1-((R)-4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carbonyl)-2-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-phenyl-propyl} ester 
• 343330-25-6 (R)-N-tert-butyl-3-[(2S,3S)-3-(2,6-dimethylphenoxyacetyl)amino-2-glutaryloxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 343330-15-4 (R)-N-tert-butyl-3-[(2S,3S)-3-(2,6-dimethylphenoxyacetyl)amino-2-succinyloxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 

Relevant articles and documents

Controlled drug release: New water-soluble prodrugs of an HIV protease inhibitor

We designed and synthesized a series of highly water-soluble prodrugs of an HIV protease inhibitor, KNI-727 (1), containing tandem-linked two auxiliary units, a solubilizing moiety and a self-cleavable spacer. Prodrugs with an ionized amino group at the solubilizing moiety exhibited a remarkable increase of water-solubility (>104 fold) compared to the parent drug 1. These prodrugs released 1 not enzymatically, but chemically via an intramolecular cyclization-elimination reaction through an imide formation in physiological conditions. Diversified rates of parent drug release were observed when the chemical structure of both the solubilizing and the spacer moieties were modified. This new approach for water-soluble prodrugs will enable to control chemically the release of parent drug as well as to maintain high water-solubility.

'Double-drugs' - A new class of prodrug form of an HIV protease inhibitor conjugated with a reverse transcriptase inhibitor by a spontaneously cleavable linker

We designed and synthesized a new series of prodrug-type anti-HIV agents consisting of a peptidomimetic HIV protease inhibitor conjugated with a nucleoside reverse transcriptase inhibitor in an effort to enhance the antiviral activity. For the conjugation, a series of linkers that conjoin the two different classes of inhibitors have been investigated. Conjugates using a succinyl amino acid linker were shown to release the parent components via the spontaneous imide formation at a faster rate compared to conjugates using a glutaryl amino acid linker, as expected from the energetically favorable cyclization to the five-membered ring. Herein, we report a new 'double-drug' 4b (KNI-1039) with a glutarylglycine linker, which exhibited extremely potent anti-HIV activity compared with that of the individual components. (C) 2000 Elsevier Science Ltd. All rights reserved.