144060-97-9

Basic information

• Product Name: ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• Synonyms: ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate;Ethyl 2-(3-Cyano-4-Isobutoxyphenyl)-4-Methyl-1,3-Thiazole-5-Carboxylate;Febuxostat Descyano Ethyl Ester;ethyl 2-(4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• CAS NO: 144060-97-9
• Molecular Formula: C₁₇H₂₁NO₃S
• Molecular Weight: 319.42
• EINECS: -0
• Mol File: 144060-97-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 438.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.132±0.06 g/cm3(Predicted)
• PKA: 1.61±0.10(Predicted)
• CAS DataBase Reference: ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate(144060-97-9)
• EPA Substance Registry System: ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate(144060-97-9)

Safety Data

• Hazardous Substances Data: 144060-97-9(Hazardous Substances Data)

Usage

Description

Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate is a chemical compound with a complex structure, characterized by its cyano and isobutoxyphenyl groups, as well as its thiazole and carboxylate functional groups. This molecule is known for its potential applications in various industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
Ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate is used as an impurity in the production of Febuxostat (F229000), a xanthine oxidase/xanthine dehydrogenase inhibitor. Febuxostat is utilized for the treatment of hyperuricemia and chronic gout, with dosages ranging from 40-120 mg/day proven effective in lowering serum urate levels in patients.
In the pharmaceutical industry, ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate plays a crucial role in the development and manufacturing of Febuxostat, a drug that helps manage hyperuricemia and chronic gout by inhibiting the enzymes responsible for uric acid production. ethyl 2-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate's presence as an impurity in Febuxostat production highlights its importance in the pharmaceutical sector, contributing to the development of effective treatments for gout and hyperuricemia.

Upstream product

• 161797-99-5 (2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylic acid ethyl ester) 
• 78-77-3 Isobutyl bromide 

Downstream Products

• 1206550-99-3 2-(4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid 
• 144060-62-8 2-[3-formyl-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic acid 

Relevant articles and documents

Design, synthesis, in silico and in vitro studies of novel 4-methylthiazole-5-carboxylic acid derivatives as potent anti-cancer agents

Since inhibitors of mucin onco proteins are potential targets for breast cancer therapy, a series of novel 4-methylthiazole-5-carboxylic acid (1) derivatives 3a-k were synthesized by the reaction of 1 with SOCl2followed by different bases/alcohols in the presence of triethylamine. Once synthesized and characterized, their binding modes with MUC1 were studied by molecular docking analysis using Aruglab 4.0.1 and QSAR properties were determined using HyperChem. All synthesized compounds were screened for in vitro anti-breast cancer activity against MDA-MB-231 breast adenocarcinoma cell lines by Trypan-blue cell viability assay and MTT methods. Compounds 1, 3b, 3d, 3e, 3i and 3f showed good anti-breast cancer activity. Since 1 and 3d exhibited high potent activity against MDA-MB-231 cell lines, they show could be effective mucin onco protein inhibitors.