182120-83-8

Basic information

• Product Name: 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carbothioamide
• Synonyms: 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carbothioamide
• CAS NO: 182120-83-8
• Molecular Weight: 273.38
• Mol File: 182120-83-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carbothioamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carbothioamide(182120-83-8)
• EPA Substance Registry System: 2-(tert-butoxycarbonylaminomethyl)-1,3-thiazole-4-carbothioamide(182120-83-8)

Safety Data

• Hazardous Substances Data: 182120-83-8(Hazardous Substances Data)

Usage

Molar mass

235.33 g/mol

Chemical structure

A thiazole ring with a tert-butoxycarbonyl group and an amino group attached to it

Potential applications

Pharmaceuticals, agrochemicals, and organic synthesis

Possible use

Building block in the synthesis of bioactive molecules and pharmaceutical agents

Safety

Proper handling and storage required to prevent adverse effects

Upstream product

• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 

Relevant articles and documents

RITA Mimics: Synthesis and Mechanistic Evaluation of Asymmetric Linked Trithiazoles

The established cytotoxic agent RITA contains a thiophene-furan-thiophene backbone and two terminal alcohol groups. Herein we investigate the effect of using thiazoles as the backbone in RITA-like molecules and modifying the terminal groups of these trithiazoles, thereby generating 41 unique structures. Incorporating side chains with varied steric bulk allowed us to investigate how size and a stereocenter impacted biological activity. Subjecting compounds to growth inhibition assays on HCT-116 cells showed that the most potent compounds 7d, 7e, and 7h had GI50 values of 4.4, 4.4, and 3.4 μM, respectively, versus RITA (GI50 of 800 nM). Analysis of these compounds in apoptosis assays proved that 7d, 7e, and 7h were as effective as RITA at inducing apoptosis. Evaluating the impact of 7h on proteins targeted by RITA (p53, c-Myc, and Mcl-1) indicated that it acts via a different mechanism of action to that of RITA. RITA suppressed Mcl-1 protein via p53, whereas compound 7h suppressed Mcl-1 expression via an alternative mechanism independent of p53.