68301-50-8

Usage

Functional Groups

Amino group (NH?) attached to the thiazole ring
Carboxylic acid ethyl ester group (COOCH?CH?) attached to the thiazole ring
4-nitrophenyl substituent (NO?C?H?) attached to the thiazole ring

Structure

Contains a thiazole ring with amino and carboxylic acid ethyl ester groups, along with a 4-nitrophenyl substituent.

Use

Commonly employed in pharmaceutical research and drug development.

Therapeutic Applications

Studied for antibacterial, antifungal, and antitumor properties.

Potential Drug

Under investigation for potential use in treating various diseases.

Building Block

Valuable for synthesizing other organic compounds with similar properties and applications.

Upstream product

• 74476-72-5 ethyl 2-chloro-3-(4-nitrophenyl)-3-oxopropanoate 
• 17356-08-0 thiourea 
• 838-57-3 ethyl 4-nitrobenzoylacetate 
• 99983-34-3 ethyl 2-bromo-3-(4-nitrophenyl)-3-oxopropanoate 

Downstream Products

• 74476-62-3 ethyl 2-chloro-4-p-nitrophenyl-5-thiazolecarboxylate 

Relevant academic research and scientific papers

I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea

A concise and efficient one-pot process from easily available methyl ketones/unsaturated methyl ketones and thiourea was developed for the synthesis of 2-aminothiazoles under the media of I2/CuO. The method can highly stereoselectivity obtain the E-isomers of 4-ethenyl-2-aminothiazoles (5a-f). All these target molecules were characterized by NMR, HRMS and IR spectra. Furthermore, the target compounds 3c and 5b were further determined by X-ray crystallographic analysis.

Studies on Cerebral Protective Agents. VIII. Synthesis of 2-Aminothiazoles and 2-Thiazolecarboxamides with Anti-anoxic Activity

Various 2-aminothiazoles (2a-s and 3a-g) and 2-thiazolecarboxamides (4a-h), possessing a nitrogeneous basic moiety at the C-2 position of the thiazole ring, were prepared and tested for anti-anoxic (AA) activity in mice.Among them, N-4-(3-trifluoromethylphenyl)-2-thiazolecarbaxamide hydrochloride (4e, FR108143) (minimum effective doses of 3,2 mg/kg i.p. and 10 mg/kg p.o., respectively) exhibited more potent AA activity than either FK360 or compound 1, each of which has a nitrogeneous basic moiety at the C-5 position.The structure-activity relationship with regard to AA activity of this series of compounds are discussed, and the three-dimensional electrostatic potentials (3D-MEP) around the basic nitrogen atom of FK360 and the thiazole derivative (4e) are compared.Key words cerebral protective agent; anti-anoxia; 2-aminothiazole; 2-thiazolecarboxamide; structure-activity relationship; FK360

Syntheses and Reactions of 2-Halo-5-thiazolecarboxylates

A variety of 2-halo-5-thiazolecarboxylates was prepared from substituted-3-aminoacrylates and 3-ketoesters.Selective reduction of 2-chloro-5-thiazolecarboxylates 4a, 4i and 4j with sodium borohydride in ethanol provided the corresponding 2-halo-5-thiazolemethanols 27 - 29.Nucleophilic displacement on methyl methanesulfonate (32c) occured selectivity at the 5-substituent to provide 2-chloro-4-(trifluoromethyl)-5-(heteroatom-substituted methyl)thiazoles 32d-f.