3810-35-3

Basic information

• Product Name: tenonitrozole
• Synonyms: tenonitrozole;2-(alpha-thenoylamino)-2-nitro-5-thiazole;ALPHA-THENOYLAMINO-2-NITRO-5-THIAZOLE;Atrican;N-(5-Nitro-2-thiazolyl)-2-thiophenecarboxamide;TC-109;Thenitrazole;N-(5-nitro-1,3-thiazol-2-yl)thiophene-2-carboxamide
• CAS NO: 3810-35-3
• Molecular Formula: C₈H₅N₃O₃S₂
• Molecular Weight: 255.277
• EINECS: 223-282-9
• Mol File: 3810-35-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 255-256°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.675g/cm³
• Refractive Index: 1.752
• CAS DataBase Reference: tenonitrozole(CAS DataBase Reference)
• NIST Chemistry Reference: tenonitrozole(3810-35-3)
• EPA Substance Registry System: tenonitrozole(3810-35-3)

Safety Data

• Hazardous Substances Data: 3810-35-3(Hazardous Substances Data)

Usage

Originator

Tenonitrozole,Innotech

Manufacturing Process

To a solution of 1 kg (7 moles) of 2-amino-5-nitrothiazole in 5 L of pyridine (dried with potassium hydroxide) was added dropwise for 2-3 hours 8.5 moles of 2-thienoylchloride. N-(5-Nitro-2-thiazolyl)-2-thiophenecarboxamide was prepared as a yellow crystals with melting point 255-256°C.

Therapeutic Function

Antiprotozoal

InChI:InChI=1/C8H5N3O3S2/c12-7(5-2-1-3-15-5)10-8-9-4-6(16-8)11(13)14/h1-4H,(H,9,10,12)

Upstream product

• 5271-67-0 2-Thiophenecarbonyl chloride 
• 121-66-4 2-amino-5-nitro-1,3-thiazole 

Relevant articles and documents

Synthesis, in vitro bioassays, and computational study of heteroaryl nitazoxanide analogs

Antiprotozoal drug nitazoxanide (NTZ) has shown diverse pharmacological properties and has appeared in several clinical trials. Herein we present the synthesis, characterization, in vitro biological investigation, and in silico study of four hetero aryl amide analogs of NTZ. Among the synthesized molecules, compound 2 and compound 4 exhibited promising antibacterial activity against Escherichia coli (E. coli), superior to that displayed by the parent drug nitazoxanide as revealed from the in vitro antibacterial assay. Compound 2 displayed zone of inhibition of 20?mm, twice as large as the parent drug NTZ (10?mm) in their least concentration (12.5?μg/ml). Compound 1 also showed antibacterial effect similar to that of nitazoxanide. The analogs were also tested for in vitro cytotoxic activity by employing cell counting kit-8 (CCK-8) assay technique in HeLa cell line, and compound 2 was identified as a potential anticancer agent having IC50 value of 172?μg which proves it to be more potent than nitazoxanide (IC50?=?428?μg). Furthermore, the compounds were subjected to molecular docking study against various bacterial and cancer signaling proteins. The in vitro test results corroborated with the in silico docking study as compound 2 and compound 4 had comparatively stronger binding affinity against the proteins and showed a higher docking score than nitazoxanide toward human mitogen-activated protein kinase (MAPK9) and fatty acid biosynthesis enzyme (FabH) of E. coli. Moreover, the docking study demonstrated dihydrofolate reductase (DHFR) and thymidylate synthase (TS) as probable new targets for nitazoxanide and its synthetic analogs. Overall, the study suggests that nitazoxanide and its analogs can be a potential lead compound in the drug development.

Development of 5-nitrothiazole derivatives: Identification of leads against both replicative and latent Mycobacterium tuberculosis

Twenty eight 5-nitrothiazole derivatives were synthesized and evaluated for in vitro activities against Mycobacterium tuberculosis (MTB), cytotoxicity against HEK 293T. Among the compounds, 5-nitro-N-(5-nitrothiazol-2-yl)furan-2- carboxamide (20) was found to be the most active compound in vitro with MICs of 5.48 μM against log-phase culture of MTB and also non-toxic up to 100 μM.

Biological activity of modified and exchanged 2-amino-5-nitrothiazole amide analogues of nitazoxanide

Head group analogues of the antibacterial and antiparasitic drug nitazoxanide (NTZ) are presented. A library of 39 analogues was synthesized and assayed for their ability to suppress growth of Helicobacter pylori, Campylobacter jejuni, Clostridium difficile and inhibit NTZ target pyruvate:ferredoxin oxidoreductase (PFOR). Two head groups assayed recapitulated NTZ activity and possessed improved activity over their 2-amino-5-nitrothiazole counterparts, demonstrating that head group modification is a viable route for the synthesis of NTZ-related antibacterial analogues.