64398-84-1

Basic information

• Product Name: N-(5-nitro-2-thiazolyl)benzamide
• Synonyms: N-(5-nitro-2-thiazolyl)benzamide;benzamido-2-nitro-5-thiazole;N-(5-nitro-1,3-thiazol-2-yl)benzamide
• CAS NO: 64398-84-1
• Molecular Formula: C₁₀H₇N₃O₃S
• Molecular Weight: 249.24588
• EINECS: 264-868-4
• Mol File: 64398-84-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 1.53g/cm³
• Refractive Index: 1.713
• CAS DataBase Reference: N-(5-nitro-2-thiazolyl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5-nitro-2-thiazolyl)benzamide(64398-84-1)
• EPA Substance Registry System: N-(5-nitro-2-thiazolyl)benzamide(64398-84-1)

Safety Data

• Hazardous Substances Data: 64398-84-1(Hazardous Substances Data)

Usage

General Description

N-(5-nitro-2-thiazolyl)benzamide is a chemical compound with the molecular formula C9H6N4O3S. It is a derivative of benzamide and contains a nitrothiazole group. N-(5-nitro-2-thiazolyl)benzamide has applications in medicinal chemistry as it exhibits antiparasitic activity. It has been studied as a potential drug candidate for the treatment of malaria and trypanosomiasis. N-(5-nitro-2-thiazolyl)benzamide may also have other biological activities and could serve as a lead compound for the development of new pharmaceuticals. Its structure and properties make it a subject of interest for further research in the field of drug discovery and development.

InChI:InChI=1/C10H7N3O3S/c14-9(7-4-2-1-3-5-7)12-10-11-6-8(17-10)13(15)16/h1-6H,(H,11,12,14)

Upstream product

• 121-66-4 2-amino-5-nitro-1,3-thiazole 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 

Downstream Products

• 38922-45-1 N-(5-nitro-thiazol-2-yl)-N-propionyl-glycine ethyl ester 
• 38922-31-5 2-(2-benzoylimino-5-nitro-thiazol-3-yl)-N,N-dimethyl-acetamide 
• 38922-49-5 2-(2-benzoylimino-5-nitro-thiazol-3-yl)-N,N-dipropyl-acetamide 

Relevant articles and documents

Structure-Activity Study of Nitazoxanide Derivatives as Novel STAT3 Pathway Inhibitors

We identified nitazoxanide (NTZ) as a moderate STAT3 pathway inhibitor through immunoblot analysis and a cell-based IL-6/JAK/STAT3 pathway activation assay. A series of thiazolide derivatives were designed and synthesized to further validate the thiazolide scaffold as STAT3 inhibitors. Eight out of 25 derivatives displayed potencies greater than that of NTZ, and their STAT3 pathway inhibitory activities were found to be significantly correlated with their antiproliferative activities in HeLa cells. Derivatives 15 and 24 were observed to be more potent than the positive control WP1066, which is under phase I clinical trials. Compared with NTZ, 15 also exhibited much improved in vivo pharmacokinetic parameters in rats and efficacies against proliferations in multiple cancer cell lines, indicating a broad-spectrum effect of these thiazolides as antitumor agents targeted on STAT3.

2-Acylamino-5-nitro-1,3-thiazoles: Preparation and in vitro bioevaluation against four neglected protozoan parasites

The 2-acylamino-5-nitro-1,3-thiazole derivatives (1-14) were prepared using a one step reaction. All compounds were tested in vitro against four neglected protozoan parasites (Giardia intestinalis, Trichomonas vaginalis, Leishmania amazonensis and Trypanosoma cruzi). Acetamide (9), valeroylamide (10), benzamide (12), methylcarbamate (13) and ethyloxamate (14) derivatives were the most active compounds against G. intestinalis and T. vaginalis, showing nanomolar inhibition. Compound 13 (IC50 = 10 nM), was 536-times more active than metronidazole, and 121-fold more effective than nitazoxanide against G. intestinalis. Compound 14 was 29-times more active than metronidazole and 6.5-fold more potent than nitazoxanide against T. vaginalis. Ureic derivatives 2, 3 and 5 showed moderate activity against L. amazonensis. None of them were active against T. cruzi. Ligand efficiency indexes analysis revealed higher intrinsic quality of the most active 2-acylamino derivatives than nitazoxanide and metronidazole. In silico toxicity profile was also computed for the most active compounds. A very low in vitro mammalian cytotoxicity was obtained for 13 and 14, showing selectivity indexes (SI) of 246,300 and 141,500, respectively. Nitazoxanide showed an excellent leishmanicidal and trypanocidal effect, repurposing this drug as potential new antikinetoplastid parasite compound.

Research on nitro-derivatives of biological interest. XVI. Structure-activity relationships as protozoocidal, anthelmintic and molluscicidal agents in 2-benzamido 5-nitrothiazole series

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