64398-84-1

Usage

Uses

Used in Pharmaceutical Industry:
N-(5-nitro-2-thiazolyl)benzamide is used as a potential drug candidate for the treatment of parasitic diseases such as malaria and trypanosomiasis. Its antiparasitic activity makes it a valuable asset in the development of new treatments for these life-threatening conditions.
Used in Drug Discovery and Development:
N-(5-nitro-2-thiazolyl)benzamide serves as a lead compound for the development of new pharmaceuticals. Its unique structure and properties make it a subject of interest for researchers in the field of drug discovery and development. Further studies on N-(5-nitro-2-thiazolyl)benzamide may lead to the identification of novel therapeutic agents with improved efficacy and safety profiles.

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

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

Downstream Products

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

Relevant academic research and scientific papers

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.

MODIFIED PROTEINS AND PROTEIN DEGRADERS

Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.

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.

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.