98591-60-7

Usage

InChI:InChI=1/C9H5ClN2O2/c10-7(13)9-12-11-8(14-9)6-4-2-1-3-5-6/h1-5H

Upstream product

• 79-37-8 oxalyl dichloride 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 
• 99066-76-9 5-phenyl-1,3,4-oxadiazole-2-carboxylic acid 
• 16691-25-1 ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate 
• 60214-04-2 ethyl 2-(2-benzoylhydrazineyl)-2-oxoacetate 
• 613-94-5 benzoic acid hydrazide 

Downstream Products

• 16691-26-2 methyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate 
• 927671-80-5 5-phenyl-[1,3,4]oxadiazole-2-carboxylic acid [2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-methylamide 

Relevant academic research and scientific papers

Discovery of Novel Aryl Carboxamide Derivatives as Hypoxia-Inducible Factor 1α Signaling Inhibitors with Potent Activities of Anticancer Metastasis

In order to discover novel hypoxia-inducible factor 1 (HIF-1) inhibitors for the cancer metastasis treatment, 68 new aryl carboxamide compounds were synthesized and evaluated for their inhibitory effect by dual luciferase-reporter assay. Based on five rounds of investigation on structure-activity relationships step by step, compound 30m was discovered as the most active inhibitor (IC50 = 0.32 μM) with no obvious cytotoxicity (CC50 > 50 μM). It effectively attenuated hypoxia-induced HIF-1α protein accumulation and reduced transcription of vascular epidermal growth factor in a dose-dependent manner, which was further demonstrated by its inhibitory potency on capillary-like tube formation, angiogenesis of zebrafish as well as cellular migration and invasion. Importantly, compound 30m exhibited antimetastatic potency in breast cancer lung metastasis in the mice model, indicating its promising therapeutic potential for prevention and treatment of tumor metastasis. These results definitely merit attention for further rational design of more efficient HIF-1 inhibitors in the future.

Intramolecular cycloadditions of photogenerated azaxylylenes with oxadiazoles provide direct access to versatile polyheterocyclic ketopiperazines containing a spiro-oxirane moiety

Photogenerated azaxylylenes undergo intramolecular cycloadditions to 1,3,4-oxadiazole pendants, which are accompanied by concomitant release of dinitrogen, yielding functionalized ketopiperazinoquinolinols containing an oxirane moiety fused to the quinolinole moiety while spiro-connected to diketopiperazine. These primary photoproducts are reactive versatile intermediates which can be further derivatized under nucleophilic SN1- or SN2-like ring opening of the oxirane moiety. The oxidized quinolinones undergo new rearrangements under the conditions of the Schmidt reaction, leading to unprecedented triazacanoindolinones.

Synthesis, enzyme kinetics and computational evaluation of N-(β-d-glucopyranosyl) oxadiazolecarboxamides as glycogen phosphorylase inhibitors

All possible isomers of N-β-d-glucopyranosyl aryl-substituted oxadiazolecarboxamides were synthesised. O-Peracetylated N-cyanocarbonyl-β- d-glucopyranosylamine was transformed into the corresponding N-glucosyl tetrazole-5-carboxamide, which upon acylation