4882-92-2Relevant academic research and scientific papers
Design, synthesis and biological evaluation of new Axl kinase inhibitors containing 1,3,4-oxadiazole acetamide moiety as novel linker
Xu, Congjun,Han, Yufei,Xu, Sicong,Wang, Ruxin,Yue, Ming,Tian, Yu,Li, Xiaofan,Zhao, Yanfang,Gong, Ping
, (2019/12/09)
Using the principle of bioisosteric replacement, we present a structure-based design approach to obtain new Axl kinase inhibitors with significant activity at the kinase and cellular levels. Through a stepwise structure-activity relationships exploration, a series of 6,7-disubstituted quinoline derivatives, which contain 1,3,4-oxadiazol acetamide moiety as novel Linker, were ultimately synthesized with Axl as the primary target. Most of them exhibited moderate to excellent activity, with IC50 values ranging from 0.032 to 1.54 μM against the tested cell lines. Among them, the most promising compound 47e, as an Axl kinase inhibitor (IC50 = 10 nM), shows remarkable cytotoxicity against A549, HT-29, PC-3, MCF-7, H1975 and MDA-MB-231 cell lines. More importantly, 47e also shows a significant inhibitory effect on EGFR-TKI resistant NSCLC cell lines H1975/gefitinib. Meanwhile, this study provides a novel type of linker for Axl kinase inhibitors, namely 1,3,4-oxadiazol acetamide moiety, which is out of the scope of the “5- atoms role ".
Polynuclear nonfused tetrazole-, 1,3,4-oxadiazole-, and 1,2,3-triazole-containing systems
Vereshchagin,Petrov,Proidakov,Pokatilov,Smirnov,Kizhnyaev
, p. 912 - 917 (2007/10/03)
Polynuclear nonfused blocks containing 1,2,3-triazole, 1,3,4-oxadiazole, and tetrazole rings were synthesized by reaction of C-substituted tetrazoles with carboxylic acid chlorides, as well as by cycloaddition of 2-azidomethyl-1,3,4-oxadiazoles at the triple bond of acetylenic compounds. Pleiades Publishing, Inc., 2006.
Synthesis of 5-aryl-1,3,4-oxadiazolyl-2-acetic acids
Janda, Lubomir
, p. 411 - 416 (2007/10/03)
Ethyl (1H-tetrazol-5-yl)acetate is acylated with aroyl chlorides and heteroaroyl chlorides in pyridine. The intermediate acyltetrazoles undergo thermal degradation to ethyl (5-aryl-1,3,4-oxadiazol-2-yl)acetates and (5-heteroaryl-1,3,4-oxadiazol-2-yl)acetates, respectively, in good yields. The corresponding acetic acids are obtained by potassium hydroxide mediated hydrolysis of the esters in anhydrous ethanol.
STUDIES ON ALKYLHETEROAROMATIC COMPOUNDS: NEW SYNTHESES OF 1,3,4-OXADIAZOLE, OXADIAZOLOPYRIDINE, 1,3,4-THIADIAZOLE, THIADIAZOLOPYRIDINE, PHTHALAZINE AND THIENOPYRIDAZINE DERIVATIVES.
Elnagdi, Mohamed Hilmy,Erian, Ayman Wahba,Sadek, Kamal Usef,Selim, Maghraby Ali
, p. 1124 - 1142 (2007/10/02)
Ethyl 5-phenyl-1,3,4-oxadiazol-2-ylacetate (3a) could be prepared via condensation of ethyl 3-amino-3-ethoxyprop-2-enoate (1) with benzoylhydrazine.This product coupled with aromatic diazonium salts to yield arylhydrazones 4a,b.Compound 3a was converted i
