82380-66-3Relevant academic research and scientific papers
Design, synthesis and evaluation of new bioactive oxadiazole derivatives as anticancer agents targeting bcl-2
Hamdy, Rania,Elseginy, Samia A.,Ziedan, Noha I.,El-Sadek, Mohamed,Lashin, Elsaid,Jones, Arwyn T.,Westwell, Andrew D.
, p. 1 - 11 (2020/12/01)
A series of 2-(1H-indol-3-yl)-5-substituted-1,3,4-oxadiazoles, 4a–m, were designed, synthesized and tested in vitro as potential pro-apoptotic Bcl-2 inhibitory anticancer agents based on our previously reported hit compounds. Synthesis of the target 1,3,4-oxadiazoles was readily accomplished through a cyclization reaction of indole carboxylic acid hydrazide 2 with substituted carboxylic acid derivatives 3a–m in the presence of phosphorus oxychloride. New compounds 4a–m showed a range of IC50 values concentrated in the low micromolar range selectively in Bcl-2 positive human cancer cell lines. The most potent candidate 4-trifluoromethyl substituted analogue 4j showed selective IC50 values of 0.52–0.88 μM against Bcl-2 expressing cell lines with no inhibitory effects in the Bcl-2 negative cell line. Moreover, 4j showed binding that was two-fold more potent than the positive control gossypol in the Bcl-2 ELISA binding affinity assay. Molecular modeling studies helped to further rationalize anti-apoptotic Bcl-2 binding and identified compound 4j as a candidate with drug-like properties for further investigation as a selective Bcl-2 inhibitory anticancer agent.
Discovery of Pimprinine Alkaloids as Novel Agents against a Plant Virus
Liu, Bin,Li, Rui,Li, Yanan,Li, Songyi,Yu, Jin,Zhao, Binfen,Liao, Ancai,Wang, Ying,Wang, Ziwen,Lu, Aidang,Liu, Yuxiu,Wang, Qingmin
, p. 1795 - 1806 (2019/02/27)
Plant viral diseases cause tremendous decreases in crop yield and quality. Natural products have always been a valuable source for lead discovery in medicinal and agricultural chemistry. A series of pimprinine alkaloids and their derivatives were prepared and identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HR-MS). The antiviral activities of these alkaloids against tobacco mosaic virus (TMV) were systematically investigated for the first time. Most of the compounds exhibited higher antiviral activities than ribavirin. Compounds 5l, 9h, and 10h, which had similar or higher antiviral activities than ningnanmycin (perhaps the most widely used antiviral agent at present), emerged as new antiviral pilot compounds. This systematic structure-activity-relationship research lays the foundation for simplifying the structure of these alkaloids. The ring-open products, acylhydrazones 9a-9u, were also found to possess good antiviral activities. Moreover, all the synthesized compounds displayed broad-spectrum fungicidal activities. This study provides important information for the research and development of pimprinine alkaloids as novel antiviral agents.
Synthesis and properties of azoles and their derivatives. 33. Synthesis of 1,3,4-oxadiazoles that contain an indolyl group
Kelarev,Shvekhgeimer
, p. 258 - 261 (2007/10/02)
2,5-Disubstituted oxadiazoles with indole residues were synthesized by condensation of the hydrochlorides of the corresponding imido esters with hydrazines, as well as by cyclization of hydrazides by the action of POCl3. 2-Substituted oxadiazoles of the same series were obtained by condensation of the corresponding hydrazides with ethyl orthoformate.
