Exploration of Pd-catalysed four-component tandem reaction for one-pot assembly of pyrazolo[1,5-c]quinazolines as potential EGFR inhibitors.

钯催化四组分串联反应一锅法构建吡唑并[1,5-c]喹唑啉类潜在EGFR抑制剂的探索

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ID: 58786
2019
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Abstract
A series of pyrazolo[1,5-c]quinazolines as EGFR inhibitors was designed and synthesized by highly efficient and novel multicomponent route involving Pd-catalyzed tandem one-pot four-component reaction. The reaction proceeds with good functional group tolerance under a simple condition with excellent regioselectivity and high efficiency. Target compounds were screened against cancer cell lines MDA-MB-231, A549 and H1299. Of these, 9b and 10b exhibited superior anticancer activity (IC < 2.5 μM) to erlotinib and gefitinib. Synthetics were able to inhibit EGFR mediated kinase activity, induced ROS in cancer cells promoting mitochondrial mediated apoptosis via halting cell cycle progression at G1 phase.
本研究通过涉及钯催化串联一锅法四组分反应的高效新颖多组分路线，设计并合成了一系列作为EGFR抑制剂的吡唑并[1,5-c]喹唑啉类化合物。该反应在简便的条件下进行，具有良好的官能团耐受性、优异的区域选择性和高效率。针对癌细胞系MDA-MB-231、A549和H1299对目标化合物进行了抗肿瘤活性筛选。其中，9b和10b表现出优于厄洛替尼和吉非替尼的抗癌活性（IC < 2.5 μM）。这些合成化合物能够抑制EGFR介导的激酶活性，诱导癌细胞内活性氧（ROS）产生，并通过将细胞周期阻滞于G1期来促进线粒体介导的细胞凋亡。
Reference Key
ansari2019explorationbioorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Ansari, Arshad J;Joshi, Gaurav;Yadav, Umesh Prasad;Maurya, Antim K;Agnihotri, Vijai K;Kalra, Sourav;Kumar, Raj;Singh, Sandeep;Sawant, Devesh M;
Journal Bioorganic chemistry
Year 2019
DOI
S0045-2068(19)30785-0
URL
Keywords
catalysis EGFR anticancer molecular modelling drug discovery pyrazolo[1,5-c]quinazolines

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