通过 Pd 催化叔丁基异腈与硫代酰胺的双环化反应合成咪唑并[1,2-c]噻唑。

Synthesis of imidazo[1,2-c]thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides.

机构信息

State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences of Guangxi Normal University, Guilin 541004, People's Republic of China and School of Pharmaceutical Science, Gannan Medical University, Ganzhou, Jiangxi 341000, P. R. China.

出版信息

Org Biomol Chem. 2019 Sep 28;17(36):8403-8407. doi: 10.1039/c9ob01664c. Epub 2019 Sep 4.

DOI:10.1039/c9ob01664c

PMID:31482915

Abstract

Building new biological molecules is challenging. Herein, imidazo[1,2-c]thiazoles were synthesized as a new class of heterobicyclic analogs through Pd-catalyzed cascade bicyclization from isonitriles with thioamides. The bicyclic scaffolds were constructed by inserting three molecules of isonitrile into two molecules of thioamide and then cyclizing them in a one-pot procedure. In vitro antitumor studies of these new compounds were conducted by using the MTT assay, and compound 3c showed excellent inhibitory effects against HepG2 at 7.06 ± 0.68 μM.

摘要

构建新的生物分子具有挑战性。在此，通过 Pd 催化的从异腈与硫代酰胺的级联双环化反应，合成了咪唑并[1,2-c]噻唑作为一类新的杂双环类似物。双环骨架是通过将三个异腈分子插入两个硫代酰胺分子中，然后在一锅法中进行环化构建的。通过 MTT 测定法对这些新化合物进行了体外抗肿瘤研究，化合物 3c 在 7.06 ± 0.68 μM 时对 HepG2 显示出优异的抑制作用。