Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a redox-amination–aromatization–Friedel–Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors

Shanchao Wu; Na Liu; Guoqiang Dong; Lin Ma; Shengzheng Wang; Wencai Shi; Kun Fang; Shuqiang Chen; Jian Li; Wannian Zhang; Chunquan Sheng; Wei Wang

doi:10.1039/C6CC03071H

Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a redox-amination–aromatization–Friedel–Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors†

Shanchao Wu,‡^a Na Liu,‡^a Guoqiang Dong,‡^a Lin Ma,^a Shengzheng Wang,^a Wencai Shi,^b Kun Fang,^ac Shuqiang Chen,^a Jian Li,^c Wannian Zhang,*^a Chunquan Sheng*^a and Wei Wang*^cd

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* Corresponding authors

^a Department of Medicinal Chemistry, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, P. R. China
E-mail: shengcq@hotmail.com, zhangwnk@hotmail.com

^b Department of Clinical Nutrition, Changhai Hospital, Second Military Medical University, 168 Changhai Road, Shanghai 200433, P. R. China

^c School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. China

^d Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, USA
E-mail: wwang@unm.edu

Abstract

An efficient redox-amination–aromatization–Friedel–Crafts acylation cascade process from trans-4-hydroxyproline and 2-formylbenzoic acids has been developed for the synthesis of pyrrolo[1,2-b]isoquinolin-10(5H)-ones. Compound 3h was identified as a new potent dual topoisomerase I/II inhibitor.

Chemical Communications

Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a redox-amination–aromatization–Friedel–Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors†

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Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a redox-amination–aromatization–Friedel–Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors

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