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Paper | Special issue | Vol 99, No. 2, 2019, pp.1032-1052
Published online, 19th December, 2018
DOI: 10.3987/COM-18-S(F)70
Synthesis and Evaluation of Topoisomerase I Inhibitors Possessing the 5,13-Dihydro-6H-benzo[6,7]indolo[3,2-c]quinolin-6-one Scaffold

Tsutomu Fukuda,* Yuri Matsuo, Fuyuki Matsuoka, Naoki Yoshioka, Gen Onodera, Masanari Kimura, Fumito Ishibashi, and Masatomo Iwao

*Division of Chemistry and Materials Science, Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan


Novel topoisomerase I inhibitors possessing the 5,13-dihydro- 6H-benzo[6,7]indolo[3,2-c]quinolin-6-one (BIQ) scaffold were designed and synthesized. This scaffold was constructed using sequential and regioselective functionalization of the pyrrole core through palladium-catalyzed cross-coupling, conventional electrophilic substitution, directed lithiation, and subsequent diphenylphosphoryl azide (DPPA)-mediated lactam ring construction. The obtained BIQs were evaluated for their topoisomerase I inhibitory activities and their antiproliferative activities in the panel of 39 human cancer cell lines established by the Japanese Foundation for Cancer Research (JFCR39).