Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2- diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives

Authors

Lidia Matesic, University of WollongongFollow
Julie M. Locke, University of WollongongFollow
Kara Vine, University of WollongongFollow
Marie Ranson, University of WollongongFollow
John B. Bremner, University of WollongongFollow
Danielle Skropeta, University of WollongongFollow

RIS ID

61351

Publication Details

Matesic, L., Locke, J. M.., Vine, K., Ranson, M., Bremner, J. B. & Skropeta, D. (2012). Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2- diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives. Tetrahedron, 68 (34), 6810-6819.

Abstract

To further expand the structure–cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 μM) after 24 h.