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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

Journal Article


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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.

Publication Date


  • 2012

Citation


  • 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.

Scopus Eid


  • 2-s2.0-84863629464

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=8086&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4743

Number Of Pages


  • 9

Start Page


  • 6810

End Page


  • 6819

Volume


  • 68

Issue


  • 34

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.

Publication Date


  • 2012

Citation


  • 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.

Scopus Eid


  • 2-s2.0-84863629464

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=8086&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/4743

Number Of Pages


  • 9

Start Page


  • 6810

End Page


  • 6819

Volume


  • 68

Issue


  • 34