Pterocarpanquinones, aza-pterocarpanquinone and derivatives: Synthesis, antineoplasic activity on human malignant cell lines and antileishmanial activity on Leishmania amazonensis

Buarque, Camilla D.
Militão, Gardenia C.G.
Lima, Daisy J.B.
Costa-Lotufo, Leticia V.
Pessoa, Cláudia
de Moraes, Manoel Odorico
Cunha-Junior, Edézio Ferreira
Torres-Santos, Eduardo Caio
Netto, Chaquip D.
Costa, Paulo R.R.

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Publication date

November 2011

DOI

10.1016/j.bmc.2011.09.025

Publisher

Elsevier Ltd.

ISSN

0968-0896

Citation count (estimate)

Abstract

AbstractPterocarpanquinones (1a–e) and the aza-pterocarpanquinone (2) were synthesized through palladium catalyzed oxyarylation and azaarylation of conjugate olefins, and showed antineoplasic effect on leukemic cell lines (K562 and HL-60) as well as colon cancer (HCT-8), gliobastoma (SF-295) and melanoma (MDA-MB435) cell lines. Some derivatives were prepared (3–8) and evaluated, allowing establishing the structural requirements for the antineoplasic activity in each series. Compound 1a showed the best selectivity index in special for leukemic cells while 2 showed to be more bioselective for HCT-8, SF-295 and MDA-MB435 cells. Pterocarpanquinones 1a and 1c–e, as well as 8 were the most active on amastigote form of Leishmania amazonensis in cu...