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

  • Bioorg Med Chem. 2011 Nov 15;19(22):6885-91. doi: 10.1016/j.bmc.2011.09.025.
Camilla D Buarque  1 ,  Gardenia C G Militão ,  Daisy J B Lima ,  Leticia V Costa-Lotufo ,  Cláudia Pessoa ,  Manoel Odorico de Moraes ,  Edézio Ferreira Cunha-Junior ,  Eduardo Caio Torres-Santos ,  Chaquip D Netto ,  Paulo R R Costa
Affiliations
  • 1. Departamento de Química, Pontifícia Universidade Católica do Rio de Janeiro, Rio de Janeiro, RJ, Brazil.
PMID: 22000949 DOI: 10.1016/j.bmc.2011.09.025
Abstract

Pterocarpanquinones (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 culture. Compounds 1a, 1c and 8 showed the best selectivity index.