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

被引：47

作者：

Buarque, Camilla D. ^{[1
,2
]}

Militao, Gardenia C. G. ^{[3
]}

Lima, Daisy J. B. ^{[4
]}

Costa-Lotufo, Leticia V. ^{[4
]}

Pessoa, Claudia ^{[4
]}

de Moraes, Manoel Odorico ^{[4
]}

Cunha-, Edezio Ferreira, Jr. ^{[5
]}

Torres-Santos, Eduardo Caio ^{[5
]}

Netto, Chaquip D. ^{[1
,6
]}

Costa, Paulo R. R. ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Ctr Ciencias Saude, Nucleo Pesquisas Prod Nat, Lab Quim Bioorgan, BR-21941590 Rio De Janeiro, Brazil

[2] Pontificia Univ Catolica Rio de Janeiro, Dept Quim, BR-22435900 Gavea Rio De Janeiro, RJ, Brazil

[3] Univ Fed Pernambuco, Dept Fisiol & Farmacol, BR-50670901 Recife, PE, Brazil

[4] Univ Fed Ceara, Dept Fisiol & Farmacol, Fortaleza, Ceara, Brazil

[5] Fiocruz MS, Inst Oswaldo Cruz, Lab Bioquim Tripanosomatideos, BR-21040900 Rio De Janeiro, Brazil

[6] Univ Fed Rio de Janeiro, Inst Quim, Lab Quim Organ, BR-27930560 Rio De Janeiro, Brazil

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2011年 / 19卷 / 22期

关键词：

Aza-Heck; Oxa-Heck; Azaarylation; Pterocarpanquinone; Aza-pterocarpanquinone; Antineoplasic activity; Antileishmanial activity; BIOREDUCTIVE ALKYLATING-AGENTS; BETA-LAPACHONE DERIVATIVES; HUMAN LUNG-CELLS; TRYPANOCIDAL ACTIVITY; TRYPANOSOMA-CRUZI; EXPRESSION; NAPHTHOQUINONES; INHIBITION;

D O I：

10.1016/j.bmc.2011.09.025

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6885 / 6891

页数：7

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