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
收藏
页码：6885 / 6891
页数：7
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