Ud Din Zia, Fill Taicia Pacheco, de Assis Francisco Favaro, Lazarin-Bidóia Danielle, Kaplum Vanessa, Garcia Francielle Pelegrin, Nakamura Celso Vataru, de Oliveira Kleber Thiago, Rodrigues-Filho Edson
LaBioMMi, Departamento de Química, Universidade Federal de São Carlos, CP 676, 13.565-905 São Carlos, SP, Brazil.
LAQBO, Departamento de Química, Universidade Federal de São Carlos, CP 676, 13.565-905 São Carlos, SP, Brazil.
Bioorg Med Chem. 2014 Feb 1;22(3):1121-7. doi: 10.1016/j.bmc.2013.12.020. Epub 2013 Dec 23.
In this work the synthesis and antiparasitical activity of new 1,5-diaryl-3-oxo-1,4-pentadienyl derivatives are described. First, compounds 1a, 1b, 1c and 1d were prepared by acid-catalyzed aldol reaction between 2-butanone and benzaldehyde, anisaldehyde, p-N,N-dimethylaminobenzaldehyde and p-nitrobenzaldehyde. Reacting each of the methyl ketones 1a, 1b, 1c and 1d with the p-substituted benzaldehydes under basic-catalyzed aldol reaction, we further prepared compounds 2a-2p. All twenty compounds were evaluated for antiproliferative activity, particularly for promastigote of Leishmania amazonensis and epimastigote of Trypanosoma cruzi. All compounds showed good activity while nitro compounds 2i and 2k showed inhibition activity at a few μM.
本文描述了新型1,5 - 二芳基 - 3 - 氧代 - 1,4 - 戊二烯基衍生物的合成及其抗寄生虫活性。首先，通过2 - 丁酮与苯甲醛、茴香醛、对 - N,N - 二甲基氨基苯甲醛和对 - 硝基苯甲醛之间的酸催化羟醛缩合反应制备化合物1a、1b、1c和1d。使甲基酮1a、1b、1c和1d中的每一种与对 - 取代苯甲醛在碱催化的羟醛缩合反应下反应，我们进一步制备了化合物2a - 2p。对所有二十种化合物进行了抗增殖活性评估，特别是针对亚马逊利什曼原虫的前鞭毛体和克氏锥虫的上鞭毛体。所有化合物均表现出良好的活性，而硝基化合物2i和2k在几微摩尔浓度下显示出抑制活性。
