Synthesis and Antitrypanosomastid Activity of 1,4-Diaryl-1,2,3-triazole Analogues of Neolignans Veraguensin, Grandisin and Machilin G

被引：29

作者：

Cassamale, Tatiana B. ^{[1
]}

Costa, Eduarda C. ^{[1
]}

Carvalho, Diego B. ^{[1
]}

Cassemiro, Nadla S. ^{[1
]}

Tomazela, Carolina C. ^{[2
]}

Marques, Maria C. S. ^{[2
]}

Ojeda, Mariah ^{[3
]}

Matos, Maria F. C. ^{[3
]}

Albuquerque, Sergio ^{[4
]}

Arruda, Carla C. P. ^{[2
]}

Baroni, Adriano C. M. ^{[1
]}

机构：

[1] Univ Fed Mato Grosso do Sul, Ctr Ciencias Biol & Saude, Lab Sintese & Quim Med LASQUIM, BR-79070900 Campo Grande, MS, Brazil

[2] Univ Fed Mato Grosso do Sul, Ctr Ciencias Biol & Saude, Lab Parasitol Humana, BR-79070900 Campo Grande, MS, Brazil

[3] Univ Fed Mato Grosso do Sul, Ctr Ciencias Biol & Saude, Lab Biol Mol & Culturas Celulares, BR-79070900 Campo Grande, MS, Brazil

[4] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Anal Clin Toxicol & Bromatol, BR-14040930 Ribeirao Preto, SP, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2016年 / 27卷 / 07期

关键词：

1,4-diaryl-1,2,3-triazole derivative; tetrahydrofuran neolignan; click chemistry; antitrypanosomatid activity; VISCERAL LEISHMANIASIS; CYTOTOXICITY; 1,2,3-TRIAZOLE; PAROMOMYCIN; CONVERSION; SYSTEM; DRUGS; ARYL;

D O I：

10.5935/0103-5053.20160017

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sixteen 1,4-diaryl-1,2,3-triazole compounds derived from the natural products veraguensin, grandisin and machilin G were synthesized, with yields of 78-92%. Biological activity tests against Leishmania amazonensis promastigotes showed that three of these compounds were the most active, with maximum inhibitory concentration (IC50) values of 1.1, 3.71 and 7.23 mu M. One compound was highly active against Leishmania infantum, with an IC50 value of 5.2 mu M, and one derivative showed an IC50 value of 28.6 mu M against Trypanosoma cruzi trypomastigotes. Regarding structure-activity relationship (SAR), hybrid 1,2,3-triazolic compounds containing a methylenedioxy group, showed the best antileishmanial and antitrypanosomal activities.

引用

页码：1217 / 1228

页数：12

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