C ring may be dispensable for β-carboline: Design, synthesis, and bioactivities evaluation of tryptophan analog derivatives based on the biosynthesis of β-carboline alkaloids

被引：18

作者：

Huang, Yuanqiong ^{[1
]}

Liu, Yongxian ^{[1
]}

Liu, Yuxiu ^{[1
]}

Song, Hongjian ^{[1
]}

Wang, Qingmin ^{[1
]}

机构：

[1] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2016年 / 24卷 / 03期

基金：

中国国家自然科学基金;

关键词：

beta-Carboline; Tryptophan; Biosynthesis; Anti-TMV; Fungicide; BIOLOGICAL-ACTIVITIES; PATHWAY;

D O I：

10.1016/j.bmc.2015.08.016

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：

According to our previous work and the latest research on the biosynthesis of beta-carboline, and using the reverse thinking strategy, tryptophan, the biosynthesis precursor of beta-carboline alkaloids, and their derivatives were synthesized, and their biological activities and structure-activity relationships were studied. This bioassay showed that these compounds exhibited good inhibitory activities against tobacco mosaic virus (TMV); especially (S)-2-amino-3-(1H-indol-3-yl)-N-octylpropanamide (4) (63.3 +/- 2.1%, 67.1 +/- 1.9%, 68.7 +/- 1.3%, and 64.5 +/- 3.1%, 500 mu g/mL) exhibited the best antiviral activity both in vitro and in vivo. Compound 4 was chosen for the field trials and the acute oral toxicity test, the results showed that the compound exhibited good anti-TMV activity in the field and low acute oral toxicity. We also found that these compounds showed antifungal activities and insecticidal activities. (C) 2016 Published by Elsevier Ltd.

引用

页码：462 / 473

页数：12