Synthesis and biological evaluation of 4,5,6,7‐tetrahydrothieno[2,3‐c]pyridine–based β‐aminonitriles and their derivatives: β‐amino carboxamides, (thio)ureas, and tetracycles,Journal of Heterocyclic Chemistry

当前位置： X-MOL 学术 › J. Heterocycl. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis and biological evaluation of 4,5,6,7‐tetrahydrothieno[2,3‐c]pyridine–based β‐aminonitriles and their derivatives: β‐amino carboxamides, (thio)ureas, and tetracycles
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2019-12-23 , DOI: 10.1002/jhet.3800
Ramóna Madácsi _{1,

2} , Péter Traj ₂ , László Hackler ₁ , Lajos I. Nagy ₁ , Beáta Kari ₁ , László G. Puskás ₁ , Iván Kanizsai ₁

Affiliation

The preparation and cytotoxic characterization of 4,5,6,7‐tetrahydrothieno[2,3‐c]pyridine–based β‐aminonitriles, β‐amino carboxamides, and their (thio)urea and annulated derivatives were accomplished. Following a synthetic route involving Gewald three‐component reactions (G‐3CR) and a Lewis acid–catalyzed iso (thio)cyanate coupling, 30 compounds were prepared for antitumor evaluation. For derivatizations, a catalytic amount of CuOAc₂ (20 mol%) was essential for improving the reactivity of either the C‐2 amino function of thiophene or isocyanates. The synthesized analogues demonstrated a weak to moderate antitumor activity in a low micromolar range against A549 and K562 cancer cell lines.

中文翻译：

4,5,6,7-四氢噻吩并[2,3-c]吡啶基β-氨基腈及其衍生物：β-氨基羧酰胺，（硫）脲和四环化合物的合成和生物学评估

完成了4,5,6,7-四氢噻吩并[2,3- c ]吡啶基的β-氨基腈，β-氨基羧酰胺及其（硫代）尿素和环状衍生物的制备和细胞毒性表征。按照涉及Gewald三组分反应（G-3CR）和路易斯酸催化的异（硫）氰酸酯偶联的合成路线，制备了30种化合物用于抗肿瘤评估。对于衍生化，催化量的CuOAc ₂（20 mol％）对于提高噻吩或异氰酸酯的C-2氨基官能团的反应性至关重要。合成的类似物在低微摩尔范围内显示出对A549和K562癌细胞系的弱至中度抗肿瘤活性。

更新日期：2019-12-23

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11