Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones.,Chemical Biology & Drug Design

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Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones.
Chemical Biology & Drug Design ( IF 3.2 ) Pub Date : 2019-08-27 , DOI: 10.1111/cbdd.13598
Bakolise Mathebula ₁ , Kamogelo Rosinah Butsi _{1,

2} , Robyn Lynne van Zyl _{2,

3} , Natasha Colleen Jansen van Vuuren _{2,

3} , Heinrich Carl Hoppe ₄ , Joseph Philip Michael ₁ , Charles Bernard de Koning ₁ , Amanda Louise Rousseau _{1,

2}

Affiliation

A series of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones were prepared by the inverse-electron-demand aza-Diels-Alder reaction (Povarov reaction) of imines derived from isatin and substituted anilines, and the electron-rich alkenes trans-isoeugenol and 3,4-dihydro-2H-pyran. These compounds were assessed for in vitro antiplasmodial activity against drug-sensitive and drug-resistant forms of the P. falciparum parasite. Three compounds derived from 3,4-dihydro-2H-pyran and four compounds derived from trans-isoeugenol showed antiplasmodial activity in the low micromolar range against the drug-resistant FCR-3 strain (1.52-4.20 µM). Only compounds derived from trans-isoeugenol showed antiplasmodial activity against the drug-sensitive 3D7 strain (1.31-1.80 µM).

中文翻译：

3'，4'-二氢-1'H-螺（吲哚啉-3,2'-喹啉）-2-酮的制备及其抗血浆活性。

通过反电子需求的氮杂-Diels-Alder反应（Povarov反应）制备了一系列的3'，4'-二氢-1'H-螺（吲哚啉-3,2'-喹啉）-2-酮。亚胺衍生自Isatin和取代的苯胺，以及富含电子的烯烃反式异丁香酚和3,4-二氢-2H-吡喃。评估了这些化合物对恶性疟原虫寄生虫的药物敏感性和耐药性形式的体外抗血浆活性。衍生自3,4-二氢-2H-吡喃的三种化合物和衍生自反异丁香酚的四种化合物在低微摩尔范围内对耐药FCR-3菌株（1.52-4.20 µM）表现出抗血浆活性。仅衍生自反式异丁香酚的化合物显示出对药物敏感的3D7菌株（1.31-1.80 µM）的抗血浆活性。

更新日期：2019-08-27

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