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Preparation and antiplasmodial activity of 3',4'‐dihydro‐1' H ‐spiro(indoline‐3,2'‐quinolin)‐2‐ones
Author(s) -
Mathebula Bakolise,
Butsi Kamogelo Rosinah,
van Zyl Robyn Lynne,
Jansen van Vuuren Natasha Colleen,
Hoppe Heinrich Carl,
Michael Joseph Philip,
de Koning Charles Bernard,
Rousseau Amanda Louise
Publication year - 2019
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.13598
Subject(s) - isoeugenol , isatin , indoline , chemistry , pyran , stereochemistry , strain (injury) , organic chemistry , biology , eugenol , anatomy
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‐2 H ‐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‐2 H ‐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).