Ultrasound-assisted-one-pot synthesis and antiplasmodium evaluation of 3-substituted-isoindolin-1-ones

As the attempts to control malaria through chemotherapy strategies are restricted, we have prepared a small library of 3-substituted-isoindolinones from ( Z )-3-benzylideneisobenzofuran-1(3 H )-ones in one-pot fashion under ultrasound irradiation. The one-pot reaction was scalable and efficiently pr...

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Bibliographic Details
Published in:RSC advances 2023-09, Vol.13 (37), p.25959-25967
Main Authors: Mardjan, Muhammad Idham Darussalam, Hariadi, Muhamad Fadhly, Mustika, Chessy Rima, Saifurofi', Hamzah Shiddiq, Kunarti, Eko Sri, Purwono, Bambang, Commeiras, Laurent
Format: Article
Language:English
Subjects:
Chemical Sciences
Chemistry
Low resistance
Malaria
Organic chemistry
Substitutes
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Summary:As the attempts to control malaria through chemotherapy strategies are restricted, we have prepared a small library of 3-substituted-isoindolinones from ( Z )-3-benzylideneisobenzofuran-1(3 H )-ones in one-pot fashion under ultrasound irradiation. The one-pot reaction was scalable and efficiently produced the desired products ( 1a-m ) in high yields in a short reaction time. Evaluation of their in vitro antiplasmodium assay against the 3D7 (chloroquine-sensitive) and FCR3 (chloroquine-resistant) strains of Plasmodium falciparum demonstrated that they displayed moderate to strong antiplasmodium activities (the IC 50 values ranging from 4.21-34.80 μM) and low resistance indices. The in silico prediction of ADME and physicochemical properties showed that the synthesized compounds met the drug-likeliness requirements and featured low toxicity effects. Based on the evaluation of the antiplasmodium profiles, 3-substituted-isoindolinone derivatives of 1a , 1d , 1h , and 1l may become potential antiplasmodium candidates. A library of 3-substituted-isoindolin-1-ones has been synthesized from 3-alkylidenephtalides and primary amines through one-pot reaction under ultrasonic irradiation. Four isoindolin-1-ones have great potential to be antiplasmodium candidates.
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra02829a