Synthesis of Isobenzofuranones and Isoindolinones via Claisen–Schmidt Condensation and Their Antileishmanial Activity
In this study, we describe the synthesis of isobenzofuranones and isoindolinones using the Claisen-Schmidt condensation via the formation of a chalcone intermediate, followed by a 5-<i>exo</i>-<i>trig</i> cyclization facilitated by the carboxylate group under basic conditions. The desired products were obtained in good yields. Subsequently, Michael-lactamization reaction of the isobenzofuranones was employed to synthesize isoindolinone derivatives. The three-component Mannich-lactamization reaction was also explored to synthesize isoindolinones from 2-hydroxyacetophenone, phthalaldehydic acid, and amine derivatives. Furthermore, the synthesized compound <b>5c</b> exhibited low EC<sub>50</sub> (μM) values against <i>Leishmania donovani</i> (<i>L. donovani</i>), with no significant cytotoxicity observed against L-6 cells.
Authors
- George W. Weaver (ORCID: https://orcid.org/0000-0002-1316-1941)
- Avninder S. Bhambra (ORCID: https://orcid.org/0000-0001-7673-4797)
- Nattanit Suddee
- Chatphorn Theppitak (ORCID: https://orcid.org/0000-0003-2091-4937)
- Annie E. Taylor (ORCID: https://orcid.org/0000-0003-3381-592X)
- Randolph Arroo (ORCID: https://orcid.org/0000-0002-0672-7927)
- Marcel Kaiser (ORCID: https://orcid.org/0000-0003-1785-7302)
- S Ruchirawat
- Pascal Maeser
- Sireethon Khotsombat
- Nopporn Thasana
Institutions
- Ministry of Higher Education (MY)
- Loughborough University (GB)
- Swiss Tropical and Public Health Institute (CH)
- Chulabhorn Graduate Institute (TH)
- Leicester College (GB)
- Chulabhorn Research Institute (TH)
- Ministry of Higher Education (CM)
- NOAA Chemical Sciences Laboratory (US)
- Medicina (PL)
- De Montfort University (GB)
Publication Details
- Journal
- ACS Omega
- Published
- 2026-01-20
- DOI
- https://doi.org/10.1021/acsomega.5c08000
- Primary Topic
- Synthesis and pharmacology of benzodiazepine derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00