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- Title
Synthesis, cytotoxicity, and antibacterial studies of 2,4,5,6‐substituted hexahydro‐1H‐isoindole‐1,3(2H)‐dione.
- Authors
Yetişkin, Egehan; Gündoğdu, Özlem; Mete, Derya; Çelebioğlu, Neslihan; Kara, Yunus; Şanlı‐Mohamed, Gülşah
- Abstract
In this study, synthesis of novel isoindole‐1,3‐dione analogues bearig halo, hydroxy, and acetoxy groups at the position 4,5,6 of the bicyclic imide ring was performed to examine their potential anticancer effects against some cell lines. A multistep chemical pathway was used to synthesize the derivatives. The cytotoxic effect of trisubstituted isoindole derivatives were evaluated by determining cellular viability using the MTT assay against A549, PC‐3, HeLa, Caco‐2, and MCF‐7 cell lines. The C‐2 selective ring‐opening products were obtained from the ring‐opening reaction of 5‐alkyl/aryl‐2‐hydroxyhexahydro‐4H‐oxireno[2,3‐e]isoindole‐4,6(5H)‐diones with nucleophiles such as chloride (Cl−) and bromide (Br−) ions. In addition, the ring‐opening products halodiols were converted to their related acetates. The anticancer activity of synthesized isoindole‐1,3‐dione derivatives was investigated against HeLa, A549, MCF‐7, PC3, and Caco‐2 cells in vitro and resulted in varies cytotoxic effect depend on the group attached to the isoindole molecule. Furthermore, the evaluation of the antimicrobial action of trisubstituted isoindole derivatives against Gram‐positive (Staphylococcus aureus) and Gram‐negative (Escherichia coli) bacteria was assessed and found out selective inhibition of the both bacterial growth via different trisubstituted isoindole derivatives. The results of this work encourage further research on the potential utilization of trisubstituted isoindole derivatives as cytotoxic and antimicrobial agents.
- Subjects
CYTOTOXINS; RING-opening reactions; BACTERIAL growth; GRAM-negative bacteria; CELL lines; ISOBUTANOL; INDOLE derivatives; ISOINDOLE
- Publication
Chemical Biology & Drug Design, 2023, Vol 102, Issue 6, p1448
- ISSN
1747-0277
- Publication type
Article
- DOI
10.1111/cbdd.14335