Novel Indole-Tethered Chromene Derivatives: Synthesis, Cytotoxic Properties, and Key Computational Insights

M. Shaheer Malik, Hissana Ather, Shaik Mohammad Asif Ansari, Ayesha Siddiqua, Qazi Mohammad Sajid Jamal, Ali H. Alharbi, Munirah M. Al-Rooqi, Rabab S. Jassas, Essam M. Hussein, Ziad Moussa, Rami J. Obaid, Saleh A. Ahmed

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Indole-tethered chromene derivatives were synthesised in a one-pot multicomponent reaction using N-alkyl-1H-indole-3-carbaldehydes, 5,5-dimethylcyclohexane-1,3-dione, and malononitrile, catalysed by DBU at 60–65 °C in a short reaction time. The benefits of the methodology include non-toxicity, an uncomplicated set-up procedure, a faster reaction time, and high yields. Moreover, the anticancer properties of the synthesised compounds were tested against selected cancer cell lines. The derivatives 4c and 4d displayed very good cytotoxic activity, with IC50 values ranging from 7.9 to 9.1 µM. Molecular docking revealed the potent derivatives have good binding affinity towards tubulin protein, better than the control, and the molecular dynamic simulations further demonstrated the stability of ligand-receptor interactions. Moreover, the derivatives followed all the drug-likeness filters.

Original languageEnglish
Article number333
JournalPharmaceuticals
Volume16
Issue number3
DOIs
Publication statusPublished - Mar 2023

Keywords

  • ADME
  • anti-cancer activity
  • chromenes
  • indole
  • molecular docking
  • multicomponent reaction

ASJC Scopus subject areas

  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery

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