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Synthesis, anticancer, structural, and computational docking studies of 3-benzylchroman-4-one derivatives

Lalitha Simon1, Abdul Ajees Abdul Salam2, S Madan Kumar3

  • 1Department of Chemistry, Manipal Institute of Technology, Manipal University, Manipal 576 104, India.

Bioorganic & Medicinal Chemistry Letters
|October 28, 2017
PubMed

Insights

New anticancer drug candidates, 3-Benzylchroman-4-ones, show promise. Compound 3b is effective against breast cancer cells, while 3h targets cervical cancer cells, indicating potential for novel cancer therapies.

Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Pharmacology

Background:

  • Cancer remains a leading cause of mortality worldwide, necessitating the development of novel therapeutic agents.
  • Chroman-4-one derivatives have demonstrated a range of biological activities, including anticancer properties.

Purpose of the Study:

  • To synthesize a series of 3-Benzylchroman-4-one compounds.
  • To evaluate the in vitro anticancer activity of these synthesized compounds against human breast carcinoma (BT549) and cervical carcinoma (HeLa) cell lines.
  • To investigate the structure-activity relationships and potential mechanisms of action.

Main Methods:

  • Synthesis of 3-Benzylchroman-4-one derivatives using established organic chemistry protocols.
  • Anticancer activity screening using the MTT assay against BT549, HeLa, and Vero (normal kidney epithelial) cell lines.
  • Determination of IC50 values to quantify compound potency.
  • Single crystal X-ray crystallography for structural elucidation of key compounds (3h, 3i).
  • Molecular docking studies of lead compounds with the tumor suppressor protein p53.

Main Results:

  • Several 3-Benzylchroman-4-one derivatives were successfully synthesized.
  • Compound 3b exhibited significant activity against BT549 cells with an IC50 of 20.1 µM.
  • Compound 3h demonstrated potent activity against HeLa cells with an IC50 of 20.45 µM and moderate activity against BT549 cells (IC50 = 42.8 µM).
  • The molecular structures of 3h and 3i were confirmed by X-ray crystallography.
  • Molecular docking suggested potential interactions between compound 3h and the p53 protein.

Conclusions:

  • The synthesized 3-Benzylchroman-4-one derivatives represent a promising class of anticancer agents.
  • Compounds 3b and 3h display selective and potent activity against specific cancer cell lines, warranting further investigation.
  • Structural and computational studies provide insights into the potential mechanism of action, particularly the interaction with p53.
Keywords:
Benzylchroman-4-onesCytotoxicityMTT assayMolecular dockingSingle crystal

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