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

Lalitha Simon; Abdul Ajees Abdul Salam; S Madan Kumar; T Shilpa; K K Srinivasan; K Byrappa

doi:10.1016/j.bmcl.2017.10.026

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

Bioorg Med Chem Lett. 2017 Dec 1;27(23):5284-5290. doi: 10.1016/j.bmcl.2017.10.026. Epub 2017 Oct 16.

Authors

Lalitha Simon¹, Abdul Ajees Abdul Salam², S Madan Kumar³, T Shilpa⁴, K K Srinivasan⁵, K Byrappa⁶

Affiliations

¹ Department of Chemistry, Manipal Institute of Technology, Manipal University, Manipal 576 104, India.
² Department of Atomic and Molecular Physics, Manipal Institute of Technology, Manipal University, Manipal 576 104, India. Electronic address: abdul.ajees@manipal.edu.
³ PURSE Lab, Mangalagangotri, Mangalore University, Mangalore 574 199, India.
⁴ Department of Atomic and Molecular Physics, Manipal Institute of Technology, Manipal University, Manipal 576 104, India.
⁵ Department of Chemistry, Shri Madhwa Vadiraja Institute of Technology and Management, Vishwothama Nagar, Bantakal, Udupi 576 115, India.
⁶ Department of Material Science, Mangalagangotri, Mangalore University, Mangalore 574 199, India.

PMID: 29074256
DOI: 10.1016/j.bmcl.2017.10.026

Abstract

A series of 3-Benzylchroman-4-ones were synthesized and screened for anticancer activity by MTT assay. The compounds were evaluated against two cancerous cell lines BT549 (human breast carcinoma), HeLa (human cervical carcinoma), and one noncancerous cell line vero (normal kidney epithelial cells). 3b was found to be the most active molecule against BT549 cells (IC₅₀ = 20.1 µM) and 3h against HeLa cells (IC₅₀ = 20.45 µM). 3b also exhibited moderate activity against HeLa cells (IC₅₀ = 42.8 µM). The molecular structures of 3h and 3i were solved by single crystal X-ray crystallographic technique. Additionally, the molecular docking studies between the tumour suppressor protein p53 with the lead compound 3h, which exhibited better anticancer activity against HeLa cells was examined.

Keywords: Benzylchroman-4-ones; Cytotoxicity; MTT assay; Molecular docking; Single crystal.

MeSH terms

Animals
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Chlorocebus aethiops
Crystallography, X-Ray
Dose-Response Relationship, Drug
Humans
Molecular Docking Simulation*
Molecular Structure
Structure-Activity Relationship
Vero Cells

Substances

Antineoplastic Agents