Synthesis of Benzophenones and in vitro Evaluation of Their Anticancer Potential in Breast and Prostate Cancer Cells

ChemMedChem. 2019 May 17;14(10):1041-1048. doi: 10.1002/cmdc.201900127. Epub 2019 Apr 24.

Abstract

Breast and prostate cancers are frequently treated with chemotherapy. Several novel chemicals are being reported for this purpose, particularly synthetic and natural benzophenones. This work reports the synthesis of substituted 2-hydroxybenzophenones through 1,4-conjugate addition/intramolecular cycloaddition/dehydration of nitromethane on key intermediate chromones. Structures were extensively studied by means of 2D NMR spectroscopy and single-crystal XRD. Their cytotoxicity was evaluated in vitro in two breast cancer cell lines (MDA-MB-231 and T47-D) and one prostate cancer cell line (PC3). The most potent compound exhibited good cytotoxic effects against the three cancer cell lines (IC50 values ranging from 12.09 to 26.49 μm) and induced cell-cycle retardation only on prostate cancer cells, which suggested that it might exert cell-type-specific effects.

Keywords: benzophenones; cancer; cytotoxicity; drug design; synthesis design.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Apoptosis
  • Benzophenones / chemical synthesis*
  • Benzophenones / pharmacology
  • Breast Neoplasms / drug therapy*
  • Cell Line, Tumor
  • Cell Survival
  • Cycloaddition Reaction
  • Drug Screening Assays, Antitumor / methods
  • Female
  • Humans
  • Male
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Models, Molecular
  • Molecular Structure
  • Nitroparaffins / chemistry
  • Prostatic Neoplasms / drug therapy*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Benzophenones
  • Nitroparaffins
  • Methane
  • nitromethane