Synthesis and pharmacological evaluation of some new fluorine containing hydroxypyrazolines as potential anticancer and antioxidant agents

Eur J Med Chem. 2015 Nov 2:104:25-32. doi: 10.1016/j.ejmech.2015.09.029. Epub 2015 Sep 28.

Abstract

Breast cancer is probably the most prevalent cancer in women. The development of resistance to therapeutic agents and lack of targeted therapy for breast cancer cells provide motivation to identify new compounds for the treatment. With this objective in mind, a new series of 3-fluoro-4-methoxyphenyl group based 1,3,5-trisubstituted aryl-5-hydroxypyrazoline analogues 4a-l was synthesized through multi-step reaction sequence. The structures of the newly synthesized compounds were confirmed by IR, (1)H NMR, (13)C NMR, LC-MS and elemental analysis. They were screened for their in vitro anticancer and in vitro antioxidant activities. Among the tested compounds 4h, 4c and particularly 4i displayed promising cytotoxic effect on breast cancer cell lines. The compounds were also found to possess antioxidant activity when tested against DPPH free radical. Overall, this work has contributed to the development of promising leads for anticancer and antioxidant activities.

Keywords: Anticancer activity; Antioxidant activity; Characterization; Hydroxypyrazolines; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Biphenyl Compounds / antagonists & inhibitors
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Chlorocebus aethiops
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fluorine / chemistry
  • Fluorine / pharmacology*
  • Free Radicals / antagonists & inhibitors
  • Humans
  • MCF-7 Cells
  • Models, Molecular
  • Molecular Structure
  • Picrates / antagonists & inhibitors
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Structure-Activity Relationship
  • Vero Cells

Substances

  • 5-hydroxypyrazoline
  • Antineoplastic Agents
  • Antioxidants
  • Biphenyl Compounds
  • Free Radicals
  • Picrates
  • Pyrazoles
  • Fluorine
  • 1,1-diphenyl-2-picrylhydrazyl