Synthesis, evaluation and quantitative structure-activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents

Bioorg Med Chem Lett. 2017 Feb 15;27(4):1012-1016. doi: 10.1016/j.bmcl.2016.12.076. Epub 2017 Jan 5.

Abstract

A novel series of 49 wogonin derivatives were synthesized by introducing group at 7-, 8- or B ring of wogonin. The cytotoxic activities against HepG2, A549 and BCG-823 cancer cell lines were also investigated in vitro. Several of them showed obvious cytotoxic activities and compound 3h possessed the highest potency against HepG2, A549, and BCG-823 with IC50 values of 1.07μM, 1.74μM and 0.98μM, respectively. A quantitative structure-activity relationship (QSAR) study of these synthetic derivatives as well as wogonin indicated that high solubility and low octanol/water partition coefficient are favorable, and excessive electrostatic properties and refractivity are unfavorable for the cytotoxic activities of these wogonin derivatives. These findings and results provide a base for further investigations.

Keywords: Cytotoxic; Flavonoid; QSAR; Wogonin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Flavanones / chemistry
  • Flavanones / pharmacology*
  • Humans
  • Quantitative Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Flavanones
  • wogonin