Synthesis, biological evaluation and SAR analysis of O-alkylated analogs of quercetin for anticancer

Bioorg Med Chem Lett. 2014 Sep 15;24(18):4424-4427. doi: 10.1016/j.bmcl.2014.08.006. Epub 2014 Aug 10.

Abstract

O-Alkylated quercetin analogs were synthesized and their anticancer activities were assessed by a high-throughout screening (HTS) method. The structure-activity relationships (SAR) showed that introduction of long alkyl chain such as propyl group at the C-3 OH position or short alkyl chain such as ethyl group at the C-4' OH position were very important for keeping inhibitory activities against the 16 cancer cell lines. Furthermore, when the two n-butyl groups were introduced into the C-3, C-7 or C-4', C-7 positions, the anticancer activity was enhanced.

Keywords: Alkylation; Anticancer; Quercetin; Structure–activity relationship.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • High-Throughput Screening Assays
  • Humans
  • Molecular Structure
  • Quercetin / chemical synthesis
  • Quercetin / chemistry
  • Quercetin / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Quercetin