Synthesis and antiproliferative activity of a new compound containing an alpha-methylene-gamma-lactone group

J Med Chem. 2002 Jun 6;45(12):2358-61. doi: 10.1021/jm025518n.

Abstract

The biological activity of compound 9 obtained by introducing an alpha-methylene-gamma-butyrolactone group into 3-(4-hydroxyphenyl)propionic acid, 1, was studied for possible effects on HL-60 cells, murine splenocytes, and human peripheral mononuclear cells (PBMC). 9 induced apoptosis in the HL-60 cell line and has a clear capacity to inhibit proliferation induced in murine splenocytes and PBMC by different mitogenic agents with no apparent toxic side effects. 9 was synthesized from 1, and its structure and stereochemistry were elucidated by spectroscopic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • 4-Butyrolactone / chemical synthesis*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / pharmacology
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Apoptosis
  • Cells, Cultured
  • Drug Screening Assays, Antitumor
  • Humans
  • Mice
  • Structure-Activity Relationship

Substances

  • 5-(2-(4-methoxyphenyl)ethyl)-3-methylene-4-methyldihydrofuran-2-one
  • Antineoplastic Agents
  • 4-Butyrolactone