Synthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenes and their analogues

Arch Pharm (Weinheim). 2007 May;340(5):244-50. doi: 10.1002/ardp.200600146.

Abstract

A total synthetic route for two natural dihydrostilbenes with significant cytotoxicity toward human cancer cell lines, (3-(2-(7-methoxybenzo[d][1,3]dioxol-5-yl)ethyl)phenol 1a and 6-(3-hydroxyphenethyl)benzo[d][1,3]dioxol-4-ol 1b), which were isolated from Bulbophyllum odoratissimum Lindl, was developed via Wittig-Horner reaction. The natural products 1a and 1b were obtained in 28% and 20% overall yield, respectively. Additionally, nine analogues, 1c-1k, of the two natural dihydrostilbenes were synthesized and evaluated for their anti-proliferative activity against human SGC-7901, KB and HT-1080 cell lines by MTT assay. The activities of 1c and 1d were in the same range as those of the natural products 1a and 1b.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Benzoxazines / chemical synthesis
  • Benzoxazines / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects*
  • Colorimetry
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Orchidaceae / chemistry*
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry
  • Stilbenes / pharmacology
  • Structure-Activity Relationship

Substances

  • 6-bromo-3-(4-butylphenyl)-1,3-benzoxazine-2,4-(3H)-dione
  • Antineoplastic Agents, Phytogenic
  • Benzoxazines
  • Stilbenes