Synthesis and cytotoxicity of 2-acetyl-4,8-dihydrobenzodithiophene-4, 8-dione derivatives

J Med Chem. 1998 Nov 5;41(23):4658-61. doi: 10.1021/jm980394t.

Abstract

2-Acetyl-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (9) and 2-acetyl-4,8-dihydrobenzo[1,2-b:5,4-b']dithiophene-4,8-dione (19), together with 10 related mono- and disubstituted derivatives, were synthesized and evaluated in vitro by NCI against eight cancer types. All compounds showed significant activity against melanoma, HL-60 leukemia, NCI-H23 non-small-cell lung cancer, OVCAR-3 ovarian cancer, and MDA-MB-435 and MDA-N breast cancer cell lines. Compound 11, 2-(1'-acetoxyethyl)-4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4, 8-dione, showed the highest overall potency (mean GI50 = 40 nM).

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Inhibitory Concentration 50
  • Structure-Activity Relationship
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry
  • Thiophenes / pharmacology
  • Tumor Cells, Cultured

Substances

  • 2-(1'-acetoxyethyl)-4,8-dihydrobenzo(1,2--4,5-b')dithiophene-4,8-dione
  • Antineoplastic Agents
  • Thiophenes