Synthesis and structure-activity relationships of 3-aminobenzophenones as antimitotic agents

J Med Chem. 2004 May 20;47(11):2897-905. doi: 10.1021/jm0305974.

Abstract

A new series of 3-aminobenzophenone compounds as potent inhibitors of tubulin polymerization was discovered based on the mimic of the aminocombretastatin molecular skeleton. Lead compounds 5 and 11, with alkoxy groups at the C-4 position of B-ring, were potent cytotoxic agents and inhibitors of tubulin polymerization through the binding to the colchicine-binding site of tubulin. The corresponding antitubulin activities of 5 and 11 were similar to or greater than combretastatin A-4 and AVE-8063. Replacement of the methoxy group with a chloro group in the B ring of aminobenzopheneones (3, 8, and 9) caused drastic decrease in cytotoxic and antitubulin activity except in compounds 4 and 10, which could result from a unique alignment between chloro and amino groups located at the para position to each other. SAR information revealed that introduction of an amino group at the C-3 position in B ring of benzophenones, in addition to a methoxy group at the C-4 position, plays an important role for maximal cytotoxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemical synthesis*
  • Aniline Compounds / chemistry*
  • Aniline Compounds / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Benzophenones / chemical synthesis*
  • Benzophenones / chemistry
  • Benzophenones / pharmacology
  • Biopolymers
  • Cell Division / drug effects
  • Cell Line, Tumor
  • Colchicine / chemistry
  • Drug Resistance, Multiple
  • Drug Resistance, Neoplasm
  • Drug Screening Assays, Antitumor
  • Humans
  • Protein Binding
  • Stilbenes / chemical synthesis*
  • Stilbenes / chemistry*
  • Stilbenes / pharmacology
  • Structure-Activity Relationship
  • Tubulin / chemistry

Substances

  • AVE-8063
  • Aniline Compounds
  • Antineoplastic Agents
  • Benzophenones
  • Biopolymers
  • Stilbenes
  • Tubulin
  • Colchicine