Structure-activity relationships of phenylcyclohexene and biphenyl antitubulin compounds against plant and mammalian cells

Bioorg Med Chem Lett. 2001 Jun 4;11(11):1393-6. doi: 10.1016/s0960-894x(01)00246-3.

Abstract

Phenylcyclohexenes (PCHs) [e.g., trans-4-nitro-5-(2,3,4-trimethoxyphenyl)cyclohexene, 2d] were found to bind weakly to the colchicine site of bovine tubulin, but are the first mimics of colchicine found to have high activity towards plant cells. Structure-activity relationships for PCHs and biphenyl AC-ring analogues of colchicine (e.g., 2,3,4,4'-tetramethoxy-2'-methyl-1,1'-biphenyl, 3e) are discussed.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Division / drug effects
  • Colchicine / chemistry
  • Cyclohexanes / chemistry
  • Cyclohexanes / pharmacology*
  • Cyclohexenes
  • Herbicides / chemistry
  • Herbicides / pharmacology*
  • Nitro Compounds / chemistry
  • Nitro Compounds / pharmacology*
  • Plant Roots / cytology
  • Plant Roots / drug effects
  • Plants, Toxic
  • Structure-Activity Relationship
  • Tobacco
  • Tubulin / metabolism
  • Tubulin Modulators*
  • Tumor Cells, Cultured

Substances

  • 4-nitro-5-(2,3,4-trimethoxyphenyl)cyclohexene
  • Antineoplastic Agents
  • Cyclohexanes
  • Cyclohexenes
  • Herbicides
  • Nitro Compounds
  • Tubulin
  • Tubulin Modulators
  • 1-phenylcyclohex-1-ene
  • Colchicine