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

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.