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.
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Rohm and Haas Company, 727Norristown Road, Spring House, PA 19477-0904, USA. rsadhy@rohmhaas.com
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D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D003078:Colchicine / Q000737:chemistry; D003510:Cyclohexanes / Q000737:chemistry / Q000494:pharmacology*; D053138:Cyclohexenes; D006540:Herbicides / Q000737:chemistry / Q000494:pharmacology*; D009574:Nitro Compounds / Q000737:chemistry / Q000494:pharmacology*; D018517:Plant Roots / Q000166:cytology / Q000187:drug effects; D010947:Plants, Toxic; D013329:Structure-Activity Relationship; D014026:Nicotiana; D014404:Tubulin / Q000378:metabolism; D050257:Tubulin Modulators; D014407:Tumor Cells, Cultured
C433933:4-nitro-5-(2,3,4-trimethoxyphenyl)cyclohexene; D000970:Antineoplastic Agents; D003510:Cyclohexanes; D053138:Cyclohexenes; D006540:Herbicides; D009574:Nitro Compounds; D014404:Tubulin; D050257:Tubulin Modulators; C034672:1-phenylcyclohex-1-ene; D003078:Colchicine