Podophyllotoxin analogs. 1. Synthesis and biological evaluation of certain trans-2-aryl-trans-6-hydroxymethyl-3-cyclohexenecarboxylic acid gamma-lactones as antimitotic agents.
A series of cis and trans bicyclic lactones was prepared as congeners of podophyllotoxin (1) and evaluated as antimitotic agents both in cell cultures grown in vitro and in an in vitro protein binding assay. All compounds displayed insignificant activity-a result which may reflect insufficient structural similarity to podophyllotoxin or which may be interpreted as in agreement with previous observations of the stereochemical requirements for antimitotic activity defined for 1.
D000818:Animals; D001853:Bone Marrow / Q000378:metabolism; D001854:Bone Marrow Cells; D001921:Brain / Q000378:metabolism; D002417:Cattle; D002999:Clone Cells / Q000378:metabolism; D003078:Colchicine / Q000378:metabolism; D003509:Cyclohexanecarboxylic Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D003864:Depression, Chemical; D006410:Hematopoiesis / Q000187:drug effects; D066298:In Vitro Techniques; D007783:Lactones / Q000138:chemical synthesis / Q000494:pharmacology; D012515:Mast-Cell Sarcoma / Q000378:metabolism; D008938:Mitosis / Q000187:drug effects*; D011034:Podophyllotoxin / Q000031:analogs & derivatives* / Q000494:pharmacology; D011485:Protein Binding / Q000187:drug effects; D012513:Sarcoma, Experimental / Q000378:metabolism; D014404:Tubulin / Q000378:metabolism
D003509:Cyclohexanecarboxylic Acids; D007783:Lactones; D014404:Tubulin; D011034:Podophyllotoxin; D003078:Colchicine