Synthesis and antimetastatic properties of steroeoisomeric trycylic bis(dioxopiperazine) analogues in a B16 melanoma model.
The synthesis for trans and cis tricyclic bis(dioxopiperazine)s 5 and 6 from pyrazine-2,3-dicarboxamide (7) is described. Stereoselective antimetastatic activity differences for these analogues were observed following pretreatment of B16-F10 melanoma cells in vitro. Activities for these isomers were compared with selected intermediates, and the data are discussed in relation to previous results obtained with cis- and trans-cyclopropane analogues.
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D008297:Male; D008545:Melanoma / Q000188:drug therapy*; D051379:Mice; D008810:Mice, Inbred C57BL; D009362:Neoplasm Metastasis / Q000517:prevention & control; D009374:Neoplasms, Experimental / Q000188:drug therapy; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D010879:Piperazines