Synthesis and antitumor activity of spergualin analogues. I. Chemical modification of 7-guanidino-3-hydroxyacyl moiety.
Many analogues and derivatives of an antitumor antibiotic, spergualin, were synthesized, and the relationships between the structure and the activity against mouse L-1210 tumor were studied. Both modification of the 15-hydroxyl group and alteration of chain-length of the omega-guanidinoacyl moiety affected the activity. 15-Deoxyspergualin (18, 1-amino-19-guanidino-11-hydroxy-4,9,12-triazanonadecane-10,13-d ion e) and its analogue 25 (1-amino-21-guanidino-11-hydroxy-4,9,12-triazauneicosane-10,13-dio ne) had strong activity, superior to that of spergualin.
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000627:therapeutic use; D002264:Carboxylic Acids; D002384:Catalysis; D004353:Drug Evaluation, Preclinical; D006146:Guanidines / Q000138:chemical synthesis / Q000627:therapeutic use; D007939:Leukemia L1210 / Q000188:drug therapy; D008297:Male; D051379:Mice; D013095:Spermidine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D002264:Carboxylic Acids; D006146:Guanidines; C033797:spergualin; C046605:glyoxylylspermidine; D013095:Spermidine