Phosphorus--nitrogen compounds XXIII: Oncolytic phosphorylated imines.
A series of 15 amidine, iminopiperidine, iso(thio)urea, and guanidine derivatives and six 2,5-dihydro-1,3,5,2-triazaphosphorines were synthesized. Most of the compounds were tested for ability to react with L-cysteine and for antitumor activity against sarcoma 180 and P-388 murine tumor systems. Three acyclic phosphorylated imines and one triazaphosphorine showed activity in the former model to indicate that the P(O)N = C grouping serves as an oncolytic moiety. All agents condensed with L-cysteine with the active antitumor compounds displaying a tendency for relatively higher reactivity with this amino acid.
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D003545:Cysteine; D007097:Imines / Q000138:chemical synthesis* / Q000494:pharmacology; D007941:Leukemia P388 / Q000188:drug therapy; D008297:Male; D051379:Mice; D012510:Sarcoma 180 / Q000188:drug therapy
D000970:Antineoplastic Agents; D007097:Imines; D003545:Cysteine