Synthesis and biological activity of N6-(n-alkylureido)purine ribonucleosides and their 5'-phosphates.
Syntheses and biological activities of 12 N6-(n-alkylureido)purine ribonucleosides (alkyl chain length of 1--10, 16, and 18 carbons) and three N6-(n-alkylureido)purine ribonucleoside 5'-phosphates (chain length of 4, 9, and 10 carbons) are described. The N6-(n-alkylureido)purine ribonucleosides were prepared by a reaction of (2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl)-9H-purine-6-carbamate and n-alkylamine in refluxing pyridine. The 5'-nucleotides were prepared by direct phosphorylation of the corresponding ribonucleoside with phosphorus oxychloride and triethyl phosphate. Some N6-(n-alkylureido)purine ribonucleosides (n-octyl, n-nonyl, and n-decyl) and their nucleotides showed a marked antiproliferative activity against L-1210 cells in culture.
D000818:Animals; D002455:Cell Division / Q000187:drug effects; D002478:Cells, Cultured; D007939:Leukemia L1210 / Q000473:pathology; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D011685:Purine Nucleotides / Q000138:chemical synthesis* / Q000494:pharmacology; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D012265:Ribonucleotides / Q000138:chemical synthesis* / Q000494:pharmacology
D011684:Purine Nucleosides; D011685:Purine Nucleotides; D012263:Ribonucleosides; D012265:Ribonucleotides