Biological activity and a modified synthesis of 8-amino-3-beta-D-ribofuranosyl-1,2,4-triazolo[4,3-a]pyrazine, an isomer of formycin.
A two-step synthesis of 8-amino-3-beta-D-ribofuranosyl-1,2,4-triazolo[4,3-a]pyrazine (3), which is an isomer of formycin that resembles 3-deazaadenosine, is reported. Compound 3 is also described as as being a very poor substrate for adenosine deaminase and to be both a competitive and an irreversible inhibitor of S-adenosylhomocysteinase in the synthesis direction. L1210 cell growth in culture was inhibited by 3. Compound 3 was not converted to the nucleotide level in erythrocytes but was found to inhibit both the cellular uptake of nucleic acid precursors and their incorporation into the nucleic acids of L1210 cells. Finally, 3 was found to be a weak antiviral agent and coronary vasodilator.
D000243:Adenosine Deaminase / Q000378:metabolism; D043383:Adenosylhomocysteinase; D000818:Animals; D000903:Antibiotics, Antineoplastic; D002455:Cell Division / Q000187:drug effects; D004285:Dogs; D005573:Formycins; D006867:Hydrolases / Q000037:antagonists & inhibitors; D007536:Isomerism; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D011719:Pyrazines / Q000138:chemical synthesis* / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D014664:Vasodilation / Q000187:drug effects
D000903:Antibiotics, Antineoplastic; D005573:Formycins; D011719:Pyrazines; D014230:Triazoles; C041855:8-amino-3-D-ribofuranosyl-1,2,4-triazolo(4,3-a)pyrazine; D006867:Hydrolases; D043383:Adenosylhomocysteinase; D000243:Adenosine Deaminase