55470-35-4Relevant academic research and scientific papers
Pyrrolopyrimidine nucleosides. VIII. Synthesis of sangivamycin derivatives possessing exocyclic heterocycles at C5
Schram,Townsend
, p. 39 - 54 (2007/10/08)
The effect on antileukemic activity exerted by introduction of exocyclic heterocyclic rings at the 5 position of 4 amino 7 (βD ribofuranosyl)pyrrolo[2,3 d]pyrimidine has been studied. Ring closures on the cyano group of toyocamycin were effected using various 1,3 dipolar addition reactions to form 5 and 6 membered heterocyclic rings. Condensation of 4 amino 7 (βD ribofuranosyl)pyrrolo[2,3 d]pyrimidine 5 carboxamidrazone with diketones led to substituted as triazines while aldehydes furnished certain 1,2,4 trizoles. Preparation of a 1,2,4 oxadiazole was achieved using 4 amino 7 (βD ribofuranosyl)pyrrolo[2,3 α]pyrimidine 5 carboxamidoxime. Ring annulation of 4 amino 7 (βD ribofuranosyl)pyrrolo[2,3 d]pyrimidine 5 thiocarboxamide with phenacyl bromide furnished a thiazole derivative. Testing data indicated that a 6 membered nonaromatic ring is the largest group which can be accommodated at C5 without complete loss of activity. All the 5 membered heterocyclic rings showed some activity. Activity was highest when the ring was nonaromatic and a 5 membered nonaromatic ring was more active than a 6 membered nonaromatic ring. None of these derivatives were as active as the compounds with smaller nonannulated groups at position 5.
