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Synthesis of 3‐(β‐D‐ribofuranosyl)pyrazolo[3,2‐ i ]‐purine derivatives and their cytotoxic activities
Author(s) -
Hamamichi Norimitsu,
Miyasaka Tadashi
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300203
Subject(s) - chemistry , purine , nitration , stereochemistry , derivative (finance) , acetylation , pyrimidine , cytotoxic t cell , medicinal chemistry , organic chemistry , enzyme , biochemistry , financial economics , economics , in vitro , gene
9‐Amino‐3‐(β‐D‐ribofuranosyl)pyrazolo[3,2‐ i |purine ( 6 ) has been prepared from a fully protected 3‐(β‐D‐ribofuranosyl)pyrazolo[3,2‐ i ]purine ( 2 ) and the 9‐bromo substituted derivative 3 by nitration, followed by reduction. Reaction of 9‐bromo‐3‐(β‐D‐ribofuranosyl)pyrazolo[3,2‐ i )purine ( 1b ) with alkali gave the (pyrazol‐3‐yl)imidazole derivative, followed by diazocyclization with sodium nitrate to give 9‐bromo‐3‐(β‐D‐ribofuran‐osyl)imidazolo[4,5‐ d ]pyrazolo[2,3‐ c ][1,2,3]triazine ( 10 ) after deacetylation. Compounds 6 and 10 exhibited cytotoxic activity against leukemia cells.