8-Phosphorus substituted isosteres of purine and deazapurines.

Abstract:

:Synthesis of 8-phosphorus substituted isosteres of purine [pyrimidino (4,5-d)-1,3,2-diazaphosphole], 1-deazapurine [pyridino (2,3-d)-1,3,2-diazaphosphole] and 3-deazapurine [pyridino (4,5-d)-1,3,2-diazaphosphole] has been achieved by the reaction of equimolar amounts of triphenylphosphite and 4,5-diaminopyrimidine, 2,3-diaminopyridine and 3,4-diaminopyridine, respectively. These compounds hydrolyzed (cleavage of the phosphorus-nitrogen bounds) in aqueous solutions to provide the corresponding diaminopyrimidine or diaminopyridines. These three new basic ring systems constitute the first reported synthesis of purines in which ring carbon atom is substituted with a phosphorus atom. 8-Phosphorus substituted purine at a concentration of 4 X 10(-4)M caused a 50% inhibition in the growth of leukemia L1210 cells in culture. The biochemical rationale for the synthesis of these compounds is discussed.

journal_name

Nucleic Acids Res

journal_title

Nucleic acids research

authors

Khwaja TA,Pande H

doi

10.1093/nar/7.1.251

subject

Has Abstract

pub_date

1979-09-11 00:00:00

pages

251-8

issue

1

eissn

0305-1048

issn

1362-4962

journal_volume

7

pub_type

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