GB1428539A - Substituted adenosine cyclophosphates - Google Patents

Abstract

1428539 Purine nucleotides MAX-PLANCKGES ZUR FORDERUNG DER WISSENSCHAFTEN eV 24 July 1973 [25 July 1972] 35110/73 Headings C2P and C2C The invention comprises compounds of formula where X is hydrogen and R is 2,4-dinitrophenyl or where X is Cl or Br and R is H and the salts thereof with physiologically compatible acids and bases. Compounds of Formula I in which X is chlorine or bromine may be prepared by phosphorylating 2-chloro- or 2-bromoadenosine with phosphorus oxychloride and cyclizing the reaction product, which may be isolated with dicyclohexylcarbodiimide in a strongly polar organic solvent. Compounds of Formula I in which R is dinitrophenyl may be prepared by reacting adenosine-3,5<SP>1</SP>-cyclophosphate with 2,4-dinitrofluorobenzene in the presence of diisopropylethylamine in a polar organic solvent. The starting materials 2-chloro- and 2-bromoadenosine may be prepared by reacting 2,6- dichloro- or 2,6-dibromopurine with beta-D- ribofuranose 1,2,3,5-tetraacetate in the presence of toluene sulphonic acid to give 9-(tri-O-acetylbeta - D - ribofuranosyl) - 2,6 - dichloro- or -2,6-dibromopurine and reacting this product, dissolved in anhydrous methanol, with ammonia. Compounds of Formula I in which R is 2,4- dinitrophenyl may be reduced to give a corresponding compound in which R is 2,4-diaminophenyl. Compounds of Formula I in which X is halogen may be used to prepare adenosine-3<SP>1</SP>,5<SP>1</SP>- cyclophosphate derivatives substituted in the 2-position by methoxy, methylthio, dimethylamino, methylamino, hydrazino or azido. The compounds of Formula I have pharmaceutical properties and may be used as the active ingredients in conventional pharmaceutical compositions.