The Synthesis of 2-Substituted 1, N⁶-Etheno-adenosine-3', 5'-cyclic Phosphate by Ring Reclosure of Alkali-hydrolizate of 1, N⁶-Etheno-adenosine-3', 5'-cyclic Phosphate

抄録

An useful procedure for the synthesis of 2-substituted 1, N⁶-etheno-adenosine-3', 5'-cyclic phosphates by ring closure of 3-β-D-(3', 5'-cyclic phospho)-ribofuranosyl-4-amino-5-(imidazol-2-yl)-imidazole (II), under relative mild conditions, is reported. Treatment of the compound II with bromine cyanide, triethyl orthoacetate, 1, 1'-carbonyldiimidazole and carbon disulfide gave 2-amino-, 2-methyl-, 2-hydroxy-, and 2-mercapto-1, N⁶-etheno-adenosine-3', 5'-cyclic phosphate (c-AMP), respectively. Moreover, several 2-alkylmercapto-, 2-benzylmercapto-, and 2-bromo-1, N⁶-etheno-c-AMP were synthesized from 2-merc apto-1, N⁶-etheno-c-AMP. 2-Methoxy-, 2-azido-, 2-dimethylamino-1, N⁶-etheno-c-AMP were synthesized from 2-bromo-1, N⁶-etheno-c-AMP. The fluorescent and ultraviolet spectra of 2-substituted 1, N⁶-etheno-c-AMP are tabulated.