SYNTHESIS OF MODIFIED PURINE RIBONUCLEOSIDES FROM 3'(5')-O-SUCCINYLADENOSINE AND 5'-AMINO-5'-DEOXYADENOSINE

A reaction between 3'-O-hydroxysuccinyladenosine and 1-aminoadamantane in the presence of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline gave 3'-O-(1-adamantylamino)succinyladenosine. 2',5'-Di-O-acetyl-3'-O-[(5- methoxy-3-indolyl)ethylamino]succinyladenosine was synthesized from 2',5'-di-O-acetyl-3'-O-hydroxysuccinyladenosine and 5-methoxytryptamine using the active esters method. The reaction of 2',3'-O-isopropylideneadenosine with 3-[(5-methoxy-3-indolyl)ethylamido]propionic acid in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine resulted in the 2',3'-O-isopropylidene-5'-O-[(5-methoxy-3-indolyl)ethylamino]succinyladenosine. This compound was also synthesized from 2',3'-O-isopropylidene-5'O-hydroxysuccinyladenosine and 5-methoxytryptamine using the method of active esters. Starting from 5'-amino-5'-deoxy-2',3'-O-isopropilydeneadenosine and N-hydroxysuccinimide esters of nicotinic, quinaldic, and 3-indolylpropionic acids, 5'-deoxy-5'-nicotinoyl-, 5'-deoxy-5'-(quinoline-2-carbonyl)-, and 5'-deoxy-5'(3-indolylpropionyl)aminoadenosine, respectively, were synthesized, The compounds prepared were found not to influence the thymidine incorporation into DNA of CaOv cells in vitro.