SYNTHESIS OF MODIFIED PURINE RIBONUCLEOSI DES 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 gav e 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-methoxytryptamin e using the active esters method. The reaction of 2',3'-O-isopropylide neadenosine with 3-[(5-methoxy-3-indolyl)ethylamido]propionic acid in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine r esulted in the (5-methoxy-3-indolyl)ethylamino]succinyladenosine. This compound was also synthesized from ',3'-O-isopropylidene-5'O-hydroxys uccinyladenosine and 5-methoxytryptamine using the method of active es ters. Starting from 5'-amino-5'-deoxy-2',3'-O-isopropilydeneadenosine and N-hydroxysuccinimide esters of nicotinic, quinaldic, and 3-indolyl propionic acids, 5'-deoxy-5'-nicotinoyl-, 5'-deoxy-5'-(quinoline-2-car bonyl)-, and 5'-deoxy-5'(3-indolylpropionyl)aminoadenosine, respective ly, were synthesized, The compounds prepared were found not to influen ce the thymidine incorporation into DNA of CaOv cells in vitro.