ACYCLIC ANALOGS OF NUCLEOSIDES - SYNTHESI S AND CYTOTOXIC PROPERTIES OF ACYL DERIVATIVES OF 3'(5')-AMINO-3'(5')-DEOXY-2',3'-SECOADENOSINE

Interaction of 3'-amino-3'-deoxy-2',3'-secoadenosine with the N-hydrox ysuccinimide esters of nicotinic or quinaldic acids and with 1-nitroan thraquinone-2-carboxylic acid in the presence of 2-ethoxy-1-ethoxy-car bonyl- 1,2-dihydroquinoline led to the corresponding amides. To obtain 5'-modified 2',3'-secoadenosine analogs, 5'-deoxy-5'-nicotinoylamido- , 5'-deoxy-5'-(quinoline-2-carbonylamido)- and 5'-deoxy-5'-[3-(3-indol yl)propionylamido]adenosine were subjected to the periodate oxidation - sodium borohydride reduction procedure. Structures of the synthesize d compounds were was confirmed by H-1 NMR spectroscopy. 2',3'-Diamino- 2',3'-dideoxy-, 3'-deoxy-3'-(quinoline-2-carbonylamido)- and 3-(3-(ind olyl)propionylamido]-2',3'-secoadenosines exhibited a cytotoxic effect on CaOv cells in vitro (CE(50) 10 - 30 mu M).