NEW NEPLANOCIN ANALOGS .5. A POTENT ADENOSYLHOMOCYSTEINE HYDROLASE INHIBITOR LACKING ANTIVIRAL ACTIVITY - SYNTHESIS AND ANTIVIRAL ACTIVITY OF 6'-CARBOXYLIC ACID-DERIVATIVES OF NEPLANOCIN-A

The g-carboxylic acid derivative of neplanocin A 3 was synthesized fro m NPA, and was converted to the corresponding methyl ester 4 and amide s 5 and 6. These were evaluated for their anti-RNA-virus activities. O f the derivatives synthesized, only 5 was active against RNA viruses w ithin the concentration range of 0.14-4.88 mu g/mL. Compounds 3 and 5 showed a potent inhibitory effect on S-adenosylhomocysteine (AdoHcy) h ydrolase from rabbit erythrocytes. Although a close correlation betwee n the inhibitory effect of adenosine analogues on AdoHcy hydrolase and their antiviral potency has been demonstrated, 3 did not show any ant i-RNA-virus activities.