Yasuyoshi Saito

New neplanocin analogues. III: 6'R-configuration is essential for the antiviral activity of 6'-C-methyl-3-deazaneplanocin A's

(6′ R )- and (6′ S -6′- C -methyl-3-deazaneplanocin As were synthesized from D-ribose as anti-RNA virus agents. Of these compounds, (6′ R )-6′- C -methyl-3-deazaneplanocin A ( 4b ) showed the greatest anti-RNA virus activity in vitro . It was found that the 6′ R -configuration was essential for the antiviral activity of 6′- C -methylneplanocin A derivatives.

New Neplanocin Analogues. V. A Potent Adenosylhomocysteine Hydrolase Inhibitor Lacking Antiviral Activity. Synthesis And Antiviral Activity Of 6″-Carboxylic Acid Derivatives Of Neplanocin A 1

Abstract The 6′-carboxylic acid derivative of neplanocin A 3 was synthesized from NPA, and was converted to the corresponding methyl ester 4 and amides 5 and 6. These were evaluated for their anti-RNA-virus activities. Of the derivatives synthesized, only 5 was active against RNA viruses within the concentration range of 0.14-4.88 μg/mL. Compounds 3 and 5 showed a potent inhibitory effect on S-adenosylhomocysteine (AdoHcy) hydrolase from rabbit erythrocytes. Although a close correlation between the inhibitory effect of adenosine analogues on AdoHcy hydrolase and their antiviral potency has been demonstrated, 3 did not show any anti-RNA-virus activities. 1This paper constitutes part 146 of Nucleosides and Nucleotides. Part 145. Shuto, S.; Haramuishi, K.; Matsuda, A. Tetrahedron Lett. Submitted.