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• W2419105743 abstract "On the basis of the potent inhibitory activity of neplanocin A (1) against S-adenosylhomocysteine (AdoHcy) hydrolase, we analyzed the comprehensive structure-activity relationships by modifying the adenine and carbasugar moiety of 1 to find the pharmacophore in the active site of the enzyme. The introduction of 7-deazaadenine instead of adenine eliminated the inhibitory activity against the AdoHcy hydrolase, while 3-deazaadenine maintained the inhibitory activity of the enzyme, indicating that N-7 is essential for its role as a hydrogen bonding acceptor. The substitution of hydrogen at the 6'-position with fluorine increased the inhibitory activity of the enzyme. The one-carbon homologation at the 5'-position generally decreased the inhibitory activity of the enzyme, indicating that steric repulsion exists. A molecular docking study also supported these experimental data. In this study, 6'-fluoroneplanocin A (2) was the most potent inhibitor of AdoHcy hydrolase (IC50 = 0.24 μM). It showed a potent anti-VSV activity (EC50 = 0.43 μM) and potent anticancer activity in all the human tumor cell lines tested." @default.
• W2419105743 created "2016-06-24" @default.
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• W2419105743 date "2015-06-05" @default.
• W2419105743 modified "2023-10-17" @default.
• W2419105743 title "Structure–Activity Relationships of Neplanocin A Analogues as <i>S</i>-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities" @default.
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• W2419105743 doi "https://doi.org/10.1021/acs.jmedchem.5b00553" @default.
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• W2419105743 hasPublicationYear "2015" @default.
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