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Synthesis and Evaluation of Novel 6',6'-difluoro 5'-deoxycarbocyclic Phosphonic Acid Nucleosides as Antiviral Agents

Synthesis and Evaluation of Novel 6',6'-difluoro 5'-deoxycarbocyclic Phosphonic Acid Nucleosides as Antiviral Agents

Eunae Kim, Guang Huan Shen, Lien Kang, Joon Hee Hong

Nucleosides Nucleotides Nucleic Acids. 2013;32(7):396-410.

PMID: 23742064

Abstract:

The authors describe highly efficient synthetic routes for the preparation of novel 6',6'-difluoro 5'-deoxycarbocyclic phosphonic acid nucleosides from 1,4-dihydroxy-2-butene. The discovery that the 6'-fluorinated carbocyclic nucleoside (2, EC₅₀ = 0.16 μM) is a potent anti-HSV-1 agent led to the syntheses and biological evaluations of 6'-modified 5'-deoxyversions of carbocyclic phosphonate nucleosides. The synthesized nucleoside analogues 15, 18, 22, and 25 were tested for anti-HIV activity and for cytotoxicity. However, none of them showed significant anti-HIV-1 activity or cytotoxicity at concentrations up to 100 μM.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4721226	(6-Phosphonohexyl)phosphonic acid		4721-22-6	Price

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