+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: a new class of antiviral acyclic nucleoside phosphonates



Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: a new class of antiviral acyclic nucleoside phosphonates



Bioorganic and Medicinal Chemistry 15(4): 1771-1779



A new class of acyclic nucleoside phosphonates, the 5-phosphono-pent-2-en-1-yl nucleosides and their hexadecyloxypropyl esters, were synthesized from butyn-1-ol. Only the hexadecyloxypropyl esters showed antiviral activity against herpes simplex virus type 1, in vitro. Hexadecyloxypropyl 1-(5-phosphono-pent-2-en-1-yl)-thymine was the most active and selective compound among the synthesized nucleotides with an EC50 value of 0.90 microM.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 013020361

Download citation: RISBibTeXText

PMID: 17166725

DOI: 10.1016/j.bmc.2006.11.038


Related references

Efficient synthesis and biological properties of the 2-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates. Collection of Czechoslovak Chemical Communications 76(10): 1187-1198, 2011

Synthesis and antiviral activities of hexadecyloxypropyl prodrugs of acyclic nucleoside phosphonates containing guanine or hypoxanthine and a (S)-HPMP or PEE acyclic moiety. European Journal of Medicinal Chemistry 55: 307-314, 2013

6-(2-phosphonomethoxy)alkoxy)-2,4-diaminopyrimidines: A new class of acyclic pyrimidine nucleoside phosphonates with antiviral activity. Nucleosides Nucleotides and Nucleic Acids 23(8-9): 1321-1327, 2004

6-[2-phosphonomethoxy)alkoxy]-2,4-diaminopyrimidines: a new class of acyclic pyrimidine nucleoside phosphonates with antiviral activity. Nucleosides, Nucleotides and Nucleic Acids 23(8-9): 1321-1327, 2004

New prodrugs of two pyrimidine acyclic nucleoside phosphonates: Synthesis and antiviral activity. Bioorganic and Medicinal Chemistry 25(17): 4637-4648, 2017

Antiviral activities of novel 5-phosphono-pent-2-en-1-yl nucleosides and their alkoxyalkyl phosphonoesters. Antimicrobial Agents and ChemoTherapy 51(2): 611-615, 2006

Versatile synthesis of oxime-containing acyclic nucleoside phosphonates--synthetic solutions and antiviral activity. Organic and Biomolecular Chemistry 13(44): 10946-10956, 2016

Synthesis and antiviral evaluation of alkoxyalkyl esters of acyclic purine and pyrimidine nucleoside phosphonates against HIV-1 in vitro. Antiviral Research 72(1): 10-19, 2006

Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: efficient synthesis and antiviral activity. Bioorganic and Medicinal Chemistry 19(15): 4445-4453, 2011

Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: synthesis, antiviral activity and decomposition study. European Journal of Medicinal Chemistry 63: 869-881, 2013

A new class of acyclic nucleoside phosphonates Synthesis and biological activity of 9- aziridin-1-ylmethylguanine. Nucleosides Nucleotides & Nucleic Acids 21(10): 619-635, 2002

Bifunctional Acyclic Nucleoside Phosphonates: 2. Symmetrical 2-{[Bis(phosphono)methoxy]methyl}ethyl Derivatives of Purines and Pyrimidines. Collection of Czechoslovak Chemical Communications 72(7): 965-983, 2007

A new class of acyclic nucleoside phosphonates: Synthesis and biological activity of 9-(((phosphonomethyl)aziridin-1-yl)methyl)guanine (PMAMG) and analogues. Nucleosides Nucleotides and Nucleic Acids 21(10): 619-635, 2002

A new class of acyclic nucleoside phosphonates: synthesis and biological activity of 9-[[(phosphonomethyl)aziridin-1-yl]methyl]guanine (PMAMG) and analogues. Nucleosides, Nucleotides and Nucleic Acids 21(10): 619-635, 2002

Antiviral acyclic nucleoside phosphonates structure activity studies. Antiviral Research 71(2-3): 248-253, 2006