5-膦酰基-戊-2-烯-1-基核苷的合成：一类新型的抗病毒无环核苷膦酸酯。
Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: a new class of antiviral acyclic nucleoside phosphonates.
作者信息
Choo Hyunah, Beadle James R, Chong Youhoon, Trahan Julissa, Hostetler Karl Y
机构信息
Department of Medicine, Division of Infectious Disease, University of California, San Diego, La Jolla, CA 92093-0676, USA.
出版信息
Bioorg Med Chem. 2007 Feb 15;15(4):1771-9. doi: 10.1016/j.bmc.2006.11.038. Epub 2006 Nov 30.
Abstract
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.
摘要
一类新的无环核苷膦酸酯，即5-膦酰基-戊-2-烯-1-基核苷及其十六烷氧基丙酯，由丁炔-1-醇合成。仅十六烷氧基丙酯在体外对1型单纯疱疹病毒显示出抗病毒活性。十六烷氧基丙基1-(5-膦酰基-戊-2-烯-1-基)-胸腺嘧啶是合成核苷酸中活性最高且选择性最强的化合物，其半数有效浓度（EC50）值为0.90微摩尔。
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1
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J Biol Chem. 2006 Jun 30;281(26):18193-200. doi: 10.1074/jbc.M602414200. Epub 2006 Apr 24.
2
Intracellular uptake of thymidine and antiherpetic drugs for thymidine kinase-deficient mutants of herpes simplex virus type 1.
Antiviral Res. 2006 Jul;70(3):93-104. doi: 10.1016/j.antiviral.2006.01.010. Epub 2006 Feb 20.
3
Antiviral therapies in children: has their time arrived?
Pediatr Clin North Am. 2005 Jun;52(3):837-67, vii. doi: 10.1016/j.pcl.2005.02.006.
4
New approaches toward anti-HIV chemotherapy.
J Med Chem. 2005 Mar 10;48(5):1297-313. doi: 10.1021/jm040158k.
5
Comparison of the antiviral activities of alkoxyalkyl and alkyl esters of cidofovir against human and murine cytomegalovirus replication in vitro.
Antimicrob Agents Chemother. 2005 Feb;49(2):656-62. doi: 10.1128/AAC.49.2.656-662.2005.
6
Oral treatment of murine cytomegalovirus infections with ether lipid esters of cidofovir.
Antimicrob Agents Chemother. 2004 Sep;48(9):3516-22. doi: 10.1128/AAC.48.9.3516-3522.2004.
7
Antiviral drugs in current clinical use.
J Clin Virol. 2004 Jun;30(2):115-33. doi: 10.1016/j.jcv.2004.02.009.
8
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9
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