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Prodrugs of 9-(beta-D-arabinofuranosyl)adenine 2. Synthesis and evaluation of a number of 2',3'- and 3',5'-di-O-acyl derivatives.

作者信息

Baker D C, Haskell T H, Putt S R, Sloan B J

出版信息

J Med Chem. 1979 Mar;22(3):273-9. doi: 10.1021/jm00189a011.

DOI:10.1021/jm00189a011
PMID:218013
Abstract

A number of 2',3'- and 3',5'-di-O-acyl derivatives of 9-beta-D-arabinofuranosyladenine (1) were prepared and evaluated as antivirals. These compounds, designed as prodrugs of 1, offer a range of solubilities and lipophilicities, as well as a resistance to adenosine deaminase, that render some as being attractive as possibly useful antiviral agents. Of particular note is 9-(2,3-di-O-acetyl-beta-D-arabinofuranosyl)adenine that was found to be effective as a topical agent in a guinea pig model of genital herpes.

摘要

相似文献

1
Prodrugs of 9-(beta-D-arabinofuranosyl)adenine 2. Synthesis and evaluation of a number of 2',3'- and 3',5'-di-O-acyl derivatives.
J Med Chem. 1979 Mar;22(3):273-9. doi: 10.1021/jm00189a011.
2
Prodrugs of 9-beta-D-arabinofuranosyladenine. 1. Synthesis and evaluation of some 5'-(O-acyl) derivatives.9-β-D-阿拉伯呋喃糖基腺嘌呤的前药。1. 一些5'-(O-酰基)衍生物的合成与评价。
J Med Chem. 1978 Dec;21(12):1218-21. doi: 10.1021/jm00210a009.
3
Synthesis and evaluation of a series of 2'-O-acyl derivatives of 9-beta-D-arabinofuranosyladenine as antiherpes agents.一系列9-β-D-阿拉伯呋喃糖基腺嘌呤的2'-O-酰基衍生物作为抗疱疹剂的合成与评价
J Med Chem. 1984 Mar;27(3):270-4. doi: 10.1021/jm00369a007.
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J Med Chem. 1977 Mar;20(3):401-4. doi: 10.1021/jm00213a017.
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Synthesis of N6- or 8-substituted 9-(beta-D-arabinofuranosyl)-adenines and their antiviral activities against herpes simplex and vaccinia viruses.N6-或8-取代的9-(β-D-阿拉伯呋喃糖基)腺嘌呤的合成及其对单纯疱疹病毒和痘苗病毒的抗病毒活性。
Chem Pharm Bull (Tokyo). 1977 Oct;25(10):2482-9. doi: 10.1248/cpb.25.2482.
6
Anti-herpes activity of the adenine arabinoside analog, 2'-azido-2'-deoxy-beta-D-arabinofuranosyladenine.腺嘌呤阿拉伯糖苷类似物2'-叠氮基-2'-脱氧-β-D-阿拉伯呋喃糖基腺嘌呤的抗疱疹活性
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Influence of 1-dodecylazacycloheptan-2-one (Azone) on the topical therapy of cutaneous herpes simplex virus type 1 infection in hairless mice with 2',3'-di-O-acetyl-9-beta-D-arabinofuranosyladenine and 5'-O-valeryl-9-beta-D-arabinofuranosyladenine.1-十二烷基氮杂环庚烷-2-酮（氮酮）对无毛小鼠皮肤单纯疱疹病毒1型感染采用2'，3'-二-O-乙酰基-9-β-D-阿拉伯呋喃糖基腺嘌呤和5'-O-戊酰基-9-β-D-阿拉伯呋喃糖基腺嘌呤进行局部治疗的影响。
J Pharm Sci. 1985 Nov;74(11):1157-61. doi: 10.1002/jps.2600741105.
8
1-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-5-ethyluracil. A highly selective antiherpes simplex agent.1-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）-5-乙基尿嘧啶。一种高度选择性的抗单纯疱疹病毒剂。
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J Med Chem. 1982 Jan;25(1):96-8. doi: 10.1021/jm00343a021.
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Activity of (+)-cyclaradine (Sch 31172) against herpes simplex virus in vitro and in vivo.（+）-环拉定（Sch 31172）在体外和体内对单纯疱疹病毒的活性。
Antimicrob Agents Chemother. 1987 Jan;31(1):21-6. doi: 10.1128/AAC.31.1.21.

引用本文的文献

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5'-O-D-valyl ara A, a potential prodrug for improving oral bioavailability of the antiviral agent vidarabine.5'-O-D-缬氨酰阿糖腺苷，一种用于提高抗病毒药物阿糖腺苷口服生物利用度的潜在前体药物。
Nucleosides Nucleotides Nucleic Acids. 2009;28(1):43-55. doi: 10.1080/15257770802581757.
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Design and synthesis of vidarabine prodrugs as antiviral agents.设计和合成阿糖腺苷前药作为抗病毒药物。
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3
Evaluation of prodrugs of 9-beta-D-arabinofuranosyladenine for therapeutic efficacy in the topical treatment of genital herpesvirus infections in guinea pigs.
9-β-D-阿拉伯呋喃糖基腺嘌呤前药对豚鼠生殖器疱疹病毒感染局部治疗的疗效评估。
Antimicrob Agents Chemother. 1983 Nov;24(5):706-12. doi: 10.1128/AAC.24.5.706.
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Selection of a derivative of the antiviral agent 9-[(1,3-dihydroxy-2-propoxy)-methyl]guanine (DHPG) with improved oral absorption.
Pharm Res. 1987 Apr;4(2):120-5. doi: 10.1023/a:1016462801968.
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The synthesis of branched-chain 3'-C-cyanomethyl-2',3'-dideoxy sugar nucleosides of adenine as potential inhibitors of the human immunodeficiency virus.作为人类免疫缺陷病毒潜在抑制剂的腺嘌呤支链3'-C-氰甲基-2',3'-二脱氧糖核苷的合成。
Nucleic Acids Res. 1989 Oct 11;17(19):7663-70. doi: 10.1093/nar/17.19.7663.