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[1,2,4-三唑核苷:化学酶法合成的潜力与局限]

[Nucleosides of 1,2,4-triazole: potentialities and restrictions of chemo-enzymatic method for synthesis].

作者信息

Konstantinova I D, Chudinov M V, Fateev I V, Matveev A V, Zhurilo N I, Shvets V I, Miroshnikov A I

出版信息

Bioorg Khim. 2013 Jan-Feb;39(1):61-80. doi: 10.1134/s1068162013010056.

DOI:10.1134/s1068162013010056
PMID:23844508
Abstract

The potentialities and restrictions of chemoenzymatic approach to the synthesis of new structural analogues of antiviral drug Ribavirin (1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide) have been determined. Syntheses of various amides of 1H-1,2,4-triazole-3-carboxylic acid and its 5-substituted analogues, prospective substrates of purine nucleoside phosphorylase (PNP), have been reported. The comparative effectiveness of the methods for obtaining amides aforementioned and also the methods for introducing functional groups to the C5 position of the heterocyclic system has been studied. New Ribavirin analogues bearing various substituents in the carboxamide group have been synthesized. The biotechnological method for the preparation of 1-beta-D-ribofuranosyl- 1,2,4-triazole-3-carbonitrile used as the intermediate in the synthesis of Viramidine, a contemporary Ribavirin analogue, has been developed.

摘要

已确定化学酶法合成抗病毒药物利巴韦林(1-β-D-呋喃核糖基-1,2,4-三唑-3-甲酰胺)新结构类似物的潜力和限制。已报道了1H-1,2,4-三唑-3-羧酸及其5-取代类似物(嘌呤核苷磷酸化酶(PNP)的潜在底物)的各种酰胺的合成。研究了上述获得酰胺的方法以及将官能团引入杂环系统C5位的方法的相对有效性。已合成了在甲酰胺基团中带有各种取代基的新型利巴韦林类似物。已开发出用于制备1-β-D-呋喃核糖基-1,2,4-三唑-3-腈的生物技术方法,该化合物用作当代利巴韦林类似物维拉美定合成中的中间体。

相似文献

1
[Nucleosides of 1,2,4-triazole: potentialities and restrictions of chemo-enzymatic method for synthesis].[1,2,4-三唑核苷:化学酶法合成的潜力与局限]
Bioorg Khim. 2013 Jan-Feb;39(1):61-80. doi: 10.1134/s1068162013010056.
2
Synthesis of Substituted 1,2,4-Triazole-3-Thione Nucleosides Using Purine Nucleoside Phosphorylase.嘌呤核苷磷酸化酶在取代 1,2,4-三唑-3-硫酮核苷合成中的应用
Biomolecules. 2024 Jun 24;14(7):745. doi: 10.3390/biom14070745.
3
Synthesis of 1-(4-thio-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxamide.1-(4-硫代-β-D-呋喃核糖基)-1,2,4-三唑-3-甲酰胺的合成
J Med Chem. 1976 Jun;19(6):841-2. doi: 10.1021/jm00228a022.
4
Synthesis and evaluation of 5-amino-1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine and certain related nucleosides as inhibitors of purine nucleoside phosphorylase.5-氨基-1-β-D-呋喃核糖基-1,2,4-三唑-3-甲脒及某些相关核苷作为嘌呤核苷磷酸化酶抑制剂的合成与评价
J Med Chem. 1988 Feb;31(2):330-5. doi: 10.1021/jm00397a010.
5
Synthesis and antiviral acticity of some phosphates of the broad-spectrum antiviral nucleoside, 1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide (ribavirin).广谱抗病毒核苷1-β-D-呋喃核糖基-1,2,4-三唑-3-甲酰胺(利巴韦林)的某些磷酸盐的合成与抗病毒活性
J Med Chem. 1978 Aug;21(8):742-6. doi: 10.1021/jm00206a005.
6
[Biotechnological synthesis of ribavirin. Effect of ribavirin and its various combinations on the reproduction of Vaccinia virus].[利巴韦林的生物技术合成。利巴韦林及其各种组合对痘苗病毒繁殖的影响]
Bioorg Khim. 2004 Nov-Dec;30(6):613-20. doi: 10.1023/b:rubi.0000049772.18675.34.
7
Synthesis and determination of antiviral activity of the 2'(3')-O-methyl derivatives of ribavirin (1-beta-D-ribofuranosyl-1,2,4-triazole-3-carboxamide).利巴韦林(1-β-D-呋喃核糖基-1,2,4-三唑-3-甲酰胺)的2'(3')-O-甲基衍生物的合成及其抗病毒活性的测定
J Med Chem. 1977 Oct;20(10):1354-6. doi: 10.1021/jm00220a027.
8
Synthesis of 5-ethynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (isosteric to EICAR) and its derivatives.5-乙炔基-1-β-D-呋喃核糖基-1H-[1,2,3]三唑-4-羧酸酰胺(与EICAR等排)及其衍生物的合成。
Nucleic Acids Symp Ser (Oxf). 2008(52):585-6. doi: 10.1093/nass/nrn296.
9
Synthesis of homo-N-nucleoside with 1,2,4-triazole-3-carboxamide.含1,2,4-三唑-3-甲酰胺的同型N-核苷的合成。
Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):979-81. doi: 10.1081/ncn-200059368.
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Synthesis of 1,2,4-triazole C-nucleosides from hydrazonyl chlorides and nitriles.由酰肼氯化物和腈类化合物合成1,2,4-三唑C-核苷。
Nucleosides Nucleotides Nucleic Acids. 2007;26(1):37-43. doi: 10.1080/15257770601052265.

引用本文的文献

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Expanding the chemical space of 3(5)-functionalized 1,2,4-triazoles.拓展3(5)-官能化1,2,4-三唑的化学空间。
Chem Heterocycl Compd (N Y). 2022;58(2-3):116-128. doi: 10.1007/s10593-022-03064-z. Epub 2022 Mar 23.
2
Nucleoside Analogs with Fleximer Nucleobase.具有柔性核碱基的核苷类似物。
Chem Heterocycl Compd (N Y). 2020;56(6):636-643. doi: 10.1007/s10593-020-02713-5. Epub 2020 Jul 16.