isoguanosine | 50613-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isoguanosine
• 英文别名: 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-purin-2-one
• CAS: 50613-36-0
• 化学式: C₁₀H₁₃N₅O₅
• 分子量: 283.244
• InChiKey: SVBCHYLCFKRZQD-UUOKFMHZSA-N

物化性质

• 沸点：
  784.6±70.0 °C(Predicted)
• 密度：
  2.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isoguanosine 在 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 6-amino-5',9-anhydro-3-(2,3-O-isopropylidene-β-D-ribofuranosyl)-9H-purine-2(3H)-one
  参考文献：
  名称：

  Synthesis and Biological Activity of 5′,9-Anhydro-3-Purine-ISONucleosides as Potential Anti-Hepatitis C Virus Agents

  摘要：

  In order to study structure-activity relationships among the derivatives and congeners of 5',9-anhydro-3-(beta-D-ribofuranosyl)xanthine for anti-hepatitis C virus activity, a series of 5',9-anhydro-purine-isonucleosides with a substituent (s) at 6- or/and 8-position of the purine moiety were synthesized, and their anti-hepatitis C virus activity and cytotoxicity were evaluated and discussed.

  DOI：

  10.1080/15257770601052307
• 作为产物：
  描述：

  5-(3-Benzoyl-thioureido)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-imidazole-4-carboxylic acid amide 在 氨 、 N,N'-二环己基碳二亚胺 作用下， 以 ammonium hydroxide 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 isoguanosine
  参考文献：
  名称：

  一种新型，高效的异鸟苷合成

  摘要：

  异鸟苷（）是通过一锅反应合成的，其中一锅反应涉及将5-氨基-1-（β-D-呋喃呋喃糖基）咪唑-4-羧酰胺（）与苯甲酰基异硫氰酸酯缩合，然后用DCC修饰5-（-）生成的硫脲衍生物。然后将N 1-苯甲酰氨基甲酰基）氨基咪唑-4-腈（）与乙醇氨水环化，得到异鸟苷，产率为68％。

  DOI：

  10.1016/s0040-4039(00)96067-2

文献信息

• 5,6-Diaminocytidine, a Versatile Synthon for Pyrimidine-Based Bicyclic Nucleosides
  作者：Kallanthottathil G. Rajeev、Arthur D. Broom

  DOI：10.1021/ol0064765

  日期：2000.11.1

  This communication describes a convenient, facile, and high-yield synthesis of 3-(beta-D-ribofuranosyl)isoguanine and its 8-methyl derivative, as well as nucleoside analogues of pteridines, from a common precursor, 5,6-diaminocytidine. 5,6-Diamino-2',3', 5'-tri-O-benzoylcytidine was synthesized from 4, 6-diamino-2-oxopyrimidine in three steps.

  该文描述了从常见的前体5,6-二氨基胞苷中合成3-（β-D-呋喃核糖基）异鸟嘌呤及其8-甲基衍生物以及蝶啶的核苷类似物的便捷，简便且高收率的合成方法。由4，6-二氨基-2-氧代嘧啶经三个步骤合成5，6-二氨基-2′，3′，5′-三-O-苯甲酰基胞苷。
• A novel and efficient synthesis of isoguanosine
  作者：Chern Ji-Wang、Lee Horng-Yuh、Huang Min、Shish Fang-Jy

  DOI：10.1016/s0040-4039(00)96067-2

  日期：1987.1

  Isoguanosine () was synthesized by a one-pot reaction involving acondensation of 5-amino- 1-(β-D-ribofuranosyl)imidazole-4-carboxamide () with benzoyl isothiocyanate, treatment of the resulting thiourea derivative with DCC furnished 5-(N1-benzoylcarbamoyl)aminoimidazole- 4-carbonitrile () which was then annulated with ethanolic ammonia to afford isoguanosine in a 68% yield from .

  异鸟苷（）是通过一锅反应合成的，其中一锅反应涉及将5-氨基-1-（β-D-呋喃呋喃糖基）咪唑-4-羧酰胺（）与苯甲酰基异硫氰酸酯缩合，然后用DCC修饰5-（-）生成的硫脲衍生物。然后将N 1-苯甲酰氨基甲酰基）氨基咪唑-4-腈（）与乙醇氨水环化，得到异鸟苷，产率为68％。
• Synthesis and Biological Activity of 5′,9-Anhydro<i>-</i>3-Purine-<i>ISO</i>Nucleosides as Potential Anti-Hepatitis C Virus Agents
  作者：Byoung-Kwon Chun、Peiyuan Wang、Abdalla Hassan、Jinfa Du、Phillip M. Tharnish、Eisuke Murakami、Lieven Stuyver、Michael J. Otto、Raymond F. Schinazi、Kyoichi A. Watanabe

  DOI：10.1080/15257770601052307

  日期：2007.1

  In order to study structure-activity relationships among the derivatives and congeners of 5',9-anhydro-3-(beta-D-ribofuranosyl)xanthine for anti-hepatitis C virus activity, a series of 5',9-anhydro-purine-isonucleosides with a substituent (s) at 6- or/and 8-position of the purine moiety were synthesized, and their anti-hepatitis C virus activity and cytotoxicity were evaluated and discussed.