4(S)-(9H-purin-9-yl)tetrahydro-2(S)-furanmethanol | 141585-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4(S)-(9H-purin-9-yl)tetrahydro-2(S)-furanmethanol
• 英文别名: (2R-cis)-tetrahydro-4-(9H-purin-9-yl)-2-furanmethanol；[(2S,4S)-4-purin-9-yloxolan-2-yl]methanol
• CAS: 141585-90-2
• 化学式: C₁₀H₁₂N₄O₂
• 分子量: 220.231
• InChiKey: JKBHSTXXELWFTA-YUMQZZPRSA-N

物化性质

• 沸点：
  457.4±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 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：
  73.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4(S)-(9H-purin-9-yl)tetrahydro-2(S)-furanmethylacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以76.2%的产率得到4(S)-(9H-purin-9-yl)tetrahydro-2(S)-furanmethanol
  参考文献：
  名称：

  Synthesis and Conformational Studies of New Purine Isodideoxynucleosides

  摘要：

  The synthesis and NMR conformational correlations (preferred syn or anti) of new isomeric dideoxynucleosides of potential antiviral interest are described. These compounds are related to the potently active anti-HIV compound, (S,S)-isodideoxy-adenosine.

  DOI：

  10.1080/07328319608002371

文献信息

• Antiviral, metabolic, and pharmacokinetic properties of the isomeric dideoxynucleoside 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol
  作者：V Nair、M H St Clair、J E Reardon、H C Krasny、R J Hazen、M T Paff、L R Boone、M Tisdale、I Najera、R E Dornsife

  DOI：10.1128/aac.39.9.1993

  日期：1995.9

  IsoddA-resistant virus (eightfold-increased 50% inhibitory concentration) was selected in vitro by repeated passage of HIV-1 (HXB2) in the presence of increasing concentrations of IsoddA. The reverse transcriptase-coding region of the mutant virus contained a single base change resulting in a change at codon 184 from Met to Val. IsoddA was also active against hepatitis B virus (HBV) in vitro; however, it

  4（S）-（6-氨基-9H-嘌呤-9-基）四氢-2（S）-呋喃甲醇（IsoddA）是一类新型旋光异构二脱氧核苷中最抗病毒的成员从自然的1'位置转置为2'位置，并且绝对构型为（S，S）。IsoddA对人免疫缺陷病毒1型（HIV-1）（IIIB株），HIV-2（ZY株）和HIV-1临床分离株具有活性。该化合物与齐多夫定（3'-叠氮基-3'-脱氧胸苷），2'，3'-二脱氧肌苷或5-氟-2'-脱氧-3'-硫代胞苷的组合显示出对HIV的协同抑制作用。用对齐多夫定耐药的临床分离株观察到活性适度降低。通过在增加的IsoddA浓度下重复传播HIV-1（HXB2），在体外选择对IsoddA耐药的病毒（抑制浓度增加8倍）。突变病毒的逆转录酶编码区包含单个碱基变化，导致第184位密码子从Met变为Val。IsoddA在体外还具有抗乙型肝炎病毒（HBV）的活性；然而，它在体内HBV模型中缺乏实质的选择性活性。Is
• Synthesis and anti-HIV activity of isonucleosides
  作者：Donna M. Huryn、Barbara C. Sluboski、Steve Y. Tam、Manfred Weigele、Iain Sim、Barry D. Anderson、Hiroaki Mitsuya、Samuel Broder

  DOI：10.1021/jm00091a001

  日期：1992.6

  A series of isomeric 2',3'-dideoxynucleosides which contains a modified carbohydrate moiety has been prepared. This class of compounds was designed to mimic the activity of known anti-HIV dideoxynucleosides, while imparting enhanced chemical and enzymatic stability. Isonucleosides containing the standard heterocyclic bases (A, C, G, T) were synthesized via nucleophilic addition of the base to an isomeric sugar unit. Modified derivatives were generated by manipulation of the intact isonucleoside. Two of the compounds prepared, iso-ddA (1) and iso-ddG (6), exhibit significant and selective anti-HIV activity, as well as beneficial hydrolytic stability.