4-Amino-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-((Z)-propenyl)-1H-pyrimidin-2-one | 66270-35-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-Amino-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-((Z)-propenyl)-1H-pyrimidin-2-one
• 英文别名: 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-[(Z)-prop-1-enyl]pyrimidin-2-one；4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(Z)-prop-1-enyl]pyrimidin-2-one
• CAS: 66270-35-7
• 化学式: C₁₂H₁₇N₃O₄
• 分子量: 267.285
• InChiKey: KATMTGGBSHKNTC-JQQSAOSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5'-chloromercuri-2'-deoxycytidine 在 lithium tetrachloropalladate 、 RhCl(PPh₃)3 、 copper dichloride 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 4-Amino-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-((Z)-propenyl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity

  摘要：

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.

  DOI：

  10.1021/jm00363a009

文献信息

• NANOPARTICLE NUCLEIC ACID BINDING COMPOUND CONJUGATES FORMING I-MOTIFS
  申请人：Seela Frank

  公开号：US20100290992A1

  公开（公告）日：2010-11-18

  The present invention concerns the field of nanoparticle bioconjugates which form an i-motif or an i-motif related structure (compositions) without or with at least one further nucleic acid binding compound. The i-motif base pairs can be charged or non-charged. Their assembly can be controlled by the pH value or temperature. At least one of these nucleic acid binding compounds has to be attached at least to a nanoparticle. The methods provide compositions used for DNA driven programmable nanoparticle assemblies, electronic circuits, diagnostic detection tools, biosensors, memory storage devices, diagnostic devices for biomolecule sequencing and detection, drug delivery, application in tumour diagnostics and treatment, nanomachines, nanofabrication, nanocatalysis, nanoarrays, and nanoscaled enzyme reactors.

  本发明涉及纳米颗粒生物共轭物的领域，其形成了一个i-结构或与i-结构相关的结构（组成物），没有或至少有一种进一步的核酸结合化合物。i-结构碱基对可以带电或不带电。它们的组装可以通过pH值或温度进行控制。这些核酸结合化合物中至少有一种必须至少附着在一个纳米颗粒上。该方法提供了用于DNA驱动的可编程纳米颗粒组装、电子电路、诊断检测工具、生物传感器、存储器设备、用于生物分子测序和检测的诊断设备、药物传递、应用于肿瘤诊断和治疗、纳米机器、纳米制造、纳米催化、纳米阵列和纳米级酶反应器的组成物。
• US4267171A
  申请人：——

  公开号：US4267171A

  公开（公告）日：1981-05-12
• Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity
  作者：John Goodchild、Roderick A. Porter、Robert H. Raper、Iain S. Sim、Roger M. Upton、Julie Viney、Harry J. Wadsworth

  DOI：10.1021/jm00363a009

  日期：1983.9

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.