5-(3-propenyl)-2'-deoxycytidine | 66270-31-3

• 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: 5-(3-propenyl)-2'-deoxycytidine
• 英文别名: 5-allyl-2'-deoxy-cytidine；5-Allyl-2'-deoxycytidin；4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-prop-2-enylpyrimidin-2-one
• CAS: 66270-31-3
• 化学式: C₁₂H₁₇N₃O₄
• 分子量: 267.285
• InChiKey: RFMWNCXQGFGIQN-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  4
• 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

• 作为反应物：
  描述：

  5-(3-propenyl)-2'-deoxycytidine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以94%的产率得到5-propyl-2'-deoxy-cytidine
  参考文献：
  名称：

  Hassan, M., Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 8, p. 627 - 630

  摘要：

  DOI：
• 作为产物：
  描述：

  丙烯酰碘 、 2'-脱氧胞嘧啶核苷 以 水 、 乙腈 为溶剂， 反应 24.0h， 以38%的产率得到5-(3-propenyl)-2'-deoxycytidine
  参考文献：
  名称：

  Hassan, M., Bulletin des Societes Chimiques Belges, 1991, vol. 100, # 8, p. 627 - 630

  摘要：

  DOI：

文献信息

• 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.
• HASSAN, M. E., BULL. SOC. CHIM. BELG., 100,(1991) N, C. 627-630
  作者：HASSAN, M. E.

  DOI：——

  日期：——
• EP0135587A4
  申请人：——

  公开号：EP0135587A4

  公开（公告）日：1986-04-02
• DEFINED SEQUENCE SINGLE STRAND OLIGONUCLEOTIDES INCORPORATING REPORTER GROUPS, PROCESS FOR THE CHEMICAL SYNTHESIS THEREOF, AND NUCLEOSIDES USEFUL IN SUCH SYNTHESIS
  申请人：MOLECULAR BIOSYSTEMS, INC.

  公开号：EP0135587A1

  公开（公告）日：1985-04-03
• US4267171A
  申请人：——

  公开号：US4267171A

  公开（公告）日：1981-05-12