(+/-)-1-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]cytosine | 1160714-38-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (+/-)-1-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]cytosine
• 英文别名: 4-Amino-1-[4,4-bis(hydroxymethyl)-5-methylene-cyclopent-2-en-1-yl]pyrimidin-2-one；4-amino-1-[4,4-bis(hydroxymethyl)-5-methylidenecyclopent-2-en-1-yl]pyrimidin-2-one
• CAS: 1160714-38-4
• 化学式: C₁₂H₁₅N₃O₃
• 分子量: 249.269
• InChiKey: NIVCMUXTOMRYGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  99.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+/-)-1-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]-N(4)-benzoylcytosine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以70%的产率得到(+/-)-1-[4,4-bis(hydroxymethyl)-5-methylenecyclopent-2-enyl]cytosine
  参考文献：
  名称：

  Novel Synthesis and Anti-HIV Activity of 4′-Branched Exomethylene Carbocyclic Nucleosides Using a Ring-Closing Metathesis of Triene

  摘要：

  The exomethylene of 6 was successfully constructed from the aldehyde 5 using Eschenmoser's reagents. A triene compound 7 was cyclized successfully using Grubbs' II catalyst to give an exomethylene carbocycle nucleus for the target compound. A Mitsunobu reaction was successfully used to condense the natural bases (adenine, thymine, uracil, and cytosine). The synthesized cytosine analogue 20 showed moderate anti-HIV activity (EC50 = 10.67 M).

  DOI：

  10.1080/15257770802458246

文献信息

• Novel Synthesis and Anti-HIV Activity of 4′-Branched Exomethylene Carbocyclic Nucleosides Using a Ring-Closing Metathesis of Triene
  作者：Hua Li、Jin Cheol Yoo、Joon Hee Hong

  DOI：10.1080/15257770802458246

  日期：2008.11.13

  The exomethylene of 6 was successfully constructed from the aldehyde 5 using Eschenmoser's reagents. A triene compound 7 was cyclized successfully using Grubbs' II catalyst to give an exomethylene carbocycle nucleus for the target compound. A Mitsunobu reaction was successfully used to condense the natural bases (adenine, thymine, uracil, and cytosine). The synthesized cytosine analogue 20 showed moderate anti-HIV activity (EC50 = 10.67 M).