(-)-(1R,3S)-1-[(3-hydroxymethyl-1,2,2-trimethyl)cyclopentylmethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione | 443301-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (-)-(1R,3S)-1-[(3-hydroxymethyl-1,2,2-trimethyl)cyclopentylmethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• 英文别名: 1-(((1R,3S)-3-(hydroxymethyl)-1,2,2-trimethylcyclopentyl)methyl)pyrimidine-2,4(1H,3H)-dione；1-[[(1R,3S)-3-(hydroxymethyl)-1,2,2-trimethyl-cyclopentyl]methyl]pyrimidine-2,4-dione；1-[[(1R,3S)-3-(hydroxymethyl)-1,2,2-trimethylcyclopentyl]methyl]pyrimidine-2,4-dione
• CAS: 443301-06-2
• 化学式: C₁₄H₂₂N₂O₃
• 分子量: 266.34
• InChiKey: RLKSFVIACANWCX-YGRLFVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1R,3S)-1-[(3-hydroxymethyl-1,2,2-trimethyl)cyclopentylmethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione 在 碘 、 硝酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以67%的产率得到(-)-(1R,3S)-1-[(3-hydroxymethyl-1,2,2-trimethyl)cyclopentylmethyl]-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione
  参考文献：
  名称：

  SYNTHESIS, ANTIVIRAL AND CYTOSTATIC ACTIVITIES, OF CARBOCYCLIC NUCLEOSIDES INCORPORATING A MODIFIED CYCLOPENTANE RING. IV. ADENOSINE AND URIDINE ANALOGUES

  摘要：

  Eight new carbocyclic nucleosides were prepared by mounting a purine (compounds 8-10), 8-azapurine (12 and 13) or pyrimidine (15, 16 and 17b) on the amino group of (1S,3R)-3-aminomethyl-2,2,3-trimethyl-cyclopentylmethanol (6). All the compounds were evaluated as antiviral and antitumor agents in a variety of assay systems. Only compound 8 showed any cytostatic activity against the tumor cell lines examined.

  DOI：

  10.1081/ncn-120003289
• 作为产物：
  描述：

  (+)-(1R,3S)-N-[(3-hydroxymethyl-1,2,2-trimethyl)cyclopentylmethyl]-N'-(3-ethoxypropenoyl)urea 在 ammonium hydroxide 作用下， 反应 28.0h， 以70%的产率得到(-)-(1R,3S)-1-[(3-hydroxymethyl-1,2,2-trimethyl)cyclopentylmethyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
  参考文献：
  名称：

  SYNTHESIS, ANTIVIRAL AND CYTOSTATIC ACTIVITIES, OF CARBOCYCLIC NUCLEOSIDES INCORPORATING A MODIFIED CYCLOPENTANE RING. IV. ADENOSINE AND URIDINE ANALOGUES

  摘要：

  Eight new carbocyclic nucleosides were prepared by mounting a purine (compounds 8-10), 8-azapurine (12 and 13) or pyrimidine (15, 16 and 17b) on the amino group of (1S,3R)-3-aminomethyl-2,2,3-trimethyl-cyclopentylmethanol (6). All the compounds were evaluated as antiviral and antitumor agents in a variety of assay systems. Only compound 8 showed any cytostatic activity against the tumor cell lines examined.

  DOI：

  10.1081/ncn-120003289