(+/-)-(1α,2β,4β)-4-<(2-amino-6-chloropyrimidin-4-yl)amino>-1,2-cyclopentanediol | 140438-64-8

• 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: (+/-)-(1α,2β,4β)-4-<(2-amino-6-chloropyrimidin-4-yl)amino>-1,2-cyclopentanediol
• 英文别名: (+/-)-(1α,2β,4β)-4-[(2-amino-6-chloropyrimidin-4-yl)amino]-1,2-cyclopentanediol
• CAS: 140438-64-8
• 化学式: C₉H₁₃ClN₄O₂
• 分子量: 244.681
• InChiKey: DBXDAPLTAGERTK-PHDIDXHHSA-N

物化性质

• 沸点：
  546.5±60.0 °C(Predicted)
• 密度：
  1.649±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.01
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  104.29
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(1α,2β,4β)-4-<(2-amino-6-chloropyrimidin-4-yl)amino>-1,2-cyclopentanediol 在 盐酸 、 氨 、 sodium acetate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 76.5h， 生成 (+/-)-(1α,2β,4β)-4-(2,6-diamino-9H-purin-9-yl)-1,2-cyclopentanediol
  参考文献：
  名称：

  (.+-.)-Carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties

  摘要：

  Beginning with 3-cyclopenten-1-ylamine hydrochloride, the 5'-nor derivatives of carbocyclic 2'-deoxyguanosine (2), 2'-deoxyadenosine (3), and 2,6-diaminopurine 2'-deoxyribofuranoside (4) have been prepared. These compounds were evaluated for antiviral potential versus herpes simplex virus, varicella-zoster virus, cytomegalovirus, vaccinia virus, vesicular stomatitis virus, and human immunodeficiency virus and found to lack activity. Also, compounds 2-4 were virtually nontoxic toward the host (human diploid fibroblast ESM and HEL) cells. These biological properties may be due to the inability of 2-4 to be phosphorylated to the requisite nucleotide level that is likely to be necessary for biological activity by correlation to carbocyclic 2'-deoxyguanosine (1), which possesses significant antiviral properties as a result of conversion to its 5'-triphosphate derivative.

  DOI：

  10.1021/jm00090a007
• 作为产物：
  描述：

  N-(3-环戊烯-1-基)苯甲酰胺 在 吡啶 、 盐酸 、 硫酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 水 、 正丁醇 为溶剂， 反应 74.0h， 生成 (+/-)-(1α,2β,4β)-4-<(2-amino-6-chloropyrimidin-4-yl)amino>-1,2-cyclopentanediol
  参考文献：
  名称：

  (.+-.)-Carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties

  摘要：

  Beginning with 3-cyclopenten-1-ylamine hydrochloride, the 5'-nor derivatives of carbocyclic 2'-deoxyguanosine (2), 2'-deoxyadenosine (3), and 2,6-diaminopurine 2'-deoxyribofuranoside (4) have been prepared. These compounds were evaluated for antiviral potential versus herpes simplex virus, varicella-zoster virus, cytomegalovirus, vaccinia virus, vesicular stomatitis virus, and human immunodeficiency virus and found to lack activity. Also, compounds 2-4 were virtually nontoxic toward the host (human diploid fibroblast ESM and HEL) cells. These biological properties may be due to the inability of 2-4 to be phosphorylated to the requisite nucleotide level that is likely to be necessary for biological activity by correlation to carbocyclic 2'-deoxyguanosine (1), which possesses significant antiviral properties as a result of conversion to its 5'-triphosphate derivative.

  DOI：

  10.1021/jm00090a007