(+/-)-(1α,2β,4β)-4-<<2-amino-6-chloro-5<(4-chlorophenyl)-azo>pyrimidin-4-yl>amino>-1,2-cyclopentanediol | 140438-65-9

• 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-chloro-5<(4-chlorophenyl)-azo>pyrimidin-4-yl>amino>-1,2-cyclopentanediol
• 英文别名: (+/-)-(1α,2β,4β)-4-({2-amino-6-chloro-5[(4-chlorophenyl)-azo]pyrimidin-4-yl}amino)-1,2-cyclopentanediol；(1S,2S)-4-[[2-amino-6-chloro-5-[(4-chlorophenyl)diazenyl]pyrimidin-4-yl]amino]cyclopentane-1,2-diol
• CAS: 140438-65-9
• 化学式: C₁₅H₁₆Cl₂N₆O₂
• 分子量: 383.237
• InChiKey: DOLXUBYFHVHISW-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  129.01
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(1α,2β,4β)-4-<<2-amino-6-chloro-5<(4-chlorophenyl)-azo>pyrimidin-4-yl>amino>-1,2-cyclopentanediol 在 溶剂黄146 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以65%的产率得到(+/-)-(1α,2β,4β)-4-<(2,5-diamino-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
• 作为产物：
  描述：

  (+/-)-(1α,3α,4β)-N-<3,4-bis(acetyloxy)cyclopentenyl>benzamide 在 盐酸 、 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 水 、 正丁醇 为溶剂， 反应 75.0h， 生成 (+/-)-(1α,2β,4β)-4-<<2-amino-6-chloro-5<(4-chlorophenyl)-azo>pyrimidin-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