7-syn-<(benzyloxy)methyl>-2-azabicyclo<2.2.1>hept-5-en-3-one | 140440-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 7-syn-<(benzyloxy)methyl>-2-azabicyclo<2.2.1>hept-5-en-3-one
• 英文别名: 7-syn-[(benzyloxy)methyl]-2-azabicyclo[2.2.1]hept-5-en-3-one
• CAS: 140440-30-8
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: ALGJEJQROOOCAY-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7-syn-<(benzyloxy)methyl>-2-azabicyclo<2.2.1>hept-5-en-3-one 在 氢氧化钾 、 sodium tetrahydroborate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 74.0h， 生成 (+/-)-2-amino-4-<<5'α-<(benzyloxy)methyl>-4'β-(hydroxymethyl)cyclopent-2'-en-1'β-yl>amino>-6-chloropyridimine
  参考文献：
  名称：

  Synthesis and anti-HIV activity of 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine

  摘要：

  The synthesis and in vitro anti-HIV activity of two new racemic nucleoside analogues are described; namely, 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (12) and its guanine analogue 18. While the latter (18) showed no activity, the therapeutic index of the former (12) was 200 and comparable to that (400) of carbovir. One enantiomer of 12 may be viewed as an analogue of carbocyclic oxetanocin and the other as an analogue of carbovir. Hence, these results indicate that one or both of the individual enantiomers of 12 could serve as candidates or lead compounds for the development of anti-AIDS agents.

  DOI：

  10.1021/jm00088a026
• 作为产物：
  描述：

  4-甲苯磺酰氰 、 (苄氧基甲基)环戊-2,4-二烯 以 乙醚 为溶剂， 反应 12.0h， 以17%的产率得到7-syn-<(benzyloxy)methyl>-2-azabicyclo<2.2.1>hept-5-en-3-one
  参考文献：
  名称：

  Synthesis and anti-HIV activity of 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine

  摘要：

  The synthesis and in vitro anti-HIV activity of two new racemic nucleoside analogues are described; namely, 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (12) and its guanine analogue 18. While the latter (18) showed no activity, the therapeutic index of the former (12) was 200 and comparable to that (400) of carbovir. One enantiomer of 12 may be viewed as an analogue of carbocyclic oxetanocin and the other as an analogue of carbovir. Hence, these results indicate that one or both of the individual enantiomers of 12 could serve as candidates or lead compounds for the development of anti-AIDS agents.

  DOI：

  10.1021/jm00088a026