(+/-)-2,5-diamino-4-<<5'α-<(benzyloxy)methyl>-4'β-(hydroxymethyl)cyclopent-2'-en-1'β-yl>amino>-6-chloropyridimine | 140440-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-2,5-diamino-4-<<5'α-<(benzyloxy)methyl>-4'β-(hydroxymethyl)cyclopent-2'-en-1'β-yl>amino>-6-chloropyridimine
• 英文别名: (+/-)-2,5-diamino-4-({5'α-[(benzyloxy)methyl]-4'β-(hydroxymethyl)cyclopent-2'-en-1'β-yl}amino)-6-chloropyridimine；[(1S,4R,5R)-4-[(2,5-diamino-6-chloropyrimidin-4-yl)amino]-5-(phenylmethoxymethyl)cyclopent-2-en-1-yl]methanol
• CAS: 140440-43-3
• 化学式: C₁₈H₂₂ClN₅O₂
• 分子量: 375.858
• InChiKey: UDVSDESMYBFFTE-MGPQQGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119.31
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (+/-)-2,5-diamino-4-<<5'α-<(benzyloxy)methyl>-4'β-(hydroxymethyl)cyclopent-2'-en-1'β-yl>amino>-6-chloropyridimine 在 盐酸 、 氢氧化钾 、 三氯化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (+/-)-9-<4'β,5'α-bis(hydroxymethyl)cyclopent-2'-en-1'β-yl>guanine
  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：

  (+/-)-2-amino-4-<<5'α-<(benzyloxy)methyl>-4'β-(hydroxymethyl)cyclopent-2'-en-1'β-yl>amino>-6-chloropyridimine 在 sodium acetate 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 9.0h， 生成 (+/-)-2,5-diamino-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