(1S,2R,3R)-3-(2,6-diaminopurin-9-yl)-2-(hydroxymethyl)cyclobutanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (1S,2R,3R)-3-(2,6-diaminopurin-9-yl)-2-(hydroxymethyl)cyclobutanol
• 英文别名: (1S,2R,3R)-3-(2,6-diaminopurin-9-yl)-2-(hydroxymethyl)cyclobutan-1-ol
• 化学式: C₁₀H₁₄N₆O₂
• 分子量: 250.26
• InChiKey: ITWVNEGKASNHFP-JKUQZMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氨基-6-氯嘌呤 在 盐酸 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 98.83h， 生成 (1S,2R,3R)-3-(2,6-diaminopurin-9-yl)-2-(hydroxymethyl)cyclobutanol
  参考文献：
  名称：

  Carbocyclic Oxetanocins Lacking the C-3‘ Methylene

  摘要：

  Using the observation that the side effects of aristeromycin (carbocyclic adenosine) were reduced by removing the methylene at the center in aristeromycin where phosphorylation occurs, derivatives of carbocyclic oxetanocin A (4a), oxetanocin G (4b), and 2-aminooxetanocin A (16) lacking the 3'-methylene have been prepared in racemic form. The only viruses for which an appreciable inhibitory effect of the compounds (minimum inhibitory concentration ranging from 1 to 40 mu g/mL) was noted were herpes simplex virus type 1 (HSV-1) and varicella-zoster virus (VZV). However, when directly compared for their antiviral potency against HSV-1 with their parents oxetanocin A and oxetanocin G, compounds 4a and 4b proved clearly less active.

  DOI：

  10.1021/jm960770e

文献信息

• Carbocyclic Oxetanocins Lacking the C-3‘ Methylene
  作者：Jayu Wu、Stewart W. Schneller、Katherine L. Seley、Robert Snoeck、Graciela Andrei、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm960770e

  日期：1997.4.1

  Using the observation that the side effects of aristeromycin (carbocyclic adenosine) were reduced by removing the methylene at the center in aristeromycin where phosphorylation occurs, derivatives of carbocyclic oxetanocin A (4a), oxetanocin G (4b), and 2-aminooxetanocin A (16) lacking the 3'-methylene have been prepared in racemic form. The only viruses for which an appreciable inhibitory effect of the compounds (minimum inhibitory concentration ranging from 1 to 40 mu g/mL) was noted were herpes simplex virus type 1 (HSV-1) and varicella-zoster virus (VZV). However, when directly compared for their antiviral potency against HSV-1 with their parents oxetanocin A and oxetanocin G, compounds 4a and 4b proved clearly less active.