6-amino-2-(butylamino)-9-[[3-(chloromethyl)phenyl]methyl]-7H-purin-8-one | 1421583-19-8

• 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: 6-amino-2-(butylamino)-9-[[3-(chloromethyl)phenyl]methyl]-7H-purin-8-one
• CAS: 1421583-19-8
• 化学式: C₁₇H₂₁ClN₆O
• 分子量: 360.846
• InChiKey: ODJPNXPEAWBXGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101.62
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  哌啶 、 6-amino-2-(butylamino)-9-[[3-(chloromethyl)phenyl]methyl]-7H-purin-8-one 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 生成 6-amino-2-butylamino-9-(3-piperidin-1-ylmethylbenzyl)-7,9-dihydropurin-8-one
  参考文献：
  名称：

  Synthesis and evaluation of 8-oxoadenine derivatives as potent Toll-like receptor 7 agonists with high water solubility

  摘要：

  We report the discovery of novel series of highly potent TLR7 agonists based on 8-oxoadenines, 1 and 2 by introducing and optimizing various tertiary amines onto the N(9)-position of the adenine moiety. The introduction of the amino group resulted in not only improved water solubility but also enhanced TLR7 agonistic activity. In particular compound 20 (DSR-6434) indicated an optimal balance between the agonistic potency and high water solubility. It also demonstrated a strong antitumor effect in vivo by intravenous administration in a tumor bearing mice model. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.114
• 作为产物：
  描述：

  在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 6-amino-2-(butylamino)-9-[[3-(chloromethyl)phenyl]methyl]-7H-purin-8-one
  参考文献：
  名称：

  Synthesis and evaluation of 8-oxoadenine derivatives as potent Toll-like receptor 7 agonists with high water solubility

  摘要：

  We report the discovery of novel series of highly potent TLR7 agonists based on 8-oxoadenines, 1 and 2 by introducing and optimizing various tertiary amines onto the N(9)-position of the adenine moiety. The introduction of the amino group resulted in not only improved water solubility but also enhanced TLR7 agonistic activity. In particular compound 20 (DSR-6434) indicated an optimal balance between the agonistic potency and high water solubility. It also demonstrated a strong antitumor effect in vivo by intravenous administration in a tumor bearing mice model. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.114