[4-[[6-Amino-8-bromo-2-(butylamino)purin-9-yl]methyl]phenyl]methanol | 1421583-11-0

• 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: [4-[[6-Amino-8-bromo-2-(butylamino)purin-9-yl]methyl]phenyl]methanol
• 英文别名: [4-[[6-amino-8-bromo-2-(butylamino)purin-9-yl]methyl]phenyl]methanol
• CAS: 1421583-11-0
• 化学式: C₁₇H₂₁BrN₆O
• 分子量: 405.297
• InChiKey: URNDAWKBJMDZQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-[[6-Amino-8-bromo-2-(butylamino)purin-9-yl]methyl]phenyl]methanol 在 盐酸 、 氯化亚砜 、 水 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 6-amino-2-butylamino-9-(4-morpholin-4-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：

  4-(氯甲基)苯甲基醇 在 溴 、 sodium acetate 、 potassium carbonate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 [4-[[6-Amino-8-bromo-2-(butylamino)purin-9-yl]methyl]phenyl]methanol
  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

文献信息

• COMBINATION THERAPY COMPOSITIONS AND METHODS FOR TREATING CANCERS
  申请人：BIRDIE BIOPHARMACEUTICALS, INC.

  公开号：US20170056391A1

  公开（公告）日：2017-03-02

  The present invention relates to therapeutic combinations and methods for treating cancers using combination therapy.
• ANTI-PD-L1 COMBINATIONS FOR TREATING TUMORS
  申请人：BIRDIE BIOPHARMACEUTICALS, INC.

  公开号：US20170114137A1

  公开（公告）日：2017-04-27

  The present invention relates to therapeutic combinations and methods for treating cancers using combination therapy.
• Anti PD-L1 Conjugates for Treating Tumors
  申请人：BIRDIE BIOPHARMACEUTICALS, INC.

  公开号：US20170290923A1

  公开（公告）日：2017-10-12

  The present invention discloses anti-PD-L/PD-1 Axis antibody conjugates for targeted immunotherapy, as well as compositions comprising said conjugates. Further, the present invention discloses the use of the conjugates in the treatment of tumor/cancer.
• Synthesis and evaluation of 8-oxoadenine derivatives as potent Toll-like receptor 7 agonists with high water solubility
  作者：Tomoaki Nakamura、Hiroki Wada、Hirotaka Kurebayashi、Tom McInally、Roger Bonnert、Yoshiaki Isobe

  DOI：10.1016/j.bmcl.2012.11.114

  日期：2013.2

  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.