8-(6-bromo-3,4-methylenedioxyphenylthio)-9-(hex-5-ynyl)adenine | 1243536-40-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 8-(6-bromo-3,4-methylenedioxyphenylthio)-9-(hex-5-ynyl)adenine
• 英文别名: 8-(6-bromobenzo[d][1,3]dioxol-5-ylthio)-9-(hex-5-ynyl)-9H-purin-6-amine；8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-hex-5-ynylpurin-6-amine
• CAS: 1243536-40-4
• 化学式: C₁₈H₁₆BrN₅O₂S
• 分子量: 446.327
• InChiKey: PHFSKRFRIKVHQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(6-bromo-3,4-methylenedioxyphenylthio)-9-(hex-5-ynyl)adenine 、 3,6,9,12,15-五氧杂十七烷-1,17-二基二-叠氮化物 在 铜 、 copper(II) sulfate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到9-[4-[1-[2-[2-[2-[2-[2-[2-[4-[4-[6-Amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]purin-9-yl]butyl]triazol-1-yl]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]triazol-4-yl]butyl]-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]purin-6-amine
  参考文献：
  名称：

  Efficient synthesis of Hsp90 inhibitor dimers as potential antitumor agents

  摘要：

  The PU-H58-dimers 13a-15b were efficiently synthesized and their biological properties were evaluated. The copper-catalyzed alkyne azide coupling was effective in simultaneously linking three components via a triazole formation to afford the target dimers. These synthesized dimers exhibited binding affinity to the N-terminal domain of Hsp90, cytotoxicity, and client degradation activity although these activities were comparative or weak comparable with that of the parent compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.075
• 作为产物：
  描述：

  8-(7-bromo-2,3-dihydro-benzo[1,4]dioxin-6-ylsulfanyl)adenine 、 5-己炔-1-醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以67%的产率得到8-(6-bromo-3,4-methylenedioxyphenylthio)-9-(hex-5-ynyl)adenine
  参考文献：
  名称：

  Efficient synthesis of Hsp90 inhibitor dimers as potential antitumor agents

  摘要：

  The PU-H58-dimers 13a-15b were efficiently synthesized and their biological properties were evaluated. The copper-catalyzed alkyne azide coupling was effective in simultaneously linking three components via a triazole formation to afford the target dimers. These synthesized dimers exhibited binding affinity to the N-terminal domain of Hsp90, cytotoxicity, and client degradation activity although these activities were comparative or weak comparable with that of the parent compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.075

文献信息

• Efficient synthesis of Hsp90 inhibitor dimers as potential antitumor agents
  作者：Hironori Sekiguchi、Kazuhiro Muranaka、Akiko Osada、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1016/j.bmc.2010.05.075

  日期：2010.8

  The PU-H58-dimers 13a-15b were efficiently synthesized and their biological properties were evaluated. The copper-catalyzed alkyne azide coupling was effective in simultaneously linking three components via a triazole formation to afford the target dimers. These synthesized dimers exhibited binding affinity to the N-terminal domain of Hsp90, cytotoxicity, and client degradation activity although these activities were comparative or weak comparable with that of the parent compound. (C) 2010 Elsevier Ltd. All rights reserved.