1,1'-(1,4-phenylene)bis{3-[1-(adamantan-1-yl)ethyl]urea} | 1607795-41-4

• 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: 1,1'-(1,4-phenylene)bis{3-[1-(adamantan-1-yl)ethyl]urea}
• 英文别名: 1,4-(phenylene)bis{[(adamant-1-yl)ethyl-1]urea}；1-[1-(1-Adamantyl)ethyl]-3-[4-[1-(1-adamantyl)ethylcarbamoylamino]phenyl]urea；1-[1-(1-adamantyl)ethyl]-3-[4-[1-(1-adamantyl)ethylcarbamoylamino]phenyl]urea
• CAS: 1607795-41-4
• 化学式: C₃₂H₄₆N₄O₂
• 分子量: 518.743
• InChiKey: GOWVOMZIZCQSCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  82.3
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  盐酸金刚乙胺 、 对苯二异氰酸酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以98%的产率得到1,1'-(1,4-phenylene)bis{3-[1-(adamantan-1-yl)ethyl]urea}
  参考文献：
  名称：

  含二金刚烷基的对称双脲作为人可溶性环氧化物水解酶的靶向抑制剂的合成和性质

  摘要：

  已经合成了一系列以靶标为导向的人可溶性环氧化物水解酶的竞争性抑制剂。这些化合物在低至 4 nM 的浓度下仍保持抑制特性。基于分子建模的结果，表明该系列化合物的高抑制活性是通过与酶活性位点结合的独特模式实现的。

  DOI：

  10.1134/s1068162016030067

文献信息

• Synthesis of adamantyl-containing 1,3-disubstituted diureas and thioureas, efficient targeted inhibitors of human soluble epoxide hydrolase
  作者：G. M. Butov、V. V. Burmistrov、D. V. Danilov、D. A. Pitushkin、C. Morisseau、B. D. Hammock

  DOI：10.1007/s11172-015-1043-y

  日期：2015.7

  A series of adamantyl-containing 1,3-disubstituted diureas and thioureas containing different spacers between the ureylene group and the adamantyl substituent has been synthesized, their inhibitory activity against mammalian and human soluble epoxide hydrolase (sEH, E.C. 3.3.2.10) has been examined. The compounds synthesized were found to exhibit high inhibitory activity on the 0.4–2.8 nmol L−1 level. The dependence between the inhibitor structure and its activity was established

  合成了一系列含有刚性烷基的1,3-二取代二脲和硫脲，这些化合物在脲基团与刚性烷基取代基之间具有不同的间隔，且已研究其对哺乳动物和人类可溶性环氧化酶水解酶（sEH，E.C. 3.3.2.10）的抑制活性。合成的化合物在0.4–2.8 nmol L−1的浓度范围内表现出高抑制活性。抑制剂结构与其活性之间的关系已经确定。
• Symmetric adamantyl-diureas as soluble epoxide hydrolase inhibitors
  作者：Vladimir Burmistrov、Christophe Morisseau、Kin Sing Stephen Lee、Diyala S. Shihadih、Todd R. Harris、Gennady M. Butov、Bruce D. Hammock

  DOI：10.1016/j.bmcl.2014.03.016

  日期：2014.5

  A series of inhibitors of the soluble epoxide hydrolase (sEH) containing two urea groups has been developed. Inhibition potency of the described compounds ranges from 2.0 mu M to 0.4 nM. 1,6-(Hexamethylene)bis[(adamant-1-yl) urea] (3b) was found to be a potent slow tight binding inhibitor (IC50 = 0.5 nM) with a strong binding to sEH (K-i = 3.1 nM) and a moderately long residence time on the enzyme (k(off) = 1.05 x 10(-3) s(-1); t(1/2) = 11 min). (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and properties of diadamantyl-containing symmetric diureas as target-oriented inhibitors of human soluble epoxide hydrolase
  作者：V. V. Burmistrov、G. M. Butov、D. S. Karlov、V. A. Palyulin、N. S. Zefirov、C. Morisseau、B. D. Hammock

  DOI：10.1134/s1068162016030067

  日期：2016.7

  A series of target-oriented competitive inhibitors of human soluble epoxide hydrolase have been synthesized. The compounds retain the inhibitory properties at concentrations down to 4 nM. Based on the results of molecular modeling, it has been shown that the high inhibitory activity of this series of compounds is achieved by a unique mode of the binding to the active site of the enzyme.

  已经合成了一系列以靶标为导向的人可溶性环氧化物水解酶的竞争性抑制剂。这些化合物在低至 4 nM 的浓度下仍保持抑制特性。基于分子建模的结果，表明该系列化合物的高抑制活性是通过与酶活性位点结合的独特模式实现的。