4-(4-(4-chlorophenoxy)butoxy)benzaldehyde | 1226405-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-(4-chlorophenoxy)butoxy)benzaldehyde
• 英文别名: 4-[4-(4-chlorophenoxy)butoxy]benzaldehyde
• CAS: 1226405-13-5
• 化学式: C₁₇H₁₇ClO₃
• 分子量: 304.773
• InChiKey: KHDOUMZKOAZMHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4-(4-chlorophenoxy)butoxy)benzaldehyde 在 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 182.0h， 生成 (E)-4-(carboxymethoxy)-3-(3-(4-(4-(4-chlorophenoxy)butoxy)phenyl)acryloyl)benzoic acid
  参考文献：
  名称：

  Structure-based drug design using GPCR homology modeling: Toward the discovery of novel selective CysLT2 antagonists

  摘要：

  3D structure of CysLT2 receptor was constructed by using homology modeling and molecular simulations. The binding pocket of CysLT2 receptor and the proposition of the interaction mode between CysLT2 and HAMI3379 were identified. A series of dicarboxylated chalcones was then virtually evaluated through molecular docking studies. A total of six compounds 13a-f with preferable scores was further synthesized and tested for CysLT2 antagonistic activities by determination of the cytosolic free Ca2+ levels in HEK293 cells. Compounds 13e and 13f exhibited potent and selective CysLT2 antagonistic activities with IC50 values being 7.5 and 0.25 mu M, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.041
• 作为产物：
  描述：

  1-(4-溴丁氧基)-4-氯苯 、 对羟基苯甲醛 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以77%的产率得到4-(4-(4-chlorophenoxy)butoxy)benzaldehyde
  参考文献：
  名称：

  羧基化查尔酮衍生物作为CysLT 1拮抗剂的药理学鉴定，合成和生物学评估

  摘要：

  使用Catalyst / HypoGen程序开发了对CysLT 1拮抗剂具有良好预测能力的药效团模型（Hypo1）。使用Hypo1对由羧化查耳酮组成的内部数据库进行了虚拟筛选。合成了命中的命中26a，26b，27a和27b，并对其进行了生物学评估，其结果表明这些化合物显示出中等至良好的CysLT 1拮抗活性。这项研究表明，生成的模型（Hypo1）是用于新型CysLT 1拮抗剂的前导优化的可靠且有用的工具。

  DOI：

  10.1016/j.bmc.2010.06.047

文献信息

• Pharmacophore identification, synthesis, and biological evaluation of carboxylated chalcone derivatives as CysLT1 antagonists
  作者：Xiaowu Dong、Li Wang、Xueqin Huang、Tao Liu、Erqing Wei、Lilin Du、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.bmc.2010.06.047

  日期：2010.8

  pharmacophore model (Hypo1) with a well prediction capacity for CysLT1 antagonists was developed using Catalyst/HypoGen program. Virtual screening against an in-house database consisted of carboxylated chalcones using Hypo1 was performed. Retrieved hits 26a, 26b, 27a, and 27b were synthesized and biological evaluated, the results of which demonstrated that these compounds showed moderate to good CysLT1 antagonistic

  使用Catalyst / HypoGen程序开发了对CysLT 1拮抗剂具有良好预测能力的药效团模型（Hypo1）。使用Hypo1对由羧化查耳酮组成的内部数据库进行了虚拟筛选。合成了命中的命中26a，26b，27a和27b，并对其进行了生物学评估，其结果表明这些化合物显示出中等至良好的CysLT 1拮抗活性。这项研究表明，生成的模型（Hypo1）是用于新型CysLT 1拮抗剂的前导优化的可靠且有用的工具。
• Structure-based drug design using GPCR homology modeling: Toward the discovery of novel selective CysLT2 antagonists
  作者：Xiaowu Dong、Yanmei Zhao、Xueqin Huang、Kana Lin、Jianzhong Chen、Erqing Wei、Tao Liu、Yongzhou Hu

  DOI：10.1016/j.ejmech.2013.01.041

  日期：2013.4

  3D structure of CysLT2 receptor was constructed by using homology modeling and molecular simulations. The binding pocket of CysLT2 receptor and the proposition of the interaction mode between CysLT2 and HAMI3379 were identified. A series of dicarboxylated chalcones was then virtually evaluated through molecular docking studies. A total of six compounds 13a-f with preferable scores was further synthesized and tested for CysLT2 antagonistic activities by determination of the cytosolic free Ca2+ levels in HEK293 cells. Compounds 13e and 13f exhibited potent and selective CysLT2 antagonistic activities with IC50 values being 7.5 and 0.25 mu M, respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.