4-(3-(piperidin-1-yl)propoxy)-2-hydroxybenzoic acid | 761455-28-1

• 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: 4-(3-(piperidin-1-yl)propoxy)-2-hydroxybenzoic acid
• 英文别名: 2-Hydroxy-4-(3-piperidin-1-ylpropoxy)benzoic acid
• CAS: 761455-28-1
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: LBAIUPMLBWLPIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-(piperidin-1-yl)propoxy)-2-hydroxybenzoic acid 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-(3-(piperidin-1-yl)propoxy)-N-(3-(trifluoromethyl)phenyl)-2-hydroxybenzamide
  参考文献：
  名称：

  Synthesis and Evaluation of Salicylanilide Derivatives as Potential Epidermal Growth Factor Receptor Inhibitors

  摘要：

  Two series of novel salicylanilide were synthesized as potential epidermal growth factor receptor (EGFR) inhibitors. The enzyme inhibitory activity against EGFR of all compounds was carried out, and their antiproliferative activities against the A549 and A431 cell lines were also evaluated. Of the compounds studied, majority of them exhibited high antiproliferative activities compared with gefitinib; especially, 12a and 12b exhibited stronger inhibitory activity against EGFR with IC50 values of 10.4 ± 2.25 and 15.4 ± 2.33 nm, respectively, which were comparable to the positive control of gefitinib (IC50 = 12.1 ± 2.21 nm). Compound 12b also showed outstanding inhibitory activity against A431 and A549 cell lines with the IC50 values of 0.42 ± 0.43 μm and 0.57 ± 0.43 μm, which was better than the positive controls. In the molecular modeling study, compound 12b was bound into the active pocket of EGFR with two hydrogen bond and with minimum binding free energy ▵Gb = −25.1125 kcal/mol. The result also suggested that compound 12b could bind the EGFR kinase well.

  DOI：

  10.1111/cbdd.12383
• 作为产物：
  描述：

  4-(3-bromo-propoxy)-2-hydroxybenzoic acid methyl ester 在 碳酸氢钠 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 反应 12.0h， 生成 4-(3-(piperidin-1-yl)propoxy)-2-hydroxybenzoic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Salicylanilide Derivatives as Potential Epidermal Growth Factor Receptor Inhibitors

  摘要：

  Two series of novel salicylanilide were synthesized as potential epidermal growth factor receptor (EGFR) inhibitors. The enzyme inhibitory activity against EGFR of all compounds was carried out, and their antiproliferative activities against the A549 and A431 cell lines were also evaluated. Of the compounds studied, majority of them exhibited high antiproliferative activities compared with gefitinib; especially, 12a and 12b exhibited stronger inhibitory activity against EGFR with IC50 values of 10.4 ± 2.25 and 15.4 ± 2.33 nm, respectively, which were comparable to the positive control of gefitinib (IC50 = 12.1 ± 2.21 nm). Compound 12b also showed outstanding inhibitory activity against A431 and A549 cell lines with the IC50 values of 0.42 ± 0.43 μm and 0.57 ± 0.43 μm, which was better than the positive controls. In the molecular modeling study, compound 12b was bound into the active pocket of EGFR with two hydrogen bond and with minimum binding free energy ▵Gb = −25.1125 kcal/mol. The result also suggested that compound 12b could bind the EGFR kinase well.

  DOI：

  10.1111/cbdd.12383

文献信息

• Kcnq channel modulating compounds and their pharmaceutical use
  申请人：Brown Dalby William

  公开号：US20060173058A1

  公开（公告）日：2006-08-03

  This invention relates to novel compounds useful as modulators of the KCNQ channel, to pharmaceutical compositions comprising these compounds, and to methods of treatment herewith.

  本发明涉及一种作为KCNQ通道调节剂有用的新化合物，涉及包含这些化合物的制药组合物，以及使用这些化合物进行治疗的方法。
• KCNQ CHANNEL MODULATING COMPOUNDS AND THEIR PHARMACEUTICAL USE
  申请人：NEUROSEARCH A/S

  公开号：EP1603858A2

  公开（公告）日：2005-12-14
• US7741352B2
  申请人：——

  公开号：US7741352B2

  公开（公告）日：2010-06-22
• [EN] NOVEL KCNQ CHANNEL MODULATING COMPOUNDS AND THEIR USE<br/>[FR] NOUVEAUX COMPOSES MODULANT LE CANAL KCNQ ET LEUR UTILISATION
  申请人：NEUROSEARCH AS

  公开号：WO2004080377A2

  公开（公告）日：2004-09-23

  This invention relates to compounds of the general formula (I) useful as modulators of the KCNQ channel, to pharmaceutical compositions comprising these compounds, and to methods of treatment herewith.