4-(2-methylphenoxy)benzoic acid | 355154-50-6

• 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-(2-methylphenoxy)benzoic acid
• 英文别名: 4-carboxyphenoxyphenyl methane
• CAS: 355154-50-6
• 化学式: C₁₄H₁₂O₃
• mdl: MFCD02068125
• 分子量: 228.247
• InChiKey: NDATUJNTHWUURZ-UHFFFAOYSA-N

物化性质

• 沸点：
  368.9±25.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-methylphenoxy)benzoic acid 在 氯化亚砜 作用下， 生成 4-chlorocarbonylphenoxy phenyl methane
  参考文献：
  名称：

  Phenyl alkyleneoxy phenyl alkanoic acid esters

  摘要：

  具有降血脂和/或降血糖活性的药物组合物，包含一种取代的（4-羧基苯氧基）苯基烷衍生物。

  公开号：

  US03983164A1
• 作为产物：
  描述：

  邻甲酚 在 sodium chlorite 、 potassium dihydrogenphosphate 、 2-甲基-2-丁烯 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 4-(2-methylphenoxy)benzoic acid
  参考文献：
  名称：

  Discovery of CS-2100, a potent, orally active and S1P3-sparing S1P1 agonist

  摘要：

  S1P(3)-sparing S1P(1) agonists have attracted attention as a suppressant of autoimmunity with reduced side effects. Our synthetic efforts and extensive SAR studies led to the discovery of 10b named CS-2100 with the EC50 value of 4.0 nM for human S1P(1) and over 5000-fold selectivity against S1P(3). The in vivo immunosuppressive efficacy was evaluated in rats on host versus graft reaction and the ID50 value was determined at 0.407 mg/kg. The docking studies of CS-2100 with the homology model of S1P(1) and S1P(3) showed that the ethyl group on the thiophene ring of CS-2100 was sterically hindered by Phe263 in S1P(3), not in the case of Leu276 in S1P(1). This observation gives an explanation for the excellent S1P(3)-sparing characteristic of CS-2100. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.019

文献信息

• NOVEL COMPOUNDS
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20150057298A1

  公开（公告）日：2015-02-26

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R 1 , X, m, R 2 , Y, R 3 , Z, n, R 4 , A and B are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了化合物的公式（I）及其药用盐，其中R1、X、m、R2、Y、R3、Z、n、R4、A和B的定义如规范中所述，以及它们的制备方法、含有它们的药物组合物以及它们在治疗中的应用。
• AMIDE DERIVATIVES AS LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20160207880A1

  公开（公告）日：2016-07-21

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R 1 , X, m, R 2 , Y, R 3 , Z, n, R 4 , A and B are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了公式（I）的化合物及其药学上可接受的盐，其中R1、X、m、R2、Y、R3、Z、n、R4、A和B如规范中定义，以及其制备过程、包含它们的制药组合物和它们在治疗中的应用。
• Amide derivatives as lysophosphatidic acid receptor antagonists
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US10100018B2

  公开（公告）日：2018-10-16

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1, X, m, R2, Y, R3, Z, n, R4, A and B are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了式 (I) 化合物及其药学上可接受的盐类、 其中 R1、X、m、R2、Y、R3、Z、n、R4、A 和 B 如说明书中所定义，本发明还提供了制备它们的工艺、含有它们的药物组合物以及它们在治疗中的用途。
• Addressing cytotoxicity of 1,4-biphenyl amide derivatives: Discovery of new potent and selective 17β-hydroxysteroid dehydrogenase type 2 inhibitors
  作者：Emanuele Marco Gargano、Enrico Perspicace、Angelo Carotti、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1016/j.bmcl.2015.11.047

  日期：2016.1

  Four different classes of new 17 beta-hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) inhibitors were synthesized, in order to lower the cytotoxicity exhibited by the lead compound A, via disrupting the linearity and the aromaticity of the biphenyl moiety. Compounds 3, 4, 7a and 8 displayed comparable or better inhibitory activity and selectivity, as well as a lower cytotoxic effect, compared to the reference compound A. The best compound 4 (IC50 = 160 nM, selectivity factor = 168, LD50 approximate to 25 mu M) turned out as new lead compound for inhibition of 17 beta-HSD2. (C) 2015 Elsevier Ltd. All rights reserved.
• Discovery and Characterization of MAPK-activated Protein Kinase-2 Prevention of Activation Inhibitors
  作者：John G. Cumming、Judit É. Debreczeni、Fredrik Edfeldt、Emma Evertsson、Martin Harrison、Geoffrey A. Holdgate、Michael J. James、Scott G. Lamont、Keith Oldham、Jane E. Sullivan、Stuart L. Wells

  DOI：10.1021/jm501038s

  日期：2015.1.8

  Two structurally distinct series of novel, MAPK-activated kinase-2 prevention of activation inhibitors have been discovered by high throughput screening. Preliminary structureactivity relationship (SAR) studies revealed substructural features that influence the selective inhibition of the activation by p38 alpha of the downstream kinase MK2 in preference to an alternative substrate, MSK1. Enzyme kinetics, surface plasmon resonance (SPR), 2D protein NMR, and X-ray crystallography were used to determine the binding mode and the molecular mechanism of action. The compounds bind competitively to the ATP binding site of p38 alpha but unexpectedly with higher affinity in the p38 alpha-MK2 complex compared with p38 alpha alone. This observation is hypothesized to be the origin of the substrate selectivity. The two lead series identified are suitable for further investigation for their potential to treat chronic inflammatory diseases with improved tolerability over previously studied p38 alpha inhibitors.