2-(2-hydroxyethyl)-4-methoxybenzoic acid | 947150-37-0

• 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: 2-(2-hydroxyethyl)-4-methoxybenzoic acid
• CAS: 947150-37-0
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: FBRJKTJCHDJUEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethyl)-4-methoxybenzoic acid 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以30%的产率得到3-hydroxy-6-methoxy-3,4-dihydroisobenzopyran-1-one
  参考文献：
  名称：

  Illudalic acid as a potential LAR inhibitor: Synthesis, SAR, and preliminary studies on the mechanism of action

  摘要：

  A novel synthesis of the human leukocyte common antigen-related (LAR) phosphatase inhibitor, illudalic acid, has been achieved by a route more amenable to structure modi. cations. A series of simpler analogues of illudalic acid was synthesized and evaluated for potency in inhibiting LAR. The structure -activity relationship (SAR) study has shown that the 5-formyl group and the hemi-acetal lactone are crucial for effective inhibition of LAR activity, and are the key pharmacophores of illudalic acid. The fused dimethylcyclopentene ring moiety evidently helps to enhance the potency of illudalic acid against LAR. A preliminary study of the mechanism of action of illudalic acid against LAR was conducted using electrospray ionization mass spectrometry (ESI-MS) and molecular docking techniques. The results are in full agreement with the described mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.014
• 作为产物：
  描述：

  methyl 2-(2-hydroxyethyl)-4-methoxybenzoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以96%的产率得到2-(2-hydroxyethyl)-4-methoxybenzoic acid
  参考文献：
  名称：

  Illudalic acid as a potential LAR inhibitor: Synthesis, SAR, and preliminary studies on the mechanism of action

  摘要：

  A novel synthesis of the human leukocyte common antigen-related (LAR) phosphatase inhibitor, illudalic acid, has been achieved by a route more amenable to structure modi. cations. A series of simpler analogues of illudalic acid was synthesized and evaluated for potency in inhibiting LAR. The structure -activity relationship (SAR) study has shown that the 5-formyl group and the hemi-acetal lactone are crucial for effective inhibition of LAR activity, and are the key pharmacophores of illudalic acid. The fused dimethylcyclopentene ring moiety evidently helps to enhance the potency of illudalic acid against LAR. A preliminary study of the mechanism of action of illudalic acid against LAR was conducted using electrospray ionization mass spectrometry (ESI-MS) and molecular docking techniques. The results are in full agreement with the described mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.014

文献信息

• NOVEL AZACYCLYL-SUBSTITUTED ARYLDIHYDROISOQUINOLINONES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MEDICAMENTS
  申请人：SCHWINK Lothar

  公开号：US20090264403A1

  公开（公告）日：2009-10-22

  The invention relates to azacyclyl-substituted aryldihydroisoquinolinones and their derivatives, and their physiologically tolerated salts and physiologically functional derivatives, their preparation, medicaments comprising at least one azacyclyl-substituted aryldihydroisoquinolinone of the invention or its derivative, and the use of the azacyclyl-substituted aryidihydroisoquinolinones of the invention and their derivatives as MCH antagonists.

  本发明涉及含氮杂环取代的芳基二氢异喹啉酮及其衍生物、其生理上可耐受的盐和生理功能衍生物、其制备方法、包含本发明中至少一种含氮杂环取代的芳基二氢异喹啉酮或其衍生物的药物以及将本发明中的含氮杂环取代的芳基二氢异喹啉酮及其衍生物用作MCH拮抗剂。
• AZACYCLYL-SUBSTITUTED ARYLDIHYDROISOQUINOLINONES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MEDICAMENTS
  申请人：SANOFI

  公开号：EP1987020B1

  公开（公告）日：2012-10-03
• US8822495B2
  申请人：——

  公开号：US8822495B2

  公开（公告）日：2014-09-02
• [EN] AZACYCLYL-SUBSTITUTED ARYLDIHYDROISOQUINOLINONES, PROCESS FOR THEIR PREPARATION AND THEIR USE AS MEDICAMENTS<br/>[FR] NOUVELLES ARYLDIHYDROISOQUINOLINONES À SUBSTITUTION AZACYCLYLE, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR UTILISATION COMME MÉDICAMENTS
  申请人：SANOFI AVENTIS

  公开号：WO2007093364A1

  公开（公告）日：2007-08-23

  [EN] The invention relates to azacyclyl-substituted aryldihydroisoquinolinones and their derivatives, and their physiologically tolerated salts and physiologically functional derivatives, their preparation, medicaments comprising at least one azacyclyl-substituted aryldihydroisoquinolinone of the invention or its derivative, and the use of the azacyclyl-substituted aryldihydroisoquinolinones of the invention and their derivatives as MCH antagonists.
  [FR] L'invention concerne des aryldihydroisoquinolinones à substitution azacyclyle et leurs dérivés ainsi que leurs sels physiologiquement tolérés et leurs dérivés physiologiquement fonctionnels, leur préparation, des médicaments comprenant au moins une aryldihydroisoquinolinone à substitution azacyclyle de l'invention ou un de ses dérivés, ainsi que l'utilisation des aryldihydroisoquinolinones à substitution azacyclyle de l'invention et de leurs dérivés comme antagonistes de l'hormone de mélanoconcentration (MCH).