2-(羧基甲氧基)-5-氟苯甲酸 | 60770-24-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(羧基甲氧基)-5-氟苯甲酸
• 英文名称: 2-(carboxymethoxy)-5-fluorobenzoic acid
• 英文别名: 2-(carboxymethoxy)-5-fluoro-benzoic acid；O-Carboxymethyl-5-fluorsalicylsaeure
• CAS: 60770-24-3
• 化学式: C₉H₇FO₅
• 分子量: 214.15
• InChiKey: VVOKNKUXSAFIDE-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  425.7±30.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-(羧基甲氧基)-5-氟苯甲酸 在 sodium acetate 作用下， 以 四氢呋喃 、 乙酸酐 为溶剂， 反应 5.5h， 生成 2-(5-fluoro-1-benzofuran-3-yl)acetonitrile
  参考文献：
  名称：

  Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties

  摘要：

  A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl) amino]methyl}furan-2-yl)phenol (1, 5-HT6R K-i = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R K-j= 25, 5-HT2AR K-i = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with procognitive properties. (C) 2019 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111857
• 作为产物：
  描述：

  5-氟-2-羟基苯甲酸甲酯 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 2-(羧基甲氧基)-5-氟苯甲酸
  参考文献：
  名称：

  Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties

  摘要：

  A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl) amino]methyl}furan-2-yl)phenol (1, 5-HT6R K-i = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R K-j= 25, 5-HT2AR K-i = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with procognitive properties. (C) 2019 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111857

文献信息

• Novel benzofuran derivatives with dual 5-HT1A receptor and serotonin transporter affinity
  作者：Aranapakam M. Venkatesan、O. Dos Santos、John Ellingboe、Deborah A. Evrard、Boyd L. Harrison、Deborah L. Smith、Rosemary Scerni、Geoffrey A. Hornby、Lee E. Schechter、Terrence H. Andree

  DOI：10.1016/j.bmcl.2009.12.093

  日期：2010.2

  Several benzofuran derivatives linked to a 3-indoletetrahydropyridine through an alkyl chain were prepared and evaluated for serotonin transporter and 5-HT1A receptor affinities. Their design, synthesis and structure–activity relationships are described.

  制备了几种通过烷基链与3-吲哚四氢吡啶连接的苯并呋喃衍生物，并评估了其血清素转运蛋白和5-HT 1A受体的亲和力。描述了它们的设计，合成和结构-活性关系。
• BENZOFURANYL- AND BENZOTHIENYL- PIPERAZINYL QUINOLINES AND METHODS OF THEIR USE
  申请人：Venkatesan Aranapakam Mudumbai

  公开号：US20090054454A1

  公开（公告）日：2009-02-26

  Benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and/or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.

  本专利揭示了苯并呋喃基和苯并噻吩基哌嗪喹啉衍生物以及含有这些化合物的组合物。还揭示了使用苯并呋喃基和苯并噻吩基哌嗪喹啉衍生物以及含有这种组合物在治疗和/或预防与5-羟色胺相关的疾病，如抑郁症和焦虑症的方法。此外，还揭示了制备苯并呋喃基和苯并噻吩基哌嗪喹啉衍生物的方法。
• Piperidinyl indole and tetrohydropyridinyl indole derivatives and method of their use
  申请人：Venkatesan Mudumbai Aranapakam

  公开号：US20050004162A1

  公开（公告）日：2005-01-06

  3-Piperidin-4-yl-1H-indole and 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole derivatives are disclosed. Methods of using the derivatives and compositions containing the derivatives in the prevention and/or treatment of serotonin disorders, such as depression and anxiety, are also disclosed. Additionally, processes for the preparation of 3-piperidin-4-yl-1H-indole and 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole derivatives are disclosed.

  3-哌啶基-1H-吲哚和3-(1,2,3,6-四氢吡啶-4-基)-1H-吲哚衍生物已被披露。还披露了使用这些衍生物以及含有这些衍生物的组合物在预防和/或治疗血清素紊乱，如抑郁症和焦虑症方面的方法。此外，还披露了制备3-哌啶基-1H-吲哚和3-(1,2,3,6-四氢吡啶-4-基)-1H-吲哚衍生物的方法。
• Benzofuranyl-and benzothienyl-piperazinyl quinolines and methods of their use
  申请人：Venkatesan Mudumbai Aranapakam

  公开号：US20050059673A1

  公开（公告）日：2005-03-17

  Benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and/or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.

  本发明涉及苯并呋喃基-和苯并噻吩基-哌嗪基喹啉衍生物及含有该类化合物的组合物。本发明还涉及使用苯并呋喃基-和苯并噻吩基-哌嗪基喹啉衍生物及含有该类组合物治疗和/或预防与血清素相关的疾病，例如抑郁和焦虑。此外，还公开了制备苯并呋喃基-和苯并噻吩基-哌嗪基喹啉衍生物的方法。
• PIPERIDINYL INDOLE AND TETROHYDROPYRIDINYL INDOLE DERIVATIVES AND METHODS OF THEIR USE
  申请人：Venkatesan Mudumbai Aranapakam

  公开号：US20070225319A1

  公开（公告）日：2007-09-27

  3-Piperidin-4-yl-1H-indole and 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole derivatives are disclosed. Methods of using the derivatives and compositions containing the derivatives in the prevention and/or treatment of serotonin disorders, such as depression and anxiety, are also disclosed. Additionally, processes for the preparation of 3-piperidin-4-yl-1H-indole and 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole derivatives are disclosed.

  本发明揭示了3-哌啶基-1H-吲哚和3-(1,2,3,6-四氢-吡啶-4-基)-1H-吲哚衍生物。本发明还揭示了使用这些衍生物和含有这些衍生物的组合物在预防和/或治疗血清素紊乱，如抑郁症和焦虑症方面的方法。此外，本发明还揭示了制备3-哌啶基-1H-吲哚和3-(1,2,3,6-四氢-吡啶-4-基)-1H-吲哚衍生物的过程。