9-氯菲-3-羧酸 | 7473-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 9-氯菲-3-羧酸
• 英文名称: 9-chlorophenanthrene-3-carboxylic acid
• 英文别名: 9-Chlor-phenanthren-3-carbonsaeure；3-Phenanthrenecarboxylicacid, 9-chloro-
• CAS: 7473-69-0
• 化学式: C₁₅H₉ClO₂
• 分子量: 256.688
• InChiKey: JAIIDCPBHNDDLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-氯菲-3-羧酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 9-Chlorophenanthrene-3-carbonyl chloride
  参考文献：
  名称：

  Piperazine-2,3-dicarboxylic Acid Derivatives as Dual Antagonists of NMDA and GluK1-Containing Kainate Receptors

  摘要：

  Competitive N-methyl-D-aspartate receptor (NMDAR) antagonists bind to the GluN2 subunit, of which there are four types (GluN2A-D). We report that some N-1-substituted derivatives of cis-piperazine-2,3-dicarboxylic acid display improved relative affinity for GluN2C and GluN2D versus GluN2A and GluN2B. These derivatives also display subtype selectivity among the more distantly related kainate receptor family. Compounds 18i and (-)-4 were the most potent kainate receptor antagonists, and 18i was selective for GluK1 versus GluK2, GluK3 and AMPA receptors. Modeling studies revealed structural features required for activity at GluK1 subunits and suggested that S674 was vital for antagonist activity. Consistent with this hypothesis, replacing the equivalent residue in GluK3 (alanine) with a serine imparts 18i antagonist activity. Antagonists with dual GluN2D and GluK1 antagonist activity may have beneficial effects in various neurological disorders. Consistent with this idea, antagonist 18i (30 mg/kg ip) showed antinociceptive effects in an animal model of mild nerve injury.

  DOI：

  10.1021/jm201230z
• 作为产物：
  描述：

  3-Acetyl-9-chlorophenanthrene 在 溴 、 sodium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以77%的产率得到9-氯菲-3-羧酸
  参考文献：
  名称：

  Piperazine-2,3-dicarboxylic Acid Derivatives as Dual Antagonists of NMDA and GluK1-Containing Kainate Receptors

  摘要：

  Competitive N-methyl-D-aspartate receptor (NMDAR) antagonists bind to the GluN2 subunit, of which there are four types (GluN2A-D). We report that some N-1-substituted derivatives of cis-piperazine-2,3-dicarboxylic acid display improved relative affinity for GluN2C and GluN2D versus GluN2A and GluN2B. These derivatives also display subtype selectivity among the more distantly related kainate receptor family. Compounds 18i and (-)-4 were the most potent kainate receptor antagonists, and 18i was selective for GluK1 versus GluK2, GluK3 and AMPA receptors. Modeling studies revealed structural features required for activity at GluK1 subunits and suggested that S674 was vital for antagonist activity. Consistent with this hypothesis, replacing the equivalent residue in GluK3 (alanine) with a serine imparts 18i antagonist activity. Antagonists with dual GluN2D and GluK1 antagonist activity may have beneficial effects in various neurological disorders. Consistent with this idea, antagonist 18i (30 mg/kg ip) showed antinociceptive effects in an animal model of mild nerve injury.

  DOI：

  10.1021/jm201230z

文献信息

• ATTEMPTS TO FIND NEW ANTIMALARIALS. XII. DERIVATIVES OF PHENANTHRENE, IV. 1 (OR 8)-ACETYL-9-HALOPHENANTHRENE
  作者：J. SCHULTZ、M. A. GOLDBERG、E. P. ORDAS、G. CARSCH

  DOI：10.1021/jo01174a004

  日期：1946.7
• [EN] POSITIVE AND NEGATIVE MODULATORS OF NMDA RECEPTORS<br/>[FR] MODULATEURS POSITIFS ET NÉGATIFS DES RÉCEPTEURS NMDA
  申请人：UNIV NEBRASKA

  公开号：WO2012019106A2

  公开（公告）日：2012-02-09

  Disclosed herein are compounds useful as modulators of an NMDA receptor. Further disclosed are methods of modulating an NMDA receptor using these compounds, and methods of treating various NMDA-receptor disorders, such as, for example, schizophrenia, post-traumatic stress disorder, Alzheimer's disease, and pain.
• Piperazine-2,3-dicarboxylic Acid Derivatives as Dual Antagonists of NMDA and GluK1-Containing Kainate Receptors
  作者：Mark W. Irvine、Blaise M. Costa、Daniel Dlaboga、Georgia R. Culley、Richard Hulse、Caroline L. Scholefield、Palmi Atlason、Guangyu Fang、Richard Eaves、Richard Morley、Maria B. Mayo-Martin、Mascia Amici、Zuner A. Bortolotto、Lucy Donaldson、Graham L. Collingridge、Elek Molnár、Daniel T. Monaghan、David E. Jane

  DOI：10.1021/jm201230z

  日期：2012.1.12

  Competitive N-methyl-D-aspartate receptor (NMDAR) antagonists bind to the GluN2 subunit, of which there are four types (GluN2A-D). We report that some N-1-substituted derivatives of cis-piperazine-2,3-dicarboxylic acid display improved relative affinity for GluN2C and GluN2D versus GluN2A and GluN2B. These derivatives also display subtype selectivity among the more distantly related kainate receptor family. Compounds 18i and (-)-4 were the most potent kainate receptor antagonists, and 18i was selective for GluK1 versus GluK2, GluK3 and AMPA receptors. Modeling studies revealed structural features required for activity at GluK1 subunits and suggested that S674 was vital for antagonist activity. Consistent with this hypothesis, replacing the equivalent residue in GluK3 (alanine) with a serine imparts 18i antagonist activity. Antagonists with dual GluN2D and GluK1 antagonist activity may have beneficial effects in various neurological disorders. Consistent with this idea, antagonist 18i (30 mg/kg ip) showed antinociceptive effects in an animal model of mild nerve injury.