9-(4-methylpent-1-yl)phenanthrene-3-carboxylic acid | 1333213-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9-(4-methylpent-1-yl)phenanthrene-3-carboxylic acid
• 英文别名: UBP 646；9-(4-Methylpentyl)phenanthrene-3-carboxylic acid；9-(4-methylpentyl)phenanthrene-3-carboxylic acid
• CAS: 1333213-35-6
• 化学式: C₂₁H₂₂O₂
• 分子量: 306.404
• InChiKey: RVXZSOOCKAKOHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 9-(4-methylpent-1-en-1-yl)phenanthrene-3-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 为溶剂， 20.0~75.0 ℃ 、300.01 kPa 条件下， 反应 18.0h， 生成 9-(4-methylpent-1-yl)phenanthrene-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of a Series of Novel 3,9-Disubstituted Phenanthrenes as Analogues of Known N-Methyl-d-aspartate Receptor Allosteric Modulators

  摘要：

  9-取代菲3-羧酸据报道具有对N-甲基-d-天冬氨酸（NMDA）受体的变构调节活性。该受体被兴奋性神经递质l-谷氨酸激活，并已被认为与一系列神经系统疾病（如精神分裂症、癫痫和慢性疼痛）以及神经退行性疾病（如阿尔茨海默病）有关。本文描述了从几种常见中间体出发合成一系列新型3,9-二取代菲衍生物的便捷方法。这些新的菲衍生物将有助于阐明对NMDA受体的变构调节的结构要求。

  DOI：

  10.1055/s-0034-1380114

文献信息

• [EN] COMPOUNDS FOR USE IN MODULATING THE NMDA RECEPTOR<br/>[FR] MODULATEURS POSITIFS ET NÉGATIFS DES RÉCEPTEURS NMDA
  申请人：UNIV NEBRASKA

  公开号：WO2012019106A8

  公开（公告）日：2012-09-27
• NEUROACTIVE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Sage Therapeutics, Inc.

  公开号：US20170304321A1

  公开（公告）日：2017-10-26

  Methods for treating a subject suffering from a sterol synthesis disorder or a sterol deficiency disorder, e.g., Smith-Lemli-Opitz syndrome, the method comprising administering to the subject an effective amount of an NMDA receptor modulating compound, are provided.
• [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.
• [EN] NEUROACTIVE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS NEUROACTIFS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SAGE THERAPEUTICS INC

  公开号：WO2016057713A1

  公开（公告）日：2016-04-14

  Methods for treating a subject suffering from a sterol synthesis disorder or a sterol deficiency disorder, e.g., Smith-Lemli-Opitz syndrome, the method comprising administering to the subject an effective amount of an NMDA receptor modulating compound, are provided.
• Synthesis of a Series of Novel 3,9-Disubstituted Phenanthrenes as Analogues of Known N-Methyl-d-aspartate Receptor Allosteric Modulators
  作者：Mark Irvine、Guangyu Fang、Richard Eaves、Maria Mayo-Martin、Erica Burnell、Blaise Costa、Georgia Culley、Arturas Volianskis、Graham Collingridge、Daniel Monaghan、David Jane

  DOI：10.1055/s-0034-1380114

  日期：2015.6

  9-Substituted phenanthrene-3-carboxylic acids have been reported to have allosteric modulatory activity at the N-methyl-d-aspartate (NMDA) receptor. This receptor is activated by the excitatory neurotransmitter l-glutamate and has been implicated in a range of neurological disorders such as schizophrenia, epilepsy and chronic pain, and in neurodegenerative disorders such as Alzheimer’s disease. Herein, the convenient synthesis of a wide range of novel 3,9-disubstituted phenanthrene derivatives starting from a few common intermediates is described. These new phenanthrene derivatives will help to clarify the structural requirements for allosteric modulation of the NMDA receptor.

  9-取代菲3-羧酸据报道具有对N-甲基-d-天冬氨酸（NMDA）受体的变构调节活性。该受体被兴奋性神经递质l-谷氨酸激活，并已被认为与一系列神经系统疾病（如精神分裂症、癫痫和慢性疼痛）以及神经退行性疾病（如阿尔茨海默病）有关。本文描述了从几种常见中间体出发合成一系列新型3,9-二取代菲衍生物的便捷方法。这些新的菲衍生物将有助于阐明对NMDA受体的变构调节的结构要求。