UBP 512 | 1333112-78-9

• 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: UBP 512
• 英文别名: 9-iodophenanthrene-3-carboxylic acid；UBP512；9-iodo-3-carboxyphenanthrene
• CAS: 1333112-78-9
• 化学式: C₁₅H₉IO₂
• 分子量: 348.14
• InChiKey: HOYQQANZLZKQHU-UHFFFAOYSA-N

物化性质

• 沸点：
  502.0±25.0 °C(Predicted)
• 密度：
  1.810±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：

  UBP 512 在 氯化亚砜 、 三乙胺 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 15.0h， 生成 9-iodophenanthrene-3-carboxylic acid 2-phenethyl amide
  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
• 作为产物：
  描述：

  1-(9-溴菲-3-基)乙酮 在 正丁基锂 、 溴 、 碘 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 20.51h， 生成 UBP 512
  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

• 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.
• [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.