PHCCC | 179068-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: PHCCC
• 英文别名: (7E)-7-hydroxyimino-N-phenyl-1,7a-dihydrocyclopropa[b]chromene-1a-carboxamide
• CAS: 179068-02-1
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: FPXPIEZPAXSELW-CYVLTUHYSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P301+P312+P330
• 危险性描述：
  H302

制备方法与用途

生物活性

PHCCC 是一种 I 型 mGluR (Group I mGluR) 拮抗剂，IC50 为 3 μM，PHCCC 也是 mGlu4 受体选择性正向调节剂。具有抗帕金森病作用。

靶点

Group I mGluR receptors 3 μM (IC 50 )

体外研究

PHCCC potentiated the effect of L-(+)-2-amino-4-phosphonobutyric acid (L-AP4) in inhibiting transmission at the striatopallidal synapse.

体内研究

PHCCC (75 nmol/2.5 μl; intracerebroventricular) produces an antiparkinsonian effect in a dopamine depletion akinesia model.

反应信息

• 作为产物：
  描述：

  2-Oxo-1a,2-dihydro-1H-7-oxa-cyclopropa[b]naphthalene-7a-carboxylic acid phenylamide 在 盐酸羟胺 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到PHCCC
  参考文献：
  名称：

  A novel class of antagonists for metabotropic glutamate receptors, 7-(Hydroxyimino)cyclopropa[b]chromen-1a-carboxylates

  摘要：

  7-(Hydroxyimino)cyclopropa[b] chromen-1a-carboxylates (4a-c), highly potent antagonists for a phospholipase C-linked metabotropic glutamate receptor, mGluR1, were synthesized through cyclopropanation onto 4-oxo-4H-1-benzopyran-2-carboxylates (5a-c) utilizing dimethyloxosulfonium methylid followed by treatment with hydroxylamine. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00104-7

文献信息

• [EN] ALLOSTERIC MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] MODULATEURS ALLOSTÉRIQUES DES RÉCEPTEURS MÉTABOTROPIQUES DU GLUTAMATE
  申请人：MERCK SHARP & DOHME

  公开号：WO2013063100A1

  公开（公告）日：2013-05-02

  Disclosed are compounds of Formula (I), and salts thereof, wherein R1, RA2, RA3 and RA4, are defined herein, which have properties for positive allosteric modulation of mGluR-4 receptor sites. Also described are pharmaceutical formulations comprising the compounds of Formula (I) or their salts, and methods of treating Parkinson's disease and related disorders using the same.

  揭示了式（I）的化合物及其盐，其中R1、RA2、RA3和RA4在此有定义，具有对mGluR-4受体位点进行正向变构的特性。还描述了包含式（I）的化合物或其盐的药物配方，以及使用它们治疗帕金森病和相关疾病的方法。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Kõster Hubert

  公开号：US20100248264A1

  公开（公告）日：2010-09-30

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了捕获化合物及其集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• CYCLOPROPACHROMENECARBOXYLATE DERIVATIVES
  申请人：SUNTORY LIMITED

  公开号：EP0787723A1

  公开（公告）日：1997-08-06

  The present invention provides novel cyclopropachromencarboxylic acid derivatives having an antagonistic activity against metabotropic glutamate receptors and its pharmaceutically acceptable salts. Cyclopropachromencarboxylic acid derivatives and its pharmaceutically acceptable salts represented by the following general formula (1): [wherein A denotes an oxygen atom, hydroxyimino group, an alkyloxyimino group having 1 to 5 carbon atoms, or the group =N-O-(CH2)n-NR1R2 (where n represents an integer of 2 to 8, and each of R1 and R2 independently represents a hydrogen atom or alkyl group having 1 to 5 carbon atoms, respectively); B denotes the group -COOR3(where R3 represents a hydrogen atom or alkyl group having 1 to 5 carbon atoms) or the group -CONR4R5 (where R4 and R5 independently represent a hydrogen atom, alkyl group having 1 to 5 carbon atoms, alkenyl group having 2 to 5 carbon atoms, aminoalkyl group having 1 to 5 carbon atoms wherein N may be substituted, nitrogen-containing saturated heterocycle of which N may be substituted, phenyl group which may be substituted with a halogen atom or hydroxyl group which in turn may be substituted, 2-pyridyl group, or aralkyl group having 7 to 10 carbon atoms, or R4and R5 taken together with the nitrogen atom to which they are attached form a nitrogen-containing heterocyclic ring-system which may be substituted); and X is a halogen atom or the group -OR6(where R6 represents a hydrogen atom, alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms)].

  本发明提供了对代谢型谷氨酸受体具有拮抗活性的新型环丙色羧酸衍生物及其药学上可接受的盐类。由以下通式（1）代表的环丙基色羧酸衍生物及其药学上可接受的盐： [其中 A 表示氧原子、羟基亚氨基、具有 1 至 5 个碳原子的烷氧基亚氨基或基团 =N-O-(CH2)n-NR1R2（其中 n 代表 2 至 8 的整数，R1 和 R2 分别独立地代表氢原子或具有 1 至 5 个碳原子的烷基）； B 表示基团 -COOR3（其中 R3 代表氢原子或具有 1 至 5 个碳原子的烷基）或基团 -CONR4R5（其中 R4 和 R5 分别独立地代表氢原子、具有 1 至 5 个碳原子的烷基、具有 2 至 5 个碳原子的烯基、具有 1 至 5 个碳原子的氨基烷基，其中 N 可被取代、其中 N 可被取代的含氮饱和杂环，可被卤素原子或羟基取代的苯基，可被取代的 2-吡啶基，或具有 7 至 10 个碳原子的芳烷基，或 R4 和 R5 与它们所连接的氮原子一起形成可被取代的含氮杂环环系）；和 X 是卤素原子或基团-OR6（其中 R6 代表氢原子、具有 1 至 5 个碳原子的烷基、具有 3 至 6 个碳原子的烯基或具有 7 至 10 个碳原子的芳基）]。
• US8569481B2
  申请人：——

  公开号：US8569481B2

  公开（公告）日：2013-10-29
• US9034798B2
  申请人：——

  公开号：US9034798B2

  公开（公告）日：2015-05-19