2-(O-氯苯氧基)-N-甲基-乙胺 | 70289-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(O-氯苯氧基)-N-甲基-乙胺
• 英文名称: [2-(2-chloro-phenoxy)-ethyl]-methyl-amine
• 英文别名: [2-(2-Chlor-phenoxy)-aethyl]-methyl-amin；Ethylamine, 2-(o-chlorophenoxy)-N-methyl-；2-(2-chlorophenoxy)-N-methylethanamine
• CAS: 70289-29-1
• 化学式: C₉H₁₂ClNO
• mdl: MFCD00018247
• 分子量: 185.653
• InChiKey: GYRWDMBVYFSMTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2922299090

反应信息

• 作为反应物：
  描述：

  1,2-双(2-溴乙氧基)乙烷 、 2-(O-氯苯氧基)-N-甲基-乙胺 以 乙腈 为溶剂， 生成 [2-(2-Chloro-phenoxy)-ethyl]-{2-[2-(2-{[2-(2-chloro-phenoxy)-ethyl]-methyl-amino}-ethoxy)-ethoxy]-ethyl}-methyl-amine
  参考文献：
  名称：

  Schnekenburger, Arzneimittel-Forschung/Drug Research, 1975, vol. 25, # 12, p. 1853 - 1858

  摘要：

  DOI：
• 作为产物：
  描述：

  邻氯苯酚 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 2-(O-氯苯氧基)-N-甲基-乙胺
  参考文献：
  名称：

  Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α_1d Adrenergic Receptor

  摘要：

  In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the aid adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially, held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three alpha(1)-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the alpha(1d)-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BAN 7378 and 69 into the putative binding sites of the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2, (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding, interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for alpha(1d) adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.

  DOI：

  10.1021/jm030944+

文献信息

• BE626725
  申请人：——

  公开号：——

  公开（公告）日：——
• Koenig; Huisgen, Chemische Berichte, 1959, vol. 92, p. 429,435
  作者：Koenig、Huisgen

  DOI：——

  日期：——
• HYDROXAMIC AND CARBOXYLIC ACID DERIVATIVES HAVING MMP AND TNF INHIBITORY ACTIVITY
  申请人：Darwin Discovery Limited

  公开号：EP1030836A1

  公开（公告）日：2000-08-30
• Inhibitors of ion channels
  申请人：ICAgen, Inc.

  公开号：EP1995241B1

  公开（公告）日：2010-03-17
• US6187924B1
  申请人：——

  公开号：US6187924B1

  公开（公告）日：2001-02-13

表征谱图