2-(2-溴乙氧基)-1,4-二氯苯 | 85262-50-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2-溴乙氧基)-1,4-二氯苯
• 英文名称: 1-(2-bromoethoxy)-2,5-dichlorobenzene
• 英文别名: 1-bromo-2-(2,5-dichlorophenoxy)ethane；(2-bromo-ethyl)-(2,5-dichloro-phenyl)-ether；(2-Brom-aethyl)-(2,5-dichlor-phenyl)-aether；2-(2-Bromoethoxy)-1,4-dichlorobenzene
• CAS: 85262-50-6
• 化学式: C₈H₇BrCl₂O
• mdl: MFCD02030849
• 分子量: 269.953
• InChiKey: JFOWYGCPBNNSHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  2-(2-溴乙氧基)-1,4-二氯苯 在 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2,5-dichloro-phenoxy)-ethylamine
  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+
• 作为产物：
  描述：

  2,5-二氯苯酚 、 1,2-二溴乙烷 在 sodium hydroxide 作用下， 反应 7.0h， 以52%的产率得到2-(2-溴乙氧基)-1,4-二氯苯
  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

• The multiobjective based design, synthesis and evaluation of the arylsulfonamide/amide derivatives of aryloxyethyl- and arylthioethyl- piperidines and pyrrolidines as a novel class of potent 5-HT7 receptor antagonists
  作者：Paweł Zajdel、Rafał Kurczab、Katarzyna Grychowska、Grzegorz Satała、Maciej Pawłowski、Andrzej J. Bojarski

  DOI：10.1016/j.ejmech.2012.07.043

  日期：2012.10

  An analysis of the virtual combinatorial library was used for refining a pilot set of 34 derivatives and designing a targeted 38-member library of the arylamide and arylsulfonamide derivatives of aryloxyethyl- and arylthioethyl-piperidines and pyrrolidines. All compounds 24-95 were synthesized according to an elaborated parallel solid-phase method and were biologically evaluated for their affinity for 5-HT7R. Additionally, the targeted library members were tested for 5-HT1A, 5-HT6, and D-2 receptors. Selected compounds of particular interest were examined for their intrinsic activity at 5-HT7R in vitro employing a cAMP assay. The study allowed us to identify compound 68 (4-fluoro-N-(1-2-[(propan-2-yl)phenoxylethyl}piperidin-4-yl) benzenesulfonamide) as a potent 5-HT7R ligand (K-i = 0.3 nM) with strong antagonistic properties (K-b = 1 nM) and a 1450-fold selectivity over 5-HT(1A)Rs. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Schenbor et al., Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya, 1959, vol. 2, p. 215
  作者：Schenbor et al.

  DOI：——

  日期：——
• US3235597
  申请人：——

  公开号：——

  公开（公告）日：——
• FR1481052
  申请人：——

  公开号：——

  公开（公告）日：——
• Tribological behaviour of steel-alumina sliding pairs under boundary lubrication conditions
  作者：D.-H. Hwang、K.-H. Zum Ghar

  DOI：10.1002/tt.3020090304

  日期：2003.3

  AbstractThe tribological behaviour of oil‐lubricated steel‐alumina sliding pairs was investigated using a ball‐on‐disc tribometer at room temperature. Commercial bearing balls of 10 mm diameter were mated to 99.7% Al2O3 discs, and additive‐free mineral oil was fed into the contact area. The sliding speed and the applied normal load were varied, and the initial surface roughness of the Al2O3 disc was altered using different polishing and grinding procedures. The results showed that the surface roughness of the ceramic discs dominated the tribological behaviour under the given experimental conditions. The sliding speed as well as the normal load showed less effect on the friction behaviour, but the amount of wear depended strongly on the normal load. From the results it was concluded that improvement of the surface roughness and optimised surface machining of the ceramic material can be essential for improving the tribological performance for boundary‐lubricated steel‐ceramic sliding pairs.