1-苯氧基-3-(4-苯基哌嗪基)丙烷 | 66307-58-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-苯氧基-3-(4-苯基哌嗪基)丙烷
• 英文名称: 1-(3-phenoxypropyl)-4-phenylpiperazine
• 英文别名: LASSBio-729；1-(3-phenoxy-propyl)-4-phenyl-piperazine
• CAS: 66307-58-2
• 化学式: C₁₉H₂₄N₂O
• 分子量: 296.412
• InChiKey: XHIUHIDIRNZTAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  烯丙基苯基醚 在 dimethyl sulfide borane 、 lithium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 52.0h， 生成 1-苯氧基-3-(4-苯基哌嗪基)丙烷
  参考文献：
  名称：

  Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties

  摘要：

  We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl)-4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [(3)H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (K(i) = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (K(B) = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (K(B) = 0.017 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.032

文献信息

• Agarwal, Shiv K.; Kumar, Yatendra; Saxena, Anil K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 5, p. 435 - 439
  作者：Agarwal, Shiv K.、Kumar, Yatendra、Saxena, Anil K.、Jain, Padam C.、Anand, Nitya

  DOI：——

  日期：——
• Multi-receptor drug design: Haloperidol as a scaffold for the design and synthesis of atypical antipsychotic agents
  作者：Kwakye Peprah、Xue Y. Zhu、Suresh V.K. Eyunni、Vincent Setola、Bryan L. Roth、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2011.12.019

  日期：2012.2

  Using haloperidol as a scaffold, new agents were designed to investigate the structural contributions of various groups to binding at CNS receptors associated with atypical antipsychotic pharmacology. It is clear that each pharmacophoric group, the butyrophenone, the piperidine and the 4-chlorophenyl moieties contributes to changes in binding to the receptors of interest. This strategy has resulted in the identification of several new agents, compounds 16, 18, 19, 23, 24 and 25, with binding profiles which satisfy our stated criteria for agents to act as potential atypical antipsychotics. This research demonstrates that haloperidol can serve as a useful lead in the identification and design of new agents that target multiple receptors associated with antipsychotic pharmacology. Published by Elsevier Ltd.
• The synthesis and antiallergy activity of 1-(aryloxy)-4-(4-arylpiperazinyl)-2-butanol derivatives
  作者：David A. Walsh、Ying Ho Chen、Jerry B. Green、Joseph C. Nolan、John M. Yanni

  DOI：10.1021/jm00168a044

  日期：1990.6

  A series of 1-(aryloxy)-4-(4-arylpiperazinyl)-2-butanol derivatives were prepared and evaluated for antiallergy activity in the passive foot anaphylaxis (PFA) assay in rats. Twenty-seven derivatives had activity equal to or greater than the parent, alpha-(phenoxymethyl)-4-phenyl-1-piperazinepropanol. Six derivatives that possessed greater activity in the PFA than the parent compound were then tested in the guinea pig anaphylaxis (GPA) assay. Five of the derivatives were more potent than the parent (PD50 = 40 mg/kg) in the GPA with alpha-[(4-fluorophenoxy)methyl]-4-(4-fluorophenyl)-1-piperazinepropan ol (PD50 = 3 mg/kg) having the greatest potency.
• AGARWAL, SHIV, K.;KUMAR, YATENDRA;SAXENA, ANIL, K.;JAIN, PADAM, C.;ANAND,+, INDIAN J. CHEM., 1982, 21, N 5, 435-439
  作者：AGARWAL, SHIV, K.、KUMAR, YATENDRA、SAXENA, ANIL, K.、JAIN, PADAM, C.、ANAND,+

  DOI：——

  日期：——
• Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-Adrenergic receptor blocking properties
  作者：Luiz A.S. Romeiro、Marcos da Silva Ferreira、Leandro L. da Silva、Helena C. Castro、Ana L.P. Miranda、Cláudia L.M. Silva、François Noël、Jéssica B. Nascimento、Claudia V. Araújo、Eduardo Tibiriçá、Eliezer J. Barreiro、Carlos A.M. Fraga

  DOI：10.1016/j.ejmech.2011.04.032

  日期：2011.7

  We described herein the discovery of 1-(2-(benzo[d] [1,3]dioxol-6-yl)ethyl)-4-(2-methoxyphenyl) piperazine (LASSBio-772), as a novel potent and selective alpha 1A/1D adrenoceptor (AR) antagonist selected after screening of functionalized N-phenylpiperazine derivatives in phenylephrine-induced vasoconstriction of rabbit aorta rings. The affinity of LASSBio-772 for alpha 1A and alpha 1B AR subtypes was determined through displacement of [(3)H]prazosin binding. We obtained Ki values of 0.14 nM for the alpha 1A-AR, similar to that displayed by tamsulosin (K(i) = 0.13 nM) and 5.55 nM for the alpha 1B-AR, representing a 40-fold higher affinity for alpha 1A-AR. LASSBio-772 also presented high affinity (K(B) = 0.025 nM) for the alpha 1D-AR subtype in the functional rat aorta assay, showing to be equipotent to tamsulosin (K(B) = 0.017 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.