1-(3,4-Methylendioxy-benzyl)-4-phenyl-piperazin | 67361-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(3,4-Methylendioxy-benzyl)-4-phenyl-piperazin
• 英文别名: 1-Phenyl-4-(3,4-methylendioxy-benzyl)-piperazin；1-((benzo[d] [1,3]dioxol-5-yl)methyl)-4-phenylpiperazine；LASSBio-719A；1-benzo[1,3]dioxol-5-ylmethyl-4-phenyl-piperazine；1-(1,3-Benzodioxol-5-ylmethyl)-4-phenylpiperazine
• CAS: 67361-21-1
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: ZKSRSKFDFAONDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  24.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,4-Methylendioxy-benzyl)-4-phenyl-piperazin 、 4-phenyl-4-(1-phenylvinyl)-1,3-dioxolan-2-one 在 [4,4′-di-tert-butyl-2,2′-bipyridine]bis[5-methyl-2-(4-methyl-2pyridinyl)phenyl]iridium(III) hexafluorophosphate 、 sodium acetate 作用下， 以 水 、 二甲基亚砜 为溶剂， 以82 %的产率得到(Z)-4-(4-(benzo[d][1,3]dioxol-5-ylmethyl)-1-phenylpiperazin-2-yl)-2,3-diphenylbut-2-en-1-ol
  参考文献：
  名称：

  一种简便的自由基脱羧合成立体全碳四取代烯烃的方法

  摘要：

  据报道，使用各种α-氨基自由基前体和杂环作为底物，基于自由基的光催化脱羧形成立体定义的三取代和四取代烯烃。这种用户友好的方案结合了广泛的结构范围、简单的药物和合成后操作以及两种反应伙伴的变化。机理研究揭示了实现整体转变的关键CO 2挤出步骤。

  DOI：

  10.1002/anie.202403651
• 作为产物：
  描述：

  胡椒醛 、 N-苯基哌嗪 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.57h， 以90%的产率得到1-(3,4-Methylendioxy-benzyl)-4-phenyl-piperazin
  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

• COMPOUNDS FOR MODULATING T-CELLS
  申请人：Trede Nikolaus S.

  公开号：US20080293739A1

  公开（公告）日：2008-11-27

  Disclosed are compounds and compositions that modulate T-cells. Such compounds can be used to treat T-cell mediated disease like T-ALL, rheumatoid arthritis, multiple sclerosis, and graft-vs-host disease (GvHD), to name but a few. The compounds have a general structure as shown in Formula I. Ar 1 -L-Ar 2 I wherein Ar 1 and Ar 2 , are independent of one another, a substituted aryl, unsubstituted aryl, substituted heteroaryl, or unsubstituted heteroaryl; and L is a bond or a linker spanning two, three, four, or five atoms.
• US8039505B2
  申请人：——

  公开号：US8039505B2

  公开（公告）日：2011-10-18
• 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.
• An Expedient Radical Approach for the Decarboxylative Synthesis of Stereodefined All‐Carbon Tetrasubstituted Olefins
  作者：Qian Zeng、Nirwan Yamini、Jordi Benet-Buchholz、Arjan Willem Kleij

  DOI：10.1002/anie.202403651

  日期：——

  A radical-based, photo-catalyzed decarboxylative formation of stereodefined tri- and tetrasubstituted olefins is reported using various α-amino radical precursors and heterocycles as substrates. This user-friendly protocol combines a wide structural scope, easy drug and postsynthetic manipulations, and variation in both reaction partners. The mechanistic studies reveal a key CO2 extrusion step to enable

  据报道，使用各种α-氨基自由基前体和杂环作为底物，基于自由基的光催化脱羧形成立体定义的三取代和四取代烯烃。这种用户友好的方案结合了广泛的结构范围、简单的药物和合成后操作以及两种反应伙伴的变化。机理研究揭示了实现整体转变的关键CO 2挤出步骤。