4-(2-chloroethyl)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl-methyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 4-(2-chloroethyl)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl-methyl)piperidine
• 英文别名: 4-(2-Chloroethyl)-1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)piperidine
• 化学式: C₁₆H₂₂ClNO₂
• 分子量: 295.809
• InChiKey: ZVARLYFCMMJNBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-chloroethyl)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl-methyl)piperidine 在 lithium aluminium tetrahydride 、 potassium iodide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 3-[1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl]propylamine
  参考文献：
  名称：

  New Substituted 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl Derivatives with α₂-Adrenoceptor Antagonist Activity

  摘要：

  The emergence of a novel theory concerning the role of noradrenaline in the progression and the treatment of neurodegenerative diseases such as Parkinson's and Alzheimer's diseases has provided a new impetus toward the discovery of novel compounds acting at alpha(2)-adrenoceptors. A series of substituted 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl) piperidin-4-yl derivatives bearing an amide, urea, or imidazolidinone moiety was studied. Some members of this series of compounds proved to be potent alpha(2)-adrenoceptor antagonists with good selectivity versus alpha(1)-adrenergic and D(2)-dopamine receptors. Particular emphasis is given to compound 33g which displays potent alpha(2)-adrenoceptor binding affinity in vitro and central effects in vivo following oral administration.

  DOI：

  10.1021/jm991121g

文献信息

• [EN] NOVEL PIPERIDINE DERIVATIVES 4-SUBSTITUTED BY AN IMIDAZOLIDIN-2-ON-1-YL-ETHYL, TETRAHYDROPYRIMIDIN-2-ON-1-YL-ETHYL AND 1,3-DIAZEPIN-2-ON-1-YL-ETHYL GROUP, AND USE THEREOF AS alpha 2-ADRENERGIC RECEPTOR ANTAGONISTS<br/>[FR] NOUVEAUX DERIVES DE LA PIPERIDINE SUBSTITUES EN POSITION 4 PAR UN GROUPE IMIDAZOLIDIN-2-ON-1-YL-ETHYL, TETRAHYDROPYRIMIDIN-2-ON-1-YL-ETHYL, ET 1,3-DIA-ZEPIN-2-ON-1-YL-ETHYL, ET LEURS APPLICATIONS COMME ANTAGONISTES DES RECEPTEURS ALPHA-2 ADRENERGIQUES
  申请人：PIERRE FABRE MEDICAMENT

  公开号：WO1997028157A1

  公开（公告）日：1997-08-07

  (EN) Novel cyclic urea derivatives of 4-ethyl piperidine having general formula 1, wherein R1 is a (1,4-benzodioxan-2-yl)methyl group, a (2-H)-benzopyrane-3-yl methyl group or a 4-(chromanone-2-yl)methyl group; R4 is a hydrogen atom, a C1-4 alkyl chain or an optionally substituted aryl, heteroaryl, aralkyl or naphthyl ring; n is 0, 1 or 2; and R2 and R3 are either hydrogen atoms or a benzo residue fused to the cyclic urea system; salts thereof and preparation methods therefor, are disclosed. The use of such compounds as a drug, pharmaceutical compositions containing same, and preparation methods therefor, are also disclosed.(FR) La présente invention concerne les nouveaux dérivés urées cycliques de 4-éthyl pipéridine répondant à la formule générale 1, où R1 représente un groupe (1,4-benzodioxan-2-yl)méthyl, un groupe (2-H)-benzopyrane-3-yl méthyl, ou un groupe 4-(chromanone-2-yl)méthyl, R4 représente soit un atome d'hydrogène, une chaîne alkyl en C1-4, un noyau aryl, hétéroaryl, aralkyl, ou naphtyl, éventuellement substitués, n peut prendre les valeurs 0, 1 ou 2, R2 et R3 représentent, soit des atomes d'hydrogène, soit un reste benzo fusionné avec le système urée cyclique, leurs formes salifiées et leurs procédés de préparation. Elle concerne aussi l'utilisation de ces composés à titre de médicament, et les compositions pharmaceutiques les comprenant, et leurs procédés de préparation.
• New Substituted 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidin-4-yl Derivatives with α₂-Adrenoceptor Antagonist Activity
  作者：Patrice Mayer、Pascale Brunel、Céline Chaplain、Christel Piedecoq、Francis Calmel、Philippe Schambel、Philippe Chopin、Thierry Wurch、Petrus J. Pauwels、Marc Marien、Jean-Louis Vidaluc、Thierry Imbert

  DOI：10.1021/jm991121g

  日期：2000.10.1

  The emergence of a novel theory concerning the role of noradrenaline in the progression and the treatment of neurodegenerative diseases such as Parkinson's and Alzheimer's diseases has provided a new impetus toward the discovery of novel compounds acting at alpha(2)-adrenoceptors. A series of substituted 1-(2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl) piperidin-4-yl derivatives bearing an amide, urea, or imidazolidinone moiety was studied. Some members of this series of compounds proved to be potent alpha(2)-adrenoceptor antagonists with good selectivity versus alpha(1)-adrenergic and D(2)-dopamine receptors. Particular emphasis is given to compound 33g which displays potent alpha(2)-adrenoceptor binding affinity in vitro and central effects in vivo following oral administration.