N-(2-苯氧基乙基)-二(2-氯乙基)胺盐酸盐

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-(2-苯氧基乙基)-二(2-氯乙基)胺盐酸盐
• 英文名称: bis(2-chloroethyl)(2-phenoxyethyl)amine hydrochloride
• 英文别名: N,N-bis(2-chloroethyl)-2-phenoxyethanamine;hydron;chloride
• 化学式: C₁₂H₁₇Cl₂NO*ClH
• 分子量: 298.64
• InChiKey: DYFSUYTZMUXBJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-苯氧基乙基)-二(2-氯乙基)胺盐酸盐 在 sodium hydroxide 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 88.0h， 生成 4-(4-methoxy-benzenesulfonyl)-1-(2-phenoxy-ethyl)-piperidine-4-carboxylic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of N-Substituted 4-Arylsulfonylpiperidine-4-hydroxamic Acids as Novel, Orally Active Matrix Metalloproteinase Inhibitors for the Treatment of Osteoarthritis

  摘要：

  The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. In our preceding paper, we have reported on a series of novel and orally active N-hydroxy-alpha-phenylsulfonylacetamide derivatives. However, these compounds had two drawbacks (moderate selectivity and chirality issues). To circumvent these two problems, a series of novel and orally active N-substituted 4-benzenesulfonylpiperidine-4-carboxylic acid hydroxyamide derivatives have been synthesized. The present paper deals with the synthesis and SAR of these compounds. Among the several compounds synthesized, derivative 55 turned out to be a potent, selective, and an orally active MMP inhibitor in the clinically relevant advanced rabbit osteoarthritis model. Detailed pharmacokinetics and metabolism data are described.

  DOI：

  10.1021/jm0205550
• 作为产物：
  描述：

  2-[(2-Hydroxy-ethyl)-(2-phenoxy-ethyl)-amino]-ethanol 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以100%的产率得到N-(2-苯氧基乙基)-二(2-氯乙基)胺盐酸盐
  参考文献：
  名称：

  [EN] PIPERIDINE AND PIPERAZINE DERIVATIVES
  [FR] DÉRIVÉS DE PIPÉRIDINE ET DE PIPÉRAZINE

  摘要：

  公开号：

  WO2008096189A3

文献信息

• Piperidine and piperazine derivatives
  申请人：Sun Connie L.

  公开号：US20110281890A1

  公开（公告）日：2011-11-17

  Compounds of general formula (I) in which R 1 , m, X, n, Y and R 3 have any of the meanings given in the specification, have affinity for sigma receptors and are useful in the treatment of disorders of the central nervous system.

  通式(I)的化合物，在该式中R1、m、X、n、Y和R3可以是规范中所给出的任何含义，具有与sigma受体的亲和力，并可用于治疗中枢神经系统的疾病。
• Piperidine and Piperazine Derivatives
  申请人：Sun Connie L.

  公开号：US20100137334A1

  公开（公告）日：2010-06-03

  Compounds of general formula (Ia): in which R 1 , A 1 , m, X, n, Y and R 3 have any of the meanings given in the specification, have affinity for sigma receptors and are useful in the treatment of disorders of the central nervous system.

  通式（Ia）的化合物：其中R1，A1，m，X，n，Y和R3具有规范中给出的任何含义，具有对sigma受体的亲和力，并且在治疗中枢神经系统紊乱方面是有用的。
• Piperazine and Piperidine Derivatives
  申请人：Sun Connie L

  公开号：US20100256162A1

  公开（公告）日：2010-10-07

  Compounds of general formula (I) in which R 1 , m, X, n, Y and R 3 have any of the meanings given in the specification, have affinity for sigma receptors and are useful in the treatment of disorders of the central nervous system.

  通式(I)中R1、m、X、n、Y和R3具有规范中给定的任何含义的化合物具有与sigma受体的亲和力，并且在治疗中枢神经系统疾病方面是有用的。
• WO2007/89462
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Structure−Activity Relationship of N-Substituted 4-Arylsulfonylpiperidine-4-hydroxamic Acids as Novel, Orally Active Matrix Metalloproteinase Inhibitors for the Treatment of Osteoarthritis
  作者：Venkatesan Aranapakam、Jamie M. Davis、George T. Grosu、Baker、John Ellingboe、Arie Zask、Jeremy I. Levin、Vincent P. Sandanayaka、Mila Du、Jerauld S. Skotnicki、John F. DiJoseph、Amy Sung、Michele A. Sharr、Loran M. Killar、Thomas Walter、Guixian Jin、Rebecca Cowling、Jeff Tillett、Weiguang Zhao、Joseph McDevitt、Zhang Bao Xu

  DOI：10.1021/jm0205550

  日期：2003.6.1

  The matrix metalloproteinases (MMPs) are a family of zinc-containing endopeptidases that play a key role in both physiological and pathological tissue degradation. In our preceding paper, we have reported on a series of novel and orally active N-hydroxy-alpha-phenylsulfonylacetamide derivatives. However, these compounds had two drawbacks (moderate selectivity and chirality issues). To circumvent these two problems, a series of novel and orally active N-substituted 4-benzenesulfonylpiperidine-4-carboxylic acid hydroxyamide derivatives have been synthesized. The present paper deals with the synthesis and SAR of these compounds. Among the several compounds synthesized, derivative 55 turned out to be a potent, selective, and an orally active MMP inhibitor in the clinically relevant advanced rabbit osteoarthritis model. Detailed pharmacokinetics and metabolism data are described.