2-naphthyl-2-ylmethyl-bis(2-chloroethyl)amine hydrochloride | 67684-82-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthyl-2-ylmethyl-bis(2-chloroethyl)amine hydrochloride
• 英文别名: bis-(2-chloro-ethyl)-[2]naphthylmethyl-amine; hydrochloride；Bis-(2-chlor-aethyl)-[2]naphthylmethyl-amin; Hydrochlorid；2-chloro-N-(2-chloroethyl)-N-(naphthalen-2-ylmethyl)ethanamine；2-chloro-N-(2-chloroethyl)-N-(naphthalen-2-ylmethyl)ethanamine;hydrochloride
• CAS: 67684-82-6
• 化学式: C₁₅H₁₇Cl₂N*ClH
• 分子量: 318.674
• InChiKey: FMPZLSPZDMGCKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  3.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-naphthyl-2-ylmethyl-bis(2-chloroethyl)amine hydrochloride 在 sodium hydroxide 、 草酰氯 、 18-冠醚-6 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 89.0h， 生成
  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-hydroxyethyl)(2-naphthyl-2-ylmethyl)amino]ethanol hydrochloride 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以79%的产率得到2-naphthyl-2-ylmethyl-bis(2-chloroethyl)amine hydrochloride
  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

文献信息

• Lewschina; Sergiewskaja, Zhurnal Obshchei Khimii, 1954, vol. 24, p. 905,907; engl. Ausg. S. 905
  作者：Lewschina、Sergiewskaja

  DOI：——

  日期：——