3-chloro-N-methyl-N-phenylethylpropan-1-amine | 16210-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-N-methyl-N-phenylethylpropan-1-amine
• 英文别名: N-(3-chloropropyl)-N-methylphenethylamine；N-(3-Chlorpropyl)-N-methyl-phenethylamin；3-chloro-N-methyl-N-(2-phenylethyl)propan-1-amine
• CAS: 16210-86-9
• 化学式: C₁₂H₁₈ClN
• 分子量: 211.735
• InChiKey: GAKKDLWKSVJSJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  吩噻嗪 、 3-chloro-N-methyl-N-phenylethylpropan-1-amine 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以40%的产率得到10-[3-(N-methyl-N-phenylethylamino)propyl]phenothiazine
  参考文献：
  名称：

  Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands

  摘要：

  Sigma 1 receptors are associated with neurodegenerative and psychiatric disorders. These receptors, via their chaperoning functions that counteract endoplasmic reticulum stress and block neurodegeneration, may serve as a target for a new generation of antidepressants or neuroprotective agents. The involvement of these receptors has also been observed in neuropathic pain and cancer. Only a few ligands, such as Igmesine and Anavex 2-73, have been involved in clinical trials. Thus the development of sigma 1 ligands is of interest to a new generation of drugs. Previous work in our lab underlined the potency of benzannulated bicyclic compounds as interesting ligands. Herein the work was extended to a series of novel tricyclic compounds. Carboline- and phenothiazine-derivated compounds were designed and synthesized. In vitro competition binding assays for sigma 1 and 2 receptors showed that most of them have high affinity for sigma 1 receptor (K-i = 2.5-18 nM), and selectivity toward sigma 2 receptor, without cytotoxic effects on SY5Y cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.053
• 作为产物：
  描述：

  1-溴-3-氯丙烷 、 n-甲基苯基乙胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 以65%的产率得到3-chloro-N-methyl-N-phenylethylpropan-1-amine
  参考文献：
  名称：

  Carboline- and phenothiazine-derivated heterocycles as potent SIGMA-1 protein ligands

  摘要：

  Sigma 1 receptors are associated with neurodegenerative and psychiatric disorders. These receptors, via their chaperoning functions that counteract endoplasmic reticulum stress and block neurodegeneration, may serve as a target for a new generation of antidepressants or neuroprotective agents. The involvement of these receptors has also been observed in neuropathic pain and cancer. Only a few ligands, such as Igmesine and Anavex 2-73, have been involved in clinical trials. Thus the development of sigma 1 ligands is of interest to a new generation of drugs. Previous work in our lab underlined the potency of benzannulated bicyclic compounds as interesting ligands. Herein the work was extended to a series of novel tricyclic compounds. Carboline- and phenothiazine-derivated compounds were designed and synthesized. In vitro competition binding assays for sigma 1 and 2 receptors showed that most of them have high affinity for sigma 1 receptor (K-i = 2.5-18 nM), and selectivity toward sigma 2 receptor, without cytotoxic effects on SY5Y cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.10.053

文献信息

• Phenylacetonitriles which are substituted by basic groups, their
  申请人：BASF Aktiengesellschaft

  公开号：US04968717A1

  公开（公告）日：1990-11-06

  Compounds of the formula ##STR1## where R.sup.1 to R.sup.7, m, n and p have the meanings stated in the description, and certain derivatives which are p-substituted in the left-hand phenyl ring, are useful for the treatment of disorders.

  式子##STR1##的化合物，其中R.sup.1至R.sup.7，m，n和p具有描述中所述的含义，以及在左手苯环中p-取代的某些衍生物，可用于治疗疾病。
• 1,7-Diphenyl-3-methylaza-7-cyan-8-methyl-nonan zur Verwendung bei der Bekämpfung von Krankheiten
  申请人：BASF Aktiengesellschaft

  公开号：EP0147707A2

  公开（公告）日：1985-07-10

  Die Erfindung betrifft 1,7-Diphenyl-3-methylaza-7-cyan-8-methyl-nonan sowie dessen Antipoden und Salze als Substanzen zur Bekämpfung von Krankheiten.

  本发明涉及 1,7-二苯基-3-甲基氮-7-氰基-8-甲基壬烷及其对映体和盐类，可作为防治疾病的物质。
• RASCHACK, M.;KREISKOTT, H.;SEITZ, W.
  作者：RASCHACK, M.、KREISKOTT, H.、SEITZ, W.

  DOI：——

  日期：——
• Basisch substituierte Phenylacetonitrile, ihre Herstellung und diese enthaltende Arzneimittel
  申请人：BASF Aktiengesellschaft

  公开号：EP0231003B1

  公开（公告）日：1993-04-07
• DERIVES DE CYCLOPROPYLACETONITRILE, LEUR PREPARATION ET LEUR APPLICATION COMME MEDICAMENTS
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：EP0699182A1

  公开（公告）日：1996-03-06