α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol | 89789-86-6

• 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: α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol
• 英文别名: alpha-[N-[2-(3-Carbamoyl-4-hydroxy-phenoxy)-ethyl]aminomethyl]-benzyl alcohol；2-hydroxy-5-[2-[(2-hydroxy-2-phenylethyl)amino]ethoxy]benzamide
• CAS: 89789-86-6
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: CCPISVXYQCVBOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯甲酰胺 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 反应 20.0h， 生成 α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-aminomethyl]-benzyl alcohol
  参考文献：
  名称：

  .beta.-Adrenergic blocking agents: substituted phenylalkanolamines. Effect of side-chain length on .beta.-blocking potency in vitro

  摘要：

  The synthesis of a group of potential beta-blockers bearing a new 5-ethoxysalicylamide substituent on nitrogen is described. These compounds were tested for beta-adrenergic blocking potency in vitro and compared with analogous compounds bearing a tert-butyl group on nitrogen. The new N-substituent increased the beta-blocking potency substantially. In a series of five homologous compounds of the type Ar(CH2)nCHOHCH2NHR (R = 5-ethoxysalicylamide; n = 0-4), two maxima of beta-blocking potency were found for n = 0 and 2. Moreover, the carbon isostere of the corresponding (aryloxy)propanolamine still proved to be a very potent beta-blocker. The ether oxygen in the side chain is therefore not an absolute requirement for activity. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00373a003

文献信息

• N-Alkylated aminoalcohols and their pharmaceutical compositions useful
  申请人：Ciba-Geigy Corporation

  公开号：US04460580A1

  公开（公告）日：1984-07-17

  The invention relates to novel N-alkylated aminoalcohols of the formula ##STR1## in which Ar is a radical of aromatic character which is unsubstituted or substituted by hydroxyl, n has the values nought or 1 and Alk is an alkylene radical having 2 to 5 carbon atoms and the nitrogen atom and the oxygen atom or, if n is nought, the salicylamide radical are separated from one another by at least two carbon atoms in the straight-chain, and their salts. The main action of the novel compounds consists in a stimulation of cardiac .beta.-receptors; the compounds also effect a blockage of adrenergic .alpha.-receptors and a lowering in the blood pressure. They can therefore be used as .beta.-stimulators, especially as agents having a positively inotropic action for the treatment of cardiac insufficiency. Compounds of the formula I in which Ar is phenyl, unsubstituted or substituted by 1 or 2 hydroxyl groups, Alk is an alkylene radical having 2 to 4 carbon atoms, n has the value 1, and the nitrogen atom and the oxygen atom are separated from one another by at least 2 carbon atoms in the straight-chain, or salts thereof, exhibit effects on the central nervous system, which are reflected for example in the suppression of the symptoms of impaired sympathetic functions and in the suppression of lack of initiative. Such compounds of the formula I therefore can be used for the treatment of reactive or endogenic states of depression of varying degrees of severity, and also for the treatment of neurotic or other psychic disturbances involving loss of initiative and depressive disorders. Such compounds can also be used for the short-term treatment of post-partum or postoperative depression, or of depression of different origin. Such compounds of the formula I can be used on their own or in combination with other antidepressants.

  该发明涉及具有以下结构的新型N-烷基化氨基醇：##STR1##其中Ar是具有芳香性质的基团，未取代或被羟基取代，n的值为零或1，Alk是具有2至5个碳原子的烷基基团，氮原子和氧原子或者，如果n为零，则是水杨酰胺基团，在直链中至少被至少两个碳原子分开，以及它们的盐。这些新型化合物的主要作用在于刺激心脏β-受体；这些化合物还会阻断肾上腺素α-受体并降低血压。因此，它们可以用作β-激动剂，特别是作为具有正性肌力作用的药物，用于治疗心脏功能不全。其中Ar为苯基，未取代或被1或2个羟基取代，Alk是具有2至4个碳原子的烷基基团，n的值为1，氮原子和氧原子在直链中至少被至少2个碳原子分开，或其盐的化合物，对中枢神经系统产生影响，例如抑制受损交感神经功能的症状和抑制缺乏主动性。因此，这些具有结构I的化合物可用于治疗不同程度的反应性或内源性抑郁状态，以及用于治疗神经症或其他涉及缺乏主动性和抑郁障碍的精神紊乱。这些化合物还可用于短期治疗产后抑郁症或术后抑郁症，或不同起源的抑郁症。这些具有结构I的化合物可以单独使用或与其他抗抑郁药物联合使用。
• 9-Aminoalkylfluorenes, process therefor and antiarrhythmic formulations thereof
  申请人：ELI LILLY AND COMPANY

  公开号：EP0018076B1

  公开（公告）日：1983-09-21
• N-Alkylierte Aminoalkohole und ihre Salze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
  申请人：CIBA-GEIGY AG

  公开号：EP0005848B1

  公开（公告）日：1981-12-30
• US4277495A
  申请人：——

  公开号：US4277495A

  公开（公告）日：1981-07-07
• US4382093A
  申请人：——

  公开号：US4382093A

  公开（公告）日：1983-05-03