2-(β-hydroxyethyl)-5-methoxybenzotriazole | 94120-17-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 2-(β-hydroxyethyl)-5-methoxybenzotriazole
• 英文别名: 2-(5-Methoxybenzotriazol-2-yl)ethanol；2-(5-methoxybenzotriazol-2-yl)ethanol
• CAS: 94120-17-9
• 化学式: C₉H₁₁N₃O₂
• 分子量: 193.205
• InChiKey: LZXRYARGIKGBBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(β-hydroxyethyl)-5-methoxybenzotriazole 在 三乙胺 作用下， 以 苯 为溶剂， 反应 120.0h， 生成 5-Methoxy-2-[2-(4-phenyl-piperazin-1-yl)-ethyl]-2H-benzotriazole
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes

  摘要：

  Thirteen [(aryl/heteroaryl-piperazinyl)alkyl]benzotriazoles were prepared as potential trazodone- and buspirone-like drugs. The synthesized compounds displayed from moderate to good affinity to the serotonin 5-HT1A receptor and only modest or poor affinity to the dopamine D-2 receptor, similar to buspirone. The introduction of substituents on the benzotriazole ring did,not improve the affinity to the 5-HT1A receptor, compared to the previously described unsubstituted derivatives. In a general pharmacological screening, which concerned only three of these compounds so far (5, 7 and 13), several in vitro and in vivo activities were observed.The guinea pig ileum contractions, induced either electrically or by several agonists, were strongly inhibited; at higher concentrations also the spontaneous tone of the guinea pig trachea was reduced. Compound 13 exhibited good analgesic activity in mice in the formalin-induced algesia and in the writhing test. The same at 30 mg kg(-1) p.o. also displayed antihypertensive activity probably related to calcium channel blockade and adrenergic alpha(1) antagonism. In binding assays, 13 showed a IC50 = 580 nM for displacing [H-3]prazosin from alpha(1) receptor.Finally, compound 5 (and, to a minor extent, compound 13) protected mice against potassium cyanide induced hypoxia. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01033-3
• 作为产物：
  描述：

  5-甲氧基-1H-苯并噻唑 、 2-氯乙醇 在 sodium hydroxide 作用下， 反应 3.0h， 以40%的产率得到1-(β-hydroxyethyl)-5-methoxybenzotriazole
  参考文献：
  名称：

  El-Kerdawy, Mohamed M.; Ismaiel, Abdel Kader M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 9, p. 844 - 848

  摘要：

  DOI：

文献信息

• Synthesis and pharmacological evaluation of aryl/heteroaryl piperazinyl alkyl benzotriazoles as ligands for some serotonin and dopamine receptor subtypes
  作者：Alessandro Boido、Caterina Canu Boido、Fabio Sparatore

  DOI：10.1016/s0014-827x(01)01033-3

  日期：2001.4

  Thirteen [(aryl/heteroaryl-piperazinyl)alkyl]benzotriazoles were prepared as potential trazodone- and buspirone-like drugs. The synthesized compounds displayed from moderate to good affinity to the serotonin 5-HT1A receptor and only modest or poor affinity to the dopamine D-2 receptor, similar to buspirone. The introduction of substituents on the benzotriazole ring did,not improve the affinity to the 5-HT1A receptor, compared to the previously described unsubstituted derivatives. In a general pharmacological screening, which concerned only three of these compounds so far (5, 7 and 13), several in vitro and in vivo activities were observed.The guinea pig ileum contractions, induced either electrically or by several agonists, were strongly inhibited; at higher concentrations also the spontaneous tone of the guinea pig trachea was reduced. Compound 13 exhibited good analgesic activity in mice in the formalin-induced algesia and in the writhing test. The same at 30 mg kg(-1) p.o. also displayed antihypertensive activity probably related to calcium channel blockade and adrenergic alpha(1) antagonism. In binding assays, 13 showed a IC50 = 580 nM for displacing [H-3]prazosin from alpha(1) receptor.Finally, compound 5 (and, to a minor extent, compound 13) protected mice against potassium cyanide induced hypoxia. (C) 2001 Elsevier Science S.A. All rights reserved.
• El-Kerdawy, Mohamed M.; Ismaiel, Abdel Kader M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 9, p. 844 - 848
  作者：El-Kerdawy, Mohamed M.、Ismaiel, Abdel Kader M.

  DOI：——

  日期：——