1-(benzothiophen-5-yl)-2-<2-(N,N-diethylamino)ethoxy>ethanol | 392233-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1-(benzothiophen-5-yl)-2-<2-(N,N-diethylamino)ethoxy>ethanol
• 英文别名: (R,S)-1-(benzo[b]thiophen-5-yl)-2-[2-(N,N-diethylamino)ethoxy]ethanol；(-)-1-(benzo[b]thiophen-5-yl)-2-[2-(N,N-diethylamino)ethoxy]ethanol；1-(1-Benzothiophen-5-yl)-2-[2-(diethylamino)ethoxy]ethanol
• CAS: 392233-08-8
• 化学式: C₁₆H₂₃NO₂S
• 分子量: 293.43
• InChiKey: KJUIRLKBYFDLAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(benzothiophen-5-yl)-2-<2-(N,N-diethylamino)ethoxy>ethanol 生成 Acetic acid 1-benzo[b]thiophen-5-yl-2-(2-diethylamino-ethoxy)-ethyl ester
  参考文献：
  名称：

  Biol. Pharm. Bull. 1995, 18, 1779-1783

  摘要：

  DOI：
• 作为产物：
  描述：

  二乙氨基乙醇 、 5-(1,2-epoxyethyl)benzothiophene 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 1-(benzothiophen-5-yl)-2-<2-(N,N-diethylamino)ethoxy>ethanol
  参考文献：
  名称：

  Studies on Cognitive Enhancing Agents. III. Antiamnestic and Antihypoxic Activities of a Series of l-Bicycloaryl-2-(.OMEGA.-aminoalkoxy)ethanols.

  摘要：

  双环芳烃（萘、噻吊、苯并呋喃和吲哚）的2-(2-氨基乙氧基)-1-羟乙基衍生物被制备并筛选出具有抗遗忘（AA）和抗缺氧（AH）活性的化合物。这些活性通过测定逆转电休克诱导的遗忘和保护小鼠免受缺氧影响的效力来评估。化合物3o，1-(苯并[b]噻吩-5-基)-2-(2-二乙基氨基乙氧基)乙醇，显示出最佳的AA和AH活性特征，优于我们的原型化合物，2-(2-二甲基氨基乙氧基)-1-苯乙醇（1）。在3o的侧链中延长乙烯链接到3-和4-碳单元，显著降低了AH活性。化合物3o进一步研究了其对Co2诱导记忆障碍的保护作用和在小鼠中的急性毒性。在逆转遗忘试验中，其效力是他克林的十倍，并且毒性远低于他克林。

  DOI：

  10.1248/cpb.43.1492

文献信息

• A New Cognition-Enhancing Agent, (R)-(-)-1-(Benzo(b)thiophen-5-yl)-2-(2-(N,N-diethylamino)ethoxy)ethanol Hydrochloride. Effects on Memory Impairment in Rats Generated by Cerebral Embolization and Basal Forebrain Lesions.
  作者：Satoshi ONO、Tetsuo YAMAFUJI、Hisaaki CHAKI、Yozo TODO、Mutsuko MAEKAWA、Kazunori KITAMURA、Tatsuo KIMURA、Yasushi NAKADA、Kuniko MOZUMI、Hirokazu NARITA

  DOI：10.1248/bpb.18.1779

  日期：——

  The title compound (T-588) has been evaluated for its ameliorating effect on memory impairment generated by cerebral embolization and by a basal forebrain (BF) lesion in male Wistar rats. The memory and learning deficits induced by injection of carbon-microspheres into the internal carotid artery were significantly improved by T-588 at oral dose of 3-10 mg/kg, as determined by an active avoidance response assay, whereas the reference drugs (tacrine, idebenone and indeloxazine) proved almost inactive in the same assay procedure. As far as the embolization was concerned, a significant decrease in cerebral acetylcholine and monoamines was observed. The effect on the memory impairment caused by an electrolytic lesion of the BF was assessed by a passive avoidance task. T-588 exhibited a bell-shaped dose-response curve and was most active at 1 mg/kg (oral dose), while tacrine showed equal activity at 10 mg/kg.

  对标题化合物（T-588）进行了评估，以确定其对雄性Wistar大鼠因脑栓塞和基底前脑（BF）损伤引起的记忆障碍的改善作用。通过主动回避反应测定法发现，口服剂量为3-10 mg/kg的T-588可显著改善因向颈内动脉注射碳微球引起的记忆和学习障碍，而对照药物（他克林、艾地苯醌和吲哚洛辛）在相同的测定程序中几乎无效。就栓塞而言，观察到脑乙酰胆碱和单
• Agent for potentiating nerve growth factor activity containing 1,2-ethanediol derivative or salt thereof
  申请人：TOYAMA CHEMICAL CO., LTD.

  公开号：EP1020427A1

  公开（公告）日：2000-07-19

  A remedy for diseases caused by degeneration of central or peripheral nervous system, comprising a 1,2-ethanediol derivative represented by the following general formula or its salt: wherein R1 represents a substituted or unsubstituted phenyl, naphthyl, indanyl, indenyl, tetrahydronaphthyl or heterocyclic group; R2 represents a hydrogen atom, a lower alkyl group or a hydroxyl-protecting group; R3 represents a hydrogen atom or a lower alkyl group; nR4's may be the same as or different from one another and each represents a hydrogen atom or a lower alkyl group; nR5's may be the same as or different from one another and each represents a hydrogen atom or a lower alkyl group; R6 represents a substituted or unsubstituted amino or nitrogen-containing heterocyclic group or an ammonio group; and n represents 0 or an integer of 1 to 6.

  一种治疗由中枢或周围神经系统退化引起的疾病的药物，由通式如下的1,2-乙二醇衍生物或其盐组成： 其中 R1 代表取代或未取代的苯基、萘基、茚基、茚满基、四氢萘基或杂环基团；R2 代表氢原子、低级烷基或羟基保护基团；R3 代表氢原子或低级烷基；nR4 可以相同或不同，且各代表氢原子或低级烷基；nR5 可以相同或互不相同，各自代表氢原子或低级烷基； R6 代表取代或未取代的氨基或含氮杂环基团或氨基团；以及 n 代表 0 或 1-6 的整数。
• MEDICINAL COMPOSITIONS IMPROVING BRAIN FUNCTION AND METHOD FOR IMPROVING BRAIN FUNCTION
  申请人：TOYAMA CHEMICAL CO., LTD.

  公开号：EP1514542A1

  公开（公告）日：2005-03-16

  An alkyl ether derivative represented by the formula: wherein R1, R2, R3, R4, m and n are as defined in the specification, or salts thereof exhibits synergistically improved anti-hypoxic activity when combined with a compound having an acetylcholine esterase inhibitory activity. Therefore, the combination according to the present invention is useful as a method for improving cerebral function. Further, a pharmaceutical composition containing the compound relating to the combination according to the present invention is useful for treatment and prevention of dysfunction of cerebral acetylcholine neurons in the sequelae of cerebrovascular dementia, senile dementia, Alzheimer's disease and ischemic cerebral lesion and in the cerebral apoplexy or the memory impairment caused by selective neuronal death.

  一种由式表示的烷基醚衍生物： 其中 R1、R2、R3、R4、m 和 n 如说明书中所定义，或其盐类与具有乙酰胆碱酯酶抑制活性的化合物结合使用时，可协同提高抗缺氧活性。因此，根据本发明的组合物可用作改善脑功能的方法。此外，含有与根据本发明的组合物有关的化合物的药物组合物可用于治疗和预防脑血管性痴呆、老年性痴呆、阿尔茨海默病和缺血性脑损伤后遗症中的脑乙酰胆碱神经元功能障碍，以及由选择性神经元死亡引起的脑中风或记忆障碍。
• Medicinal composition for improving brain function
  申请人：TOYAMA CHEMICAL CO., LTD.

  公开号：EP2389937A1

  公开（公告）日：2011-11-30

  Use of a following ingredients in combination for use in the treatment or prevention of dysfunction of cerebral acetylcholine neurons in the sequela of cerebrovascular dementia, senile dementia, Alzheimer's disease, ischemic cerebral lesion and cerebral apoplexy or the memory impairment caused by selective neuronal death: Ingredient (A): an alkyl ether derivative represented by the following formula: wherein either (R1 represents a benzothienyl group; R2 represents a hydrogen atom; R3 and R4, each represents a C1-6alkyl group which is optionally substituted with a hydroxyl group; R3 and R4, taken conjointly with the nitrogen atom to which R3 and R4 are linked, form an azetidine ring which is optionally substituted with a hydroxyl group; m represents an integer of 1; and n represents an integer of 3); or a salt thereof, Ingredient (B) : Tacrine or Donepezil for the manufacture of a pharmaceutical composition.

  将下列成分混合使用，用于治疗或预防脑血管痴呆、老年痴呆、阿尔茨海默病、缺血性脑损伤和脑中风后遗症中的脑乙酰胆碱神经元功能障碍或选择性神经元死亡引起的记忆障碍： 成分（A）： 由下式代表的烷基醚衍生物： 其中 (R1 代表苯并噻吩基团； R2 代表氢原子 R3和R4各自代表一个被羟基任选取代的C1-6烷基； R3 和 R4 与 R3 和 R4 所连接的氮原子共同形成氮杂环丁烷环，该环可选择被羟基取代； m 代表 1 的整数；以及 n 代表 3 的整数） 或其盐、 成分 (B) ： 他克林或 多奈哌齐 用于制造药物组合物。
• Medicinal compositions improving brain function and method for improving brain function
  申请人：Nakada Yasushi

  公开号：US20050250843A1

  公开（公告）日：2005-11-10

  An alkyl ether derivative represented by the formula: wherein R 1 , R 2 , R 3 , R 4 , m and n are as defined in the specification, or salts thereof exhibits synergistically improved anti-hypoxic activity when combined with a compound having an acetylcholine esterase inhibitory activity. Therefore, the combination according to the present invention is useful as a method for improving cerebral function. Further, a pharmaceutical composition containing the compound relating to the combination according to the present invention is useful for treatment and prevention of dysfunction of cerebral acetylcholine neurons in the sequelae of cerebrovascular dementia, senile dementia, Alzheimer's disease and ischemic cerebral lesion and in the cerebral apoplexy or the memory impairment caused by selective neuronal death.

  一种烷基醚衍生物，由以下式子表示 其中 R 1 , R 2 , R 3 , R 4 m和n如说明书中所定义，或其盐类与具有乙酰胆碱酯酶抑制活性的化合物结合使用时，可协同提高抗缺氧活性。因此，根据本发明的组合物可用作改善脑功能的方法。此外，含有与根据本发明的组合物有关的化合物的药物组合物可用于治疗和预防脑血管性痴呆、老年性痴呆、阿尔茨海默病和缺血性脑损伤后遗症中的脑乙酰胆碱神经元功能障碍，以及由选择性神经元死亡引起的脑中风或记忆障碍。