4-(benzothiophen-3-yl)-1,2,3,6-tetrahydropyridine | 332387-44-7

• 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: 4-(benzothiophen-3-yl)-1,2,3,6-tetrahydropyridine
• 英文别名: 4-(3-benzo(b)thiophene)-1,2,3,6-tetrahydropyridine；4-benzo[b]thiophen-3-yl-1,2,3,6-tetrahydro-pyridine；4-(1-Benzothiophen-3-yl)-1,2,3,6-tetrahydropyridine
• CAS: 332387-44-7
• 化学式: C₁₃H₁₃NS
• 分子量: 215.319
• InChiKey: LPRHRRBXOMJSGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(benzothiophen-3-yl)-1,2,3,6-tetrahydropyridine 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 生成 4-苯并[b]噻吩-3-哌啶
  参考文献：
  名称：

  Piperidine derivatives as reuptake inhibitors

  摘要：

  本发明提供了式（I）的化合物以及一种抑制5-羟色胺再摄取和拮抗5-羟色胺受体的方法，包括向需要此类治疗的受试者施用式（I）的化合物的有效量。

  公开号：

  US06828332B1
• 作为产物：
  描述：

  3-溴苯并噻吩 在 正丁基锂 、 三氟乙酸 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.33h， 生成 4-(benzothiophen-3-yl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  一系列针对大鼠脑中多巴胺能和5-羟色胺能的1-丙基-4-芳基哌啶的系统体内筛选：支架跳跃方法。

  摘要：

  合成了一系列的1-丙基-4-芳基哌啶，并在体内和体外测试了它们对多巴胺能和5-羟色胺能系统的影响。在连接至哌啶环的五元和六元双环芳基环之间的支架跳跃对这些作用有显着影响。由3-吲哚，3-苯并异恶唑，3-苯并咪唑-2-酮和3-苯并噻吩生成有效的和选择性的多巴胺D 2受体拮抗剂。相反，3-苯并呋喃是单胺氧化酶（MAO）A的有效和选择性抑制剂。合成的化合物对3,4-二羟基苯基乙酸（DOPAC）水平的影响与其对多巴胺D 2的亲和力密切相关在4-芳基哌啶系列中，最有发展前景的化合物是6-氯-3-（1-丙基-4-哌啶基）-1 H-苯并咪唑-2-酮（19），在体内具有典型的多巴胺D 2受体拮抗剂特性，但仅部分降低了自发运动能力。这表明该化合物在患者中诱发帕金森氏症的倾向可能较低。

  DOI：

  10.1021/jm300975f

文献信息

• 1H-indole and benzo(b)thiophene derivatives with 4-(1,2,3,6-tetra:hydro:pyridinyl)- and 4-piperidinyl-groups bound to the heterocyclic ring as inhibitors of serotonin reuptake
  申请人：ELI LILLY AND COMPANY

  公开号：EP0812826A1

  公开（公告）日：1997-12-17

  The pharmaceutical use of novel compounds of formula I: where Z is a structure of formula A-B is -C=CH- or -C(R5)-CH2-; X is S or NR4; R1 is H, halo, formyl, C1-C4 alkyl, C1-C4 alkoxy, thienylmethyloxy, 4,5-dihydrothiazol-2-yl, cyano, nitro, carboxamido, trifluoromethyl or hydroxy; R2 is H or halo; R3 is H, C1-C4 alkyl, (C1-C4 alkylene)-aryl, or -CH2-Y-NR7R8; R4 is H, C1-C4 alkyl, C1-C5 acyl, or phenylsulfonyl; R5 is H or OH; R6 is H or methyl; Y is -CH2- or -C(O)-; R7 is pyridinyl; and R8 is H or -C(O)-(C3-C6 cycloalkyl); and pharmaceutically acceptable salts thereof.

  化合物的药用途：其中Z是formulaA-B结构，-C=CH-或-C(R5)-CH2-；X是S或NR4；R1是H、卤素、甲酰基、C1-C4烷基、C1-C4烷氧基、噻吩甲氧基、4,5-二氢噻唑-2-基、氰基、硝基、羧酰胺基、三氟甲基或羟基；R2是H或卤素；R3是H、C1-C4烷基、(C1-C4烷基)-芳基，或-CH2-Y-NR7R8；R4是H、C1-C4烷基、C1-C5酰基，或苯基磺酰基；R5是H或OH；R6是H或甲基；Y是-CH2-或-C(O)-；R7是吡啶基；R8是H或-C(O)-(C3-C6环烷基)；以及其药用上可接受的盐。
• [EN] ANTIDEPRESSANT PIPERIDINE DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXANS<br/>[FR] DERIVES PIPERIDINE D'HETEROCYCLE DE BENZODIOXANS FUSIONNES EN TANT QU'ANTIDEPRESSEURS
  申请人：WYETH CORP

  公开号：WO2004024733A1

  公开（公告）日：2004-03-25

  Compounds of the Formula: are useful for the treatment of depression (including but not limited to major depressive disorder, chi ldhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as premenstrual syndrome), attention deficit disorder (wit h and without hyperactivity), obsessive compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity, eating disorders such as anorexia nervosa and bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.

  该公式化合物用于治疗抑郁症（包括但不限于重性抑郁障碍、儿童抑郁和忧郁症）、焦虑、恐慌障碍、创伤后应激障碍、经前期失调性障碍（也称为经前综合征）、注意力缺陷障碍（有和无多动症）、强迫症、社交焦虑障碍、广泛性焦虑障碍、肥胖症、厌食症和暴食症、血管运动性潮红、可卡因和酒精成瘾、性功能障碍及相关疾病。
• Antidepressant piperidine derivatives of heterocycle-fused benzodioxans
  申请人：——

  公开号：US20040147523A1

  公开（公告）日：2004-07-29

  Compounds of the Formula: 1 are useful for the treatment of depression (including but not limited to major depressive disorder, childhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as premenstrual syndrome), attention deficit disorder (with and without hyperactivity), obsessive compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity, eating disorders such as anorexia nervosa and bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.

  式子为1的化合物对于治疗抑郁症（包括但不限于重度抑郁症、儿童抑郁症和慢性抑郁症）、焦虑症、恐慌症、创伤后应激障碍、经前期不良情绪障碍（也称经前综合征）、注意力缺陷障碍（有或无多动症）、强迫症、社交焦虑症、广泛性焦虑症、肥胖症、进食障碍（如厌食症和贪食症）、血管活性药物潮红、可卡因和酒精成瘾、性功能障碍及相关疾病具有治疗作用。
• Antidepressant piperidine derivatives of heterocyclefused benzodioxans
  申请人：Webb Byron Michael

  公开号：US20050228009A1

  公开（公告）日：2005-10-13

  Compounds of the Formula: are useful for the treatment of depression (including but not limited to major depressive disorder, childhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as pre-menstrual syndrome), attention deficit disorder (with and without hyperactivity), obsessive compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity, eating disorders such as anorexia nervosa and bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.

  公式为的化合物可用于治疗抑郁症（包括但不限于重度抑郁症、儿童抑郁症和慢性抑郁症）、焦虑、惊恐障碍、创伤后应激障碍、经前期不良情绪障碍（也称经前综合症）、注意力缺陷障碍（伴有或不伴有多动症）、强迫症、社交焦虑症、广泛性焦虑症、肥胖症、进食障碍如厌食症和贪食症、潮红、可卡因和酒精成瘾、性功能障碍及相关疾病。
• Antidepressant Piperidine Derivatives of Heterocycle-Fused Benzodioxans
  申请人：Webb Michael Byron

  公开号：US20090042895A1

  公开（公告）日：2009-02-12

  Compounds of the Formula: are useful for the treatment of depression (including but not limited to major depressive disorder, childhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as pre-menstrual syndrome), attention deficit disorder (with and without hyperactivity), obsessive compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity, eating disorders such as anorexia nervosa and bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.

  公式为：的化合物可用于治疗抑郁症（包括但不限于重度抑郁症、儿童抑郁症和心境恶劣）、焦虑症、恐慌症、创伤后应激障碍、经前期症候群（也称经前综合征）、注意力缺陷多动障碍（有和无过动症）、强迫症、社交焦虑症、广泛性焦虑症、肥胖症、饮食失调如厌食症和贪食症、潮红、可卡因和酒精成瘾、性功能障碍及相关疾病。