9-(2-哌啶乙基)-9H-咔唑 | 67196-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 9-(2-哌啶乙基)-9H-咔唑
• 英文名称: 9-(2-(piperidin-1-yl)ethyl)-9H-carbazole
• 英文别名: N-ethylpiperidine-9H-carbazole；9-(2-piperidino-ethyl)-carbazole；9-(2-Piperidino-aethyl)-carbazol；Carbazole, 9-(2-piperidinoethyl)-；9-(2-piperidin-1-ylethyl)carbazole
• CAS: 67196-16-1
• 化学式: C₁₉H₂₂N₂
• 分子量: 278.397
• InChiKey: VOHZHPQNDVLBCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(2-哌啶乙基)-9H-咔唑 在 ammonium acetate 、 三氯氧磷 作用下， 以 溶剂黄146 为溶剂， 反应 9.0h， 生成 N-ethylpiperidine-9H-carbazol-3-imidazo[4,5-f][1,10]phenantrolin
  参考文献：
  名称：

  Fang, Zhang Fang; Pei, Feng Wei; Chao, Zhang Jin, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 6, p. 713 - 717

  摘要：

  DOI：
• 作为产物：
  描述：

  咔唑 在 四丁基氟化铵 、 potassium carbonate 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 42.33h， 生成 9-(2-哌啶乙基)-9H-咔唑
  参考文献：
  名称：

  Rational Design and Synthesis of Thioridazine Analogues as Enhancers of the Antituberculosis Therapy

  摘要：

  Tuberculosis, caused by Mycobacterium tuberculosis, is still one of the leading infectious diseases globally. Therefore, novel approaches are needed to face this disease. Efflux pumps are known to contribute to the emergence of M tuberculosis drug resistance. Thioridazine has shown good anti-TB properties both in vitro and in vivo, likely due to its capacity to inhibit efflux mechanisms. Here we report the design and synthesis of a number of putative efflux inhibitors inspired by the structure of thioridazine. Compounds were evaluated for their in vitro and ex vivo activity against M. tuberculosis H37Rv. Compared to the parent molecule, some of the compounds synthesized showed higher efflux inhibitory capacity, less cytotoxicity, and a remarkable synergistic effect with anti-TB drugs both in vitro and in human macrophages, demonstrating their potential to be used as coadjuvants for the treatment of tuberculosis.

  DOI：

  10.1021/acs.jmedchem.5b00428

文献信息

• CARBAZOLE DERIVATIVES ACTING ON 5-HT7 RECEPTOR
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20160244408A1

  公开（公告）日：2016-08-25

  Disclosed are carbazole derivatives and pharmaceutically acceptable salts thereof that act on the 5-HT 7 receptor. The carbazole derivatives and the pharmaceutically acceptable salts thereof have high binding affinities for the 5-HT 7 serotonin receptor and antagonistic activities against the 5-HT 7 serotonin receptor. Further disclosed are pharmaceutical compositions including the compounds as active ingredients. The pharmaceutical compositions are useful as therapeutic and prophylactic agents for central nervous system diseases where antagonistic activities against 5-HT 7 are required, such as depression, migraine, anxiety, pain, inflammatory pain, neuropathic pain, body temperature dysregulation, circadian rhythm dysregulation, sleep disturbance, and smooth muscle-related diseases.

  揭示了对5-HT7受体起作用的咔唑衍生物及其药用盐。这些咔唑衍生物及其药用盐对5-HT7 5-羟色胺受体具有高结合亲和力，并具有对5-HT7 5-羟色胺受体的拮抗活性。此外，还披露了包括这些化合物作为活性成分的药物组合物。这些药物组合物可用作治疗和预防中枢神经系统疾病的药物，其中需要对5-HT7具有拮抗活性，如抑郁症、偏头痛、焦虑、疼痛、炎症性疼痛、神经痛、体温失调、昼夜节律失调、睡眠障碍和平滑肌相关疾病。
• Efficient and Regioselective Ruthenium-catalyzed Hydro-aminomethylation of Olefins
  作者：Lipeng Wu、Ivana Fleischer、Ralf Jackstell、Matthias Beller

  DOI：10.1021/ja312271c

  日期：2013.3.13

  An efficient and regioselective ruthenium-catalyzed hydroaminomethlyation of olefins is reported. Key to success is the use of specific 2-phosphino-substituted imidazole ligands and triruthenium dodecacarbonyl as catalyst. Both industrially important aliphatic as well as various functionalized olefins react with primary and secondary amines to give the corresponding secondary and tertiary amines generally in high yields (up to 96%) and excellent regioselectivities (n/iso up to 99:1).
• Pratesi; Castorina, Farmaco, Edizione Scientifica, 1954, vol. 9, p. 144,152
  作者：Pratesi、Castorina

  DOI：——

  日期：——
• US9663464B2
  申请人：——

  公开号：US9663464B2

  公开（公告）日：2017-05-30
• Rational Design and Synthesis of Thioridazine Analogues as Enhancers of the Antituberculosis Therapy
  作者：Marco Pieroni、Diana Machado、Elisa Azzali、Sofia Santos Costa、Isabel Couto、Gabriele Costantino、Miguel Viveiros

  DOI：10.1021/acs.jmedchem.5b00428

  日期：2015.8.13

  Tuberculosis, caused by Mycobacterium tuberculosis, is still one of the leading infectious diseases globally. Therefore, novel approaches are needed to face this disease. Efflux pumps are known to contribute to the emergence of M tuberculosis drug resistance. Thioridazine has shown good anti-TB properties both in vitro and in vivo, likely due to its capacity to inhibit efflux mechanisms. Here we report the design and synthesis of a number of putative efflux inhibitors inspired by the structure of thioridazine. Compounds were evaluated for their in vitro and ex vivo activity against M. tuberculosis H37Rv. Compared to the parent molecule, some of the compounds synthesized showed higher efflux inhibitory capacity, less cytotoxicity, and a remarkable synergistic effect with anti-TB drugs both in vitro and in human macrophages, demonstrating their potential to be used as coadjuvants for the treatment of tuberculosis.