tert-butyl 4-(1-methylindole-2-carbonyl)piperazine-1-carboxylate | 1081119-73-4

• 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
• 英文名称: tert-butyl 4-(1-methylindole-2-carbonyl)piperazine-1-carboxylate
• 英文别名: tert-butyl 4-[(1-methylindol-2-yl)carbonyl]piperazinecarboxylate；tert-butyl 4-[(1-methyl-1H-indol-2-yl)carbonyl]piperazine-1-carboxylate
• CAS: 1081119-73-4
• 化学式: C₁₉H₂₅N₃O₃
• 分子量: 343.426
• InChiKey: PEXODIWJPZEVDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(1-methylindole-2-carbonyl)piperazine-1-carboxylate 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Dipeptidyl peptidase-4 inhibitor with β-amino amide scaffold: Synthesis, SAR and biological evaluation

  摘要：

  Inhibitors of dipeptidyl peptidase-4 (DPP4) have been shown to be effective treatments for type 2 diabetes. Several series of beta-amino amide containing piperazine derivatives have been prepared and evaluated as a inhibitor of DPP4. Finally compound 5m was selected for further evaluation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.019

文献信息

• EBI2 MODULATORS
  申请人：SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE

  公开号：US20160214951A1

  公开（公告）日：2016-07-28

  Provided herein are small molecule Epstein-Barr virus-induced G-protein coupled receptor 2 (EBI2) modulator compounds, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds. EBI2 is a therapeutic target for the treatment of a variety of diseases or conditions. In some embodiments, EBI2 is a therapeutic target for the treatment of diseases or conditions such as, but not limited to, autoimmune diseases or conditions, cancer, and cardiovascular disease.

  本文提供了小分子埃普斯坦-巴尔病毒诱导的G蛋白偶联受体2（EBI2）调节剂化合物，包括这些化合物的组合物，以及使用这些化合物和组合物的方法。EBI2是治疗多种疾病或病症的治疗靶点。在某些实施例中，EBI2是治疗自身免疫性疾病或病症、癌症和心血管疾病等疾病或病症的治疗靶点。
• Development of indole-2-carbonyl piperazine urea derivatives as selective FAAH inhibitors for efficient treatment of depression and pain
  作者：Yanguo Shang、Minghui Wang、Qingjing Hao、Tao Meng、Lili Li、Junwei Shi、Guoqing Yang、Zhilan Zhang、Kan Yang、Jinxin Wang

  DOI：10.1016/j.bioorg.2022.106031

  日期：2022.11

  Fatty acid amide hydrolase (FAAH), a serine hydrolase with significant role in the hydrolysis of endocannabinoids, is a promising therapeutic target for peripheral and central nervous system related disorders, including pain, neuroinflammation and depression. Employing a structure-based approach, a novel series of indole-2-carbonyl piperazine urea derivatives were designed and synthesized as FAAH inhibitors

  脂肪酸酰胺水解酶 (FAAH) 是一种 丝氨酸 水解酶，在内源性大麻素的水解中具有重要作用 ，是治疗周围和中枢神经系统相关疾病（包括疼痛、神经炎症和抑郁症）的有希望的治疗靶点。采用基于结构的方法，设计并合成了一系列新的吲哚-2-羰基哌嗪脲衍生物作为 FAAH 抑制剂，用于治疗疼痛抑郁症的合并症。其中，化合物4i成为最有效的抑制剂（IC 50 = 0.12 μM)，与 CES2、ABHD6、MAGL 和大麻素受体相比具有良好的选择性，在人肝微粒体中也表现出优异的代谢稳定性，在啮齿动物中也表现出足够的药代动力学特征。用4i治疗抑郁大鼠表现出良好的抗抑郁样作用，不仅通过增加海马中 BDNF 的水平，而且通过抑制海马神经元的凋亡。此外，4i在体外有效抑制 LPS 诱导的神经炎症。此外，4i表现出有效的镇痛活性，这表明其在疼痛和抑郁症的治疗应用中很有前景。这些有意义的结果揭示了 FAAH 抑制剂作为有前景的疼痛抑郁合并症治疗药物。
• US9776979B2
  申请人：——

  公开号：US9776979B2

  公开（公告）日：2017-10-03
• [EN] EBI2 MODULATORS<br/>[FR] MODULATEURS EBI2
  申请人：SANFORD BURNHAM MED RES INST

  公开号：WO2015048570A2

  公开（公告）日：2015-04-02

  Provided herein are small molecule Epstein-Barr virus-induced G-protein coupled receptor 2 (EBI2) modulator compounds, compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.
• Dipeptidyl peptidase-4 inhibitor with β-amino amide scaffold: Synthesis, SAR and biological evaluation
  作者：Heung Jae Kim、Woo Young Kwak、Jong Pil Min、Si Young Sung、Ha Dong Kim、Mi Kyung Kim、Hae Sun Kim、Kyung Jin Park、Moon Ho Son、Soon Hoe Kim、Bong Jin Lee

  DOI：10.1016/j.bmcl.2012.07.019

  日期：2012.9

  Inhibitors of dipeptidyl peptidase-4 (DPP4) have been shown to be effective treatments for type 2 diabetes. Several series of beta-amino amide containing piperazine derivatives have been prepared and evaluated as a inhibitor of DPP4. Finally compound 5m was selected for further evaluation. (C) 2012 Elsevier Ltd. All rights reserved.