[1,1-biphenyl]-3-yl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate | 1417520-11-6

• 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: [1,1-biphenyl]-3-yl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate
• 英文别名: (3-Phenylphenyl) 1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate；(3-phenylphenyl) 1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxylate
• CAS: 1417520-11-6
• 化学式: C₂₄H₂₀N₂O₂
• 分子量: 368.435
• InChiKey: DSQDJFIPMKAAEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间羟基联苯 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 19.0h， 生成 [1,1-biphenyl]-3-yl 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate
  参考文献：
  名称：

  Tetrahydro-β-carboline derivatives targeting fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channels

  摘要：

  A series of twenty-five derivatives of tetrahydro-beta-carbolines 1-3 was synthesized and assayed on FAAH and TRPV1 and TRPA1 channels. Four carbamates, that is, 5a,c,e, and 9b inhibited FAAH with significant potency and interacted also effectively with TRPV1 and TRPA1 nociceptive receptors, while ureas 7b,d,f, and 8a,b were endowed with specific submicromolar TRPV1 modulating activities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.137

文献信息

• Novel dual-target FAAH and TRPV1 ligands as potential pharmacotherapeutics for pain management
  作者：Zhenrui Qiao、Shuyu Liu、Weibin zhai、Lei Jiang、Yunmeng Ma、Zhikang Zhang、Bingxin Wang、Jingwen Shao、Hai Qian、Fenqin Zhao、Lin Yan

  DOI：10.1016/j.ejmech.2024.116208

  日期：2024.3

  inhibition/antagonism in vitro, exerted powerful analgesic effects in formalin-induced pain test (phase II, in mice), desirable anti-inflammatory activity in carrageenan-induced paw edema in rats, no TRPV1-related hyperthermia side effect, and favorable pharmacokinetic properties. Meanwhile, the contributions of TRPV1 and FAAH to its antinociceptive effects were verified by target engagement and molecular docking

  同时抑制脂肪酸酰胺水解酶 （FAAH） 和拮抗瞬时受体电位香草酸 1 （TRPV1） 的双效药物是一种很有前途的更强的疼痛管理治疗方法，没有与单靶点药物相关的副作用。在这里，通过经典 TRPV1 拮抗剂和 FAAH 抑制剂的药效团之间的合理分子杂交，设计和合成了几个系列的双重 FAAH/TRPV1 阻滞剂。研究结果显示化合物 2r，在体外表现出很强的双重 FAAH/TRPV1 抑制/拮抗作用，在福尔马林诱导的疼痛试验 （II 期，小鼠） 中发挥强大的镇痛作用，在角叉菜胶诱导的大鼠足部水肿中具有理想的抗炎活性，无 TRPV1 相关的热疗副作用，以及良好的药代动力学特性。同时，TRPV1 和 FAAH 对其抗伤害作用的贡献通过靶点参与和分子对接研究得到验证。总体而言，化合物 2r 可以作为开发 FAAH/TRPV1 双激活配体以抵消疼痛的新支架。
• Tetrahydro-β-carboline derivatives targeting fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channels
  作者：Giorgio Ortar、Luciano De Petrocellis、Aniello Schiano Moriello、Marco Allarà、Enrico Morera、Marianna Nalli、Vincenzo Di Marzo

  DOI：10.1016/j.bmcl.2012.10.137

  日期：2013.1

  A series of twenty-five derivatives of tetrahydro-beta-carbolines 1-3 was synthesized and assayed on FAAH and TRPV1 and TRPA1 channels. Four carbamates, that is, 5a,c,e, and 9b inhibited FAAH with significant potency and interacted also effectively with TRPV1 and TRPA1 nociceptive receptors, while ureas 7b,d,f, and 8a,b were endowed with specific submicromolar TRPV1 modulating activities. (C) 2012 Elsevier Ltd. All rights reserved.