N-(4-trifluoromethylphenyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-amide | 1417520-12-7

• 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: N-(4-trifluoromethylphenyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-amide
• 英文别名: N-(4-(trifluoromethyl)phenyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxamide；N-[4-(trifluoromethyl)phenyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxamide
• CAS: 1417520-12-7
• 化学式: C₁₉H₁₆F₃N₃O
• 分子量: 359.351
• InChiKey: ZIYQEALFXCILIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  48.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,2,3,4-四氢去甲哈尔满盐酸盐 、 4-三氟甲基苯基异氰酸酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 N-(4-trifluoromethylphenyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-amide
  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

• Study on chemical modification and analgesic activity of N-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl) piperazine-1-carboxamide
  作者：Cunbin Nie、Qifei Li、Yue Qiao、Jing Hu、Mengkang Gao、Yusui Wang、Zhenrui Qiao、Qiang Wang、Lin Yan、Hai Qian

  DOI：10.1016/j.ejmech.2020.112236

  日期：2020.5

  pharmacokinetic profile, therefore, it was not developed further. In order to enrich the structural types of urea-based TRPV1 antagonists, two series of novel analogs, in which the pyridine ring of BCTC was replaced with a mildly basic pyrimidine ring or 1,2,3,4-tetrahydro-β-carboline scaffold, were designed and synthesized. Advancing the structure-activity relationship of these two series led to the discovery of

  N-（4-叔丁基苯基）-4-（3-氯吡啶-2-基）哌嗪-1-羧酰胺（BCTC）是一种有效且经过广泛研究的基于尿素的TRPV1拮抗剂。尽管BCTC可以有效减轻大鼠的慢性疼痛，但它显示出明显的高热副作用和不理想的药代动力学特征，因此没有进一步发展。为了丰富基于尿素的TRPV1拮抗剂的结构类型，使用了两个新的类似物系列，其中BCTC的吡啶环被温和的碱性嘧啶环或1,2,3,4-四氢-β-咔啉骨架取代，进行了设计和合成。推进这两个系列的结构-活性关系导致发现N-（4-甲氧基苯基）-1,3,4,9-四氢-2 H-吡啶基[3,4- b] indole-2-carboxamide（7o），与先导化合物BCTC相比，具有改善的药理和耐受性。
• 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.