4-[7-(trifluoromethyl)spiro[5H-pyrrolo[1,2-a]quinoxaline-4,4'-piperidine]-1'-carbonyl]benzonitrile | 1259379-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-[7-(trifluoromethyl)spiro[5H-pyrrolo[1,2-a]quinoxaline-4,4'-piperidine]-1'-carbonyl]benzonitrile
• CAS: 1259379-37-7
• 化学式: C₂₄H₁₉F₃N₄O
• 分子量: 436.436
• InChiKey: IFZNYDPKBDZQOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氨基-3-硝基三氟甲苯 在 4-二甲氨基吡啶 、 bismuth(III) chloride 、 sodium tetrahydroborate 、 N-羟基-7-氮杂苯并三氮唑 、 溶剂黄146 、 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 、 顺丁烯二酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-[7-(trifluoromethyl)spiro[5H-pyrrolo[1,2-a]quinoxaline-4,4'-piperidine]-1'-carbonyl]benzonitrile
  参考文献：
  名称：

  Discovery of pyrrolo-benzo-1,4-diazines as potent Nav1.7 sodium channel blockers

  摘要：

  A series of pyrrolo-benzo-1,4-diazine analogs have been synthesized and displayed potent Nav1.7 inhibitory activity and moderate selectivity over Nav1.5. The syntheses, structure-activity relationships, and selected pharmacokinetic data of these analogs are described. Compound 41 displayed anti-nociceptive efficacy in the rat CFA pain model at 100 mpk oral dosing.

  DOI：

  10.1016/j.bmcl.2014.07.060

文献信息

• [EN] METHODS FOR USING PYRROLO-BENZO-1,4-DIAZINES AS SODIUM CHANNEL BLOCKERS<br/>[FR] PROCÉDÉS D'UTILISATION DE PYRROLO-BENZO-1,4-DIAZINES EN TANT QUE BLOQUEURS DE CANAUX SODIQUES
  申请人：SCHERING CORP

  公开号：WO2010151597A1

  公开（公告）日：2010-12-29

  Pyrrolo-benzo-1,4-diazine compounds represented by Formula I or II, or pharmaceutically acceptable salts thereof, are blockers of voltage-gated sodium channels. Pharmaceutical compositions comprise an effective amount of the instant compounds, either alone, or in combination with one or more other therapeutically active compounds, and a pharmaceutically acceptable carrier. Methods of treating conditions associated with, or caused by, voltage-gated sodium channel activity, including, for example, acute pain, chronic pain, visceral pain, inflammatory pain, neuropathic pain, epilepsy or epilepsy conditions, irritable bowel syndrome, depression, anxiety, bipolar disorder, neurodegenerative disorders, psychiatric disorders, myotonia, arrhythmia, movement disorders, neuroendocrine disorders, ataxia, multiple sclerosis, irritable bowel syndrome, incontinence, neuropathy and tinnitus, comprise administering an effective amount of the present compounds, either alone, or in combination with one or more other therapeutically active compounds.
• Discovery of pyrrolo-benzo-1,4-diazines as potent Nav1.7 sodium channel blockers
  作者：Ginny D. Ho、Deen Tulshian、Ana Bercovici、Zheng Tan、Jennifer Hanisak、Stephanie Brumfield、Julius Matasi、Charles R. Heap、William G. Earley、Brandy Courneya、R. Jason Herr、Xiaoping Zhou、Terry Bridal、Diane Rindgen、Steve Sorota、Shu-Wei Yang

  DOI：10.1016/j.bmcl.2014.07.060

  日期：2014.9

  A series of pyrrolo-benzo-1,4-diazine analogs have been synthesized and displayed potent Nav1.7 inhibitory activity and moderate selectivity over Nav1.5. The syntheses, structure-activity relationships, and selected pharmacokinetic data of these analogs are described. Compound 41 displayed anti-nociceptive efficacy in the rat CFA pain model at 100 mpk oral dosing.