5-pentyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-pentyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one
• 英文别名: 5-pentyl-2H-pyrazolo[4,3-c]quinolin-3-one
• 化学式: C₁₅H₁₇N₃O
• 分子量: 255.319
• InChiKey: DEHBFUILWRDWEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-溴戊烷 、 5-pentyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以77%的产率得到2,5-dipentyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one
  参考文献：
  名称：

  Conformational Restriction Leading to a Selective CB₂ Cannabinoid Receptor Agonist Orally Active Against Colitis

  摘要：

  The CB2 cannabinoid receptor has been implicated in the regulation of intestinal inflammation. Following on from the promising activity of a series of 4-oxo-1,4-dihydroquinoline-3-carboxamide, we developed constrained analogues based on a 2H-pyrazolo[4,3-c]quinolin-3(5H)-one scaffold, with improved affinity for the hCB2 receptor and had very high selectivity over the hCB1 receptor. Importantly, the lead of this series (26, hCB2: K i = 0.39 nM, hCB1: K i > 3000 nM) was found to protect mice against experimental colitis after oral administration.

  DOI：

  10.1021/ml500439x
• 作为产物：
  描述：

  2-苯基氨基亚甲基-丙二酸二乙酯 在 tetraphosphorus decasulfide 、 二苯醚 、 sodium hydride 、 一水合肼 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 5-pentyl-2H-pyrazolo[4,3-c]quinolin-3(5H)-one
  参考文献：
  名称：

  Conformational Restriction Leading to a Selective CB₂ Cannabinoid Receptor Agonist Orally Active Against Colitis

  摘要：

  The CB2 cannabinoid receptor has been implicated in the regulation of intestinal inflammation. Following on from the promising activity of a series of 4-oxo-1,4-dihydroquinoline-3-carboxamide, we developed constrained analogues based on a 2H-pyrazolo[4,3-c]quinolin-3(5H)-one scaffold, with improved affinity for the hCB2 receptor and had very high selectivity over the hCB1 receptor. Importantly, the lead of this series (26, hCB2: K i = 0.39 nM, hCB1: K i > 3000 nM) was found to protect mice against experimental colitis after oral administration.

  DOI：

  10.1021/ml500439x

文献信息

• DERIVATIVES OF 2H-PYRAZOLO[4,3-C]QUINOLIN-3(5H)-ONE AND USE THEREOF
  申请人：UNIVERSITE DU DROIT ET DE LA SANTE LILLE 2

  公开号：US20170137419A1

  公开（公告）日：2017-05-18

  The invention relates to compounds of formula (I) or the pharmaceutically acceptable solvates thereof, as well as to the use thereof as a drug.

  本发明涉及式(I)化合物或其药学上可接受的溶剂化物，以及其作为药物的用途。
• DÉRIVÉS DE 2H-PYRAZOLO [ 4,3-C ] QUINOLIN-3-ONE ET SON UTILISATION (5H)
  申请人：Université du Droit et de la Santé de Lille 2

  公开号：EP3154981A1

  公开（公告）日：2017-04-19
• [EN] DERIVATIVES OF 2H-PYRAZOLO[4,3-C]QUINOLIN-3(5H)-ONE AND USE THEREOF<br/>[FR] DERIVES DE 2H-PYRAZOLO[4,3-C]QUINOLIN-3(5H)-ONE ET LEUR UTILISATION
  申请人：UNIV LILLE II DROIT & SANTE

  公开号：WO2015189523A1

  公开（公告）日：2015-12-17

  L'invention concerne des composés de Formule (I) ou leurs solvates pharmaceutiquement acceptables, ainsi que leur utilisation en tant que médicament.
• Conformational Restriction Leading to a Selective CB₂ Cannabinoid Receptor Agonist Orally Active Against Colitis
  作者：Jamal El Bakali、Giulio G. Muccioli、Mathilde Body-Malapel、Madjid Djouina、Frédérique Klupsch、Alina Ghinet、Amélie Barczyk、Nicolas Renault、Philippe Chavatte、Pierre Desreumaux、Didier M. Lambert、Régis Millet

  DOI：10.1021/ml500439x

  日期：2015.2.12

  The CB2 cannabinoid receptor has been implicated in the regulation of intestinal inflammation. Following on from the promising activity of a series of 4-oxo-1,4-dihydroquinoline-3-carboxamide, we developed constrained analogues based on a 2H-pyrazolo[4,3-c]quinolin-3(5H)-one scaffold, with improved affinity for the hCB2 receptor and had very high selectivity over the hCB1 receptor. Importantly, the lead of this series (26, hCB2: K i = 0.39 nM, hCB1: K i > 3000 nM) was found to protect mice against experimental colitis after oral administration.