1-isopropyl-N-[[1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl]methyl]-1H-indazole-3-carboxamide | 796847-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-isopropyl-N-[[1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl]methyl]-1H-indazole-3-carboxamide
• 英文别名: N-[[1-[2-(4-nitrophenyl)ethyl]piperidin-4-yl]methyl]-1-propan-2-ylindazole-3-carboxamide
• CAS: 796847-67-1
• 化学式: C₂₅H₃₁N₅O₃
• 分子量: 449.553
• InChiKey: FWCCAIJRQHYBFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-isopropyl-N-[[1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl]methyl]-1H-indazole-3-carboxamide 在 palladium 10% on activated carbon 盐酸 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 N((1-(2-(4-aminophenyl)ethyl)-4-piperidinyl)methyl)-1-(1-methylethyl)-1H-indazole-3-carboxamide dihydrochloride
  参考文献：
  名称：

  [EN] INDAZOLE HAVING ANALGESIC ACTIVITY ,
  [FR] INDAZOLES POSSEDANT UNE ACTIVITE ANALGESIQUE

  摘要：

  一种具有镇痛活性的吲唑衍生物，其制备方法以及含有该吲唑衍生物的药物组合物；该吲唑衍生物具有以下一般式：其中，X、Ra、Rb、Rc和Rd的含义如描述所述。

  公开号：

  WO2004101548A1
• 作为产物：
  描述：

  1-苄基哌啶-4-甲胺 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 溶剂黄146 、 甲苯 为溶剂， 20.0 ℃ 、241.32 kPa 条件下， 反应 38.0h， 生成 1-isopropyl-N-[[1-[2-(4-nitrophenyl)ethyl]-4-piperidinyl]methyl]-1H-indazole-3-carboxamide
  参考文献：
  名称：

  Discovery and Pharmacological Profile of New 1H-Indazole-3-carboxamide and 2H-Pyrrolo[3,4-c]quinoline Derivatives as Selective Serotonin 4 Receptor Ligands

  摘要：

  Since the discovery of the serotonin 4 receptor (5-HT4R), a large number of receptor ligands have been studied. The safety concerns and the lack of market success of these ligands have mainly been attributed to their lack of selectivity. In this study we describe the discovery of N-[(4- piperidinyl)methyl]-1H-indazole-3-carboxamide and 4-[(4-piperidinyl)methoxy]-2H-pyrrolo[3,4-c]quinoline derivatives as new 5-HT4R ligands endowed with high selectivity over the serotonin 2A receptor and human ether-a-go-go-related gene potassium ion channel. Within these series, two molecules (11ab and 12g) were identified as potent and selective 5-HT4R antagonists with good in vitro pharmacokinetic properties. These compounds were evaluated for their antinociceptive action in two analgesia animal models. 12g showed a significant antinociceptive effect in both models and is proposed as an interesting lead compound as a 5-HT4R antagonist with analgesic action.

  DOI：

  10.1021/jm300573d

文献信息

• Indazole having analgesic activity
  申请人：Alisi Alessandra Maria

  公开号：US20070010555A1

  公开（公告）日：2007-01-11

  An indazole having analgesic activity, a method for the preparation thereof and a pharmaceutical composition containing the same; the indazole has the following general formula: where X, R a , R b , R c and R d have the meanings stated in the description.

  一种具有镇痛活性的吲唑化合物，其制备方法和含有该化合物的制药组合物；该吲唑化合物具有以下一般式：其中X，Ra，Rb，Rc和Rd的含义在说明中给出。
• EP1622892A1
  申请人：——

  公开号：EP1622892A1

  公开（公告）日：2006-02-08
• INDAZOLES HAVING ANALGESIC ACTIVITY
  申请人：Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A.

  公开号：EP1622892B1

  公开（公告）日：2011-03-09
• US7662836B2
  申请人：——

  公开号：US7662836B2

  公开（公告）日：2010-02-16
• Discovery and Pharmacological Profile of New 1<i>H</i>-Indazole-3-carboxamide and 2<i>H</i>-Pyrrolo[3,4-<i>c</i>]quinoline Derivatives as Selective Serotonin 4 Receptor Ligands
  作者：Guido Furlotti、Maria Alessandra Alisi、Claudia Apicella、Alessandra Capezzone de Joannon、Nicola Cazzolla、Roberta Costi、Giuliana Cuzzucoli Crucitti、Beatrice Garrone、Alberto Iacovo、Gabriele Magarò、Giorgina Mangano、Gaetano Miele、Rosella Ombrato、Luca Pescatori、Lorenzo Polenzani、Federica Rosi、Marco Vitiello、Roberto Di Santo

  DOI：10.1021/jm300573d

  日期：2012.11.26

  Since the discovery of the serotonin 4 receptor (5-HT4R), a large number of receptor ligands have been studied. The safety concerns and the lack of market success of these ligands have mainly been attributed to their lack of selectivity. In this study we describe the discovery of N-[(4- piperidinyl)methyl]-1H-indazole-3-carboxamide and 4-[(4-piperidinyl)methoxy]-2H-pyrrolo[3,4-c]quinoline derivatives as new 5-HT4R ligands endowed with high selectivity over the serotonin 2A receptor and human ether-a-go-go-related gene potassium ion channel. Within these series, two molecules (11ab and 12g) were identified as potent and selective 5-HT4R antagonists with good in vitro pharmacokinetic properties. These compounds were evaluated for their antinociceptive action in two analgesia animal models. 12g showed a significant antinociceptive effect in both models and is proposed as an interesting lead compound as a 5-HT4R antagonist with analgesic action.