2H-pyrrolo[3,4-c]quinolin-4(5H)-one | 748159-52-6

• 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: 2H-pyrrolo[3,4-c]quinolin-4(5H)-one
• 英文别名: 2,5-Dihydropyrrolo[3,4-c]quinolin-4-one；2,5-dihydropyrrolo[3,4-c]quinolin-4-one
• CAS: 748159-52-6
• 化学式: C₁₁H₈N₂O
• 分子量: 184.197
• InChiKey: UVBQBXDMHXIBNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2H-pyrrolo[3,4-c]quinolin-4(5H)-one 在 palladium 10% on activated carbon 、 氢气 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 20.0~146.0 ℃ 、193.06 kPa 条件下， 反应 118.17h， 生成 4-[(1-piperid-4-yl)methyloxy]-2-methyl-2H-pyrrolo[3,4-c]quinoline
  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
• 作为产物：
  描述：

  ethyl (E)-3-(2-aminophenyl)acrylate 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 11.0h， 生成 2H-pyrrolo[3,4-c]quinolin-4(5H)-one
  参考文献：
  名称：

  One pot synthesis of pyrrolo[3,4-c]quinolinone/pyrrolo[3,4-c]quinoline derivatives from 2-aminoarylacrylates/2-aminochalcones and tosylmethyl isocyanide (TosMIC)

  摘要：

  据报道，在碱性条件下，2-氨基芳基丙烯酸酯/2-氨基查耳酮与对甲苯基甲基异氰酸酯（TosMIC）通过一锅范柳森反应和环化反应，可获得 2H-吡咯并[3,4-c]喹啉-4(5H)-酮/2H-吡咯并[3,4-c]喹啉衍生物，这是一种高效实用的合成方法。所需的产品可以中等到良好的收率获得。

  DOI：

  10.1039/c4ob01580k

文献信息

• [EN] COMPOUND WITH SEROTONINERGIC ACTIVITY, PROCESS FOR PREPARING IT AND PHARMACEUTICAL COMPOSITION COMPRISING IT<br/>[FR] COMPOSÉ PRÉSENTANT UNE ACTIVITÉ SÉROTONINERGIQUE, SON PROCÉDÉ DE FABRICATION ET COMPOSITION PHARMACEUTIQUE LA COMPRENANT
  申请人：ACRAF

  公开号：WO2010012611A1

  公开（公告）日：2010-02-04

  Compound of formula (I) in which R1, R2 and R3 are defined in the following description, and the pharmaceutically acceptable acid-addition or base-addition salts thereof. The invention also relates to a process and an intermediate for preparing it, and to a pharmaceutical composition comprising it. The invention also relates to the use of a novel 2H-pyrrolo[3,4-c]quinoline compound for preparing a pharmaceutical composition that is active in the treatment of disturbances of the serotoninergic system.

  化合物的化学式（I），其中R1、R2和R3在以下描述中定义，并其药学上可接受的酸加合物或碱加合物盐。本发明还涉及用于制备该化合物的过程和中间体，以及包含它的药物组合物。本发明还涉及使用一种新型2H-吡咯并[3,4-c]喹啉化合物制备对5-羟色胺系统紊乱治疗有效的药物组合物。
• COMPOUND WITH SEROTONINERGIC ACTIVITY, PROCESS FOR PREPARING IT AND PHARMACEUTICAL COMPOSITION COMPRISING IT
  申请人：Alisi Maria Alessandra

  公开号：US20110160201A1

  公开（公告）日：2011-06-30

  Compound of formula (I) in which R1, R2 and R3 are defined in the following description, and the pharmaceutically acceptable acid-addition or base-addition salts thereof. The invention also relates to a process and an intermediate for preparing it, and to a pharmaceutical composition comprising it. The invention also relates to the use of a novel 2H-pyrrolo[3,4-c]quinoline compound for preparing a pharmaceutical composition that is active in the treatment of disturbances of the serotoninergic system.

  公式（I）的复合物，其中R1、R2和R3的定义如下所述，并且其药学上可接受的酸加成物或碱加成物盐。本发明还涉及一种制备它的过程和中间体，以及包含它的制药组合物。本发明还涉及使用一种新的2H-吡咯并[3,4-c]喹啉化合物制备具有治疗5-羟色胺系统紊乱活性的制药组合物。
• [1,2,4]TRIAZOLO[4,3-a]QUINOXALINONE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：NOVO NORDISK A/S

  公开号：EP0781282A1

  公开（公告）日：1997-07-02
• [EN] [1,2,4]TRIAZOLO[4,3-a]QUINOXALINONE DERIVATIVES, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE LA [1,2,4]TRIAZOLO[4,3-A]QUINOXALINONE, LEUR PREPARATION ET UTILISATION
  申请人：NOVO NORDISK A/S

  公开号：WO1996008493A1

  公开（公告）日：1996-03-21

  (EN) [1,2,4]triazolo[4,3-a]quinoxalinone compounds of general formula (I) wherein R1 is POX'X' or alkyl substituted with COX' or POX'X', and X' and X' independently are hydroxy or alkoxy, and R6, R7, R8 and R9 independently are hydrogen; alkyl; halogen; NH2; NO2; CN; CF3 SO2NY'Y' or COZ' wherein Z' is NY'Y' or alkyl and Y' and Y' independently are hydrogen or alkyl; triazolyl; imidazolyl or imidazolyl substituted with phenyl or alkyl, are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.(FR) La présente invention concerne des composés [1,2,4]triazolo[4,3-a]quinoxalinone représentés par la formule générale (I) dans laquelle R1 est POX'X' ou alkyle à substitution COX' ou POX'X', X' et X' étant indépendamment hydroxy ou alcoxy, et R6, R7, R8 et R9 étant indépendamment hydrogène; alkyle; halogène; NH2; NO2; CN; CF3; SO2NY'Y' ou COZ', Z' représentant NY'Y' ou alkyle, et Y' et Y' représentant indépendamment hydrogène ou alkyle; triazolyle; imidazolyle, ou imidazolyle à substitution phényle ou alkyle. Ces composés sont utiles pour le traitement des symptômes provoqués par l'hyperactivité des neurotransmetteurs d'excitation.
• 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.