6-methoxy-4-methyl-1-phenyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline | 113569-38-3

• 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: 6-methoxy-4-methyl-1-phenyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline
• 英文别名: 6-Methoxy-4-methyl-1-phenyl-2,3-dihydro-1H-pyrrolo[3,2-c]chinolin；methyl 4-methyl-1-phenyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-6-yl ether；6-methoxy-4-methyl-1-phenyl-2,3-dihydropyrrolo[3,2-c]quinoline
• CAS: 113569-38-3
• 化学式: C₁₉H₁₈N₂O
• 分子量: 290.365
• InChiKey: JOXFOVKOHKFZNG-UHFFFAOYSA-N

物化性质

• 熔点：
  151-151.5 °C
• 沸点：
  480.8±45.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-chloro-3-(2-chloro-ethyl)-8-methoxy-2-methyl-quinoline 、 aniline hydrochloride 以 正丁醇 为溶剂， 反应 22.0h， 以27%的产率得到6-methoxy-4-methyl-1-phenyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 1. 1-Aryl-4-methylpyrrolo[3,2-c]quinolines as conformationally restrained analogs of 4-(arylamino)quinolines

  摘要：

  The 4-(arylamino)quinoline 4, previously described as an antiulcer compound, is shown to be an inhibitor of the gastric (H+/K+)-ATPase. It is postulated that 1-arylpyrrolo[3,2-c]quinolines 6 act as conformationally restrained analogues of 4. A series of derivatives of 6 has been prepared and shown to be potent inhibitors of the target enzyme in vitro. Substitution in the ortho position of the aryl ring is important for activity. Unsaturation in the 5-membered ring makes little difference, but introduction of heteroatoms into the same ring markedly reduces activity. In more detailed kinetic experiments, 15c and 4 both show reversible, K(+)-competitive binding to the enzyme, with submicromolar Ki values. The compounds appear to act at the lumenal face of the enzyme and to require protonation for activity. Several compounds in the series are shown to be potent inhibitors of pentagastrin-stimulated acid secretion in the rat.

  DOI：

  10.1021/jm00164a010

文献信息

• TOPICAL FORMULATIONS
  申请人：BECK Petra Helga

  公开号：US20100093691A1

  公开（公告）日：2010-04-15

  There is provided topical pharmaceutical compositions comprising compounds of formula I wherein R 1 , R 2 , R 3 and X have meanings given in the description. These compositions can be used to treat microbial infections and to kill clinically latent microorganisms.

  提供了一种含有I式化合物的局部制药组合物，其中R1、R2、R3和X的含义在说明中给出。这些组合物可用于治疗微生物感染并杀死临床潜伏微生物。
• USE OF PYRROLOQUINOLINE COMPOUNDS TO KILL CLINICALLY LATENT MICROORGANISMS
  申请人：Beck Petra Helga

  公开号：US20120231995A1

  公开（公告）日：2012-09-13

  There is provided the use of compounds of formula I wherein R 1 , R 2 , R 3 and X have meanings given in the description, for the preparation of a medicament for killing clinically latent microorganisms. There is also provided the use of compounds of formula I for treating microbial infections, as well as certain compounds of formula I per se.

  提供了使用式子I中的化合物，其中R1、R2、R3和X的含义在说明中给出，用于制备杀死临床潜伏微生物的药物。还提供了使用式子I中的化合物治疗微生物感染的方法，以及某些式子I中的化合物本身。
• US8207187B2
  申请人：——

  公开号：US8207187B2

  公开（公告）日：2012-06-26
• US9694006B2
  申请人：——

  公开号：US9694006B2

  公开（公告）日：2017-07-04
• [EN] USE OF PYRROLOQUINOLINE COMPOUNDS TO KILL CLINICALLY LATENT MICROORGANISMS<br/>[FR] UTILISATION DE DÉRIVÉS DE PYRROLOQUINOLINE POUR L'ÉLIMINATION DE MICRO-ORGANISMES PERSISTANTS AU NIVEAU CLINIQUE
  申请人：HELPERBY THERAPEUTICS LTD

  公开号：WO2007054693A1

  公开（公告）日：2007-05-18

  [EN] There is provided the use of compounds of formula (I), wherein R¹ R² R³ and X have meanings given in the description, for the preparation of a medicament for killing clinically latent microorganisms. There is also provided the use of compounds of formula (I) for treating microbial infections, as well as certain compounds of formula (I) per se.
  [FR] La présente invention porte sur l'utilisation de composés de formule (I), où R¹ R² R³ et X ont les valeurs données dans la description, dans l'élaboration d'un médicament pour l'élimination de micro-organismes persistants au niveau clinique. La présente invention porte également sur l'utilisation des composés de formule (I) dans le traitement d'infections microbiennes, ainsi que sur certains composés de formule (I) en eux-mêmes.