4-<(2-methylphenyl)amino>-3-nitroquinoline | 123438-64-2

• 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: 4-<(2-methylphenyl)amino>-3-nitroquinoline
• 英文别名: 4-(2-Methylphenylamino)-3-nitroquinoline；N-(2-methylphenyl)-3-nitroquinolin-4-amine
• CAS: 123438-64-2
• 化学式: C₁₆H₁₃N₃O₂
• 分子量: 279.298
• InChiKey: QUGFEESJCGYZSU-UHFFFAOYSA-N

物化性质

• 沸点：
  420.2±40.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-<(2-methylphenyl)amino>-3-nitroquinoline 在 tin(ll) chloride 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 1-o-Tolyl-1H-imidazo[4,5-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
• 作为产物：
  描述：

  4-氯-3-硝基喹啉 、 邻甲苯胺 在 盐酸 、 氯仿 、 碳酸氢钠 、 水 、 乙醇 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以to give the title compound (1.2 g, 43%) as orange needles, m.p. 137°-138°的产率得到4-<(2-methylphenyl)amino>-3-nitroquinoline
  参考文献：
  名称：

  Substituted quinoline derivatives

  摘要：

  本文描述了取代喹啉衍生物，特别是化合物1-(2-甲基苯基)咪唑[4,5-c]喹啉盐酸盐，作为抑制骨吸收的抑制剂。

  公开号：

  US05420135A1

文献信息

• Substituted quinoline derivatives
  申请人：Smith Kline & French Laboratories Limited

  公开号：US05420135A1

  公开（公告）日：1995-05-30

  Substituted quinoline derivatives are described as inhibitors bone resorption with in particular, the compound 1-(2-methylphenyl)imidazo[4,5-c]quinoline hydrochloride.

  本文描述了取代喹啉衍生物，特别是化合物1-(2-甲基苯基)咪唑[4,5-c]喹啉盐酸盐，作为抑制骨吸收的抑制剂。
• Support for fragrance samples
  申请人：MINNESOTA MINING AND MANUFACTURING COMPANY

  公开号：EP0441034A2

  公开（公告）日：1991-08-14

  Compounds of structure (I): in which R1 to R4 are the same or different and are each hydrogen, C1-4alkyl, C1-6alkoxy, phenyl, C1-6alkylthio, C1-4alkanoyl, amino, C1-6alkylamino, diC1-6alkylamino, halogen, trifluoromethyl or nitro, provided that at least two of R1 to R4 are hydrogen. R5 to R9 are the same or different and are each hydrogen, C1-6alkyl, C1-6alkoxy, C1-6alkylthio, halogen, cyano, amino, hydroxy, carbamoyl, carboxy, C1-6alkanoyl, trifluoromethyl or nitro, provided that at least two of R5 to R9 are hydrogen ; R10 is hydrogen, C1-6alkyl, C1-6alkoxy, halogen, hydroxy, -CH20H, C1-6alkylthio, NH(CH2)nOH in which n is 0 to 4 or a group -NR11R12 in which R11 and R12 are the same or different and are each hydrogen or C1-6alkyl or together with the nitrogen atom to which they are attached form a saturated or unsaturated ring ; and A is -N=N-; or -CH=N-; and pharmaceutically acceptable salts thereof, processes for their preparation, pharmaceutical compositions containing them and their use in therapy as inhibitors of gastric acid secretion and bone resorption.

  结构(I)的化合物： 其中 R1 至 R4 相同或不同，各自为氢、C1-4烷基、C1-6烷氧基、苯基、C1-6烷硫基、C1-4烷酰基、氨基、C1-6烷基氨基、二C1-6烷基氨基、卤素、三氟甲基或硝基，条件是 R1 至 R4 中至少有两个为氢。 R5 至 R9 相同或不同，各自为氢、C1-6烷基、C1-6烷氧基、C1-6烷硫基、卤素、氰基、氨基、羟基、氨基甲酰基、羧基、C1-6烷酰基、三氟甲基或硝基，条件是 R5 至 R9 中至少有两个是氢； R10 是氢、C1-6烷基、C1-6烷氧基、卤素、羟基、-CH20H、C1-6烷硫基、NH(CH2)nOH（其中 n 为 0 至 4）或基团-NR11R12（其中 R11 和 R12 相同或不同，且各自为氢或 C1-6 烷基，或与所连接的氮原子一起形成饱和或不饱和环）；以及 A 是-N=N-； 或-CH=N-； 及其药学上可接受的盐、制备工艺、含有它们的药物组合物，以及它们作为胃酸分泌抑制剂和骨吸收抑制剂在治疗中的用途。
• US5420135A
  申请人：——

  公开号：US5420135A

  公开（公告）日：1995-05-30
• 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
  作者：Thomas H. Brown、Robert J. Ife、David J. Keeling、Shiona M. Laing、Colin A. Leach、Michael E. Parsons、Carolyn A. Price、David R. Reavill、Kenneth J. Wiggall

  DOI：10.1021/jm00164a010

  日期：1990.2

  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.