ethyl (5,6-dihydro-2-methyl-4H-pyrrolo<3,2,1-ij>quinolin-1-yl)acetate | 148490-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl (5,6-dihydro-2-methyl-4H-pyrrolo<3,2,1-ij>quinolin-1-yl)acetate
• 英文别名: ethyl 5,6-dihydro-2-methyl-4H-pyrrolo[3,2,1-ij]quinoline-1-acetate；ethyl 2-(2-methyl-1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-3-yl)acetate
• CAS: 148490-36-2
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: ZMTBDZRQJRTWKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl (5,6-dihydro-2-methyl-4H-pyrrolo<3,2,1-ij>quinolin-1-yl)acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以90%的产率得到5,6-dihydro-1-(2-hydroxyethyl)-2-methyl-4H-pyrrolo<3,2,1-ij>quinoline
  参考文献：
  名称：

  Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of Pyrrolo[3,2,1-ij]quinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhibitory Properties. Potential Therapeutic Application in Asthma

  摘要：

  A series of pyrrolo[3,2,1-ij]quinoline derivatives was synthesized and evaluated for their in vitro and in vivo activities against histamine, platelet activating factor (PAF), and leukotrienes which are recognized to be of importance in asthma. The structure-activity relationship studies have shown that the optimum moiety on the 1-position of the pyrroloquinoline nucleus is a 2-[4-(4-methyl-2-pyridinyl)-1-piperazinyl]ethyl chain in conjunction with a methyl group on the 2-position for potent antagonism of both histamine and PAF. The introduction of substituents on the 8- and 4-positions was also investigated in order to increase the potency of 5-lipoxygenase inhibition while retaining or improving the activities against histamine and PAF. This series is exemplified by 4-n-butyl-5,6-dihydro-8-hydroxy-2-methyl-1-[2-[4-(4-methyl- 2-pyridinyl)-1-piperazinyl]ethyl]-4H-pyrrolo[3,2,1-ij]quinoline (24, KC 11404) which was found to be active against all three of the selected mediators. Compound 24 was found to be orally active in guinea pig models against the histaminic phase of antigen-induced bronchospasm and PAF-induced bronchoconstriction (ED(50) = 1.9 and 2.1 mu mol/kg, respectively). When tested against the leukotriene-dependent phase of the antigen-induced bronchoconstriction, compound 24 showed the same potency as zileuton.

  DOI：

  10.1021/jm00004a013
• 作为产物：
  描述：

  1-氨基-1,2,3,4-四氢喹啉 、 乙酰丙酸乙酯 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以40%的产率得到ethyl (5,6-dihydro-2-methyl-4H-pyrrolo<3,2,1-ij>quinolin-1-yl)acetate
  参考文献：
  名称：

  Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of Pyrrolo[3,2,1-ij]quinoline Derivatives: Potent Histamine and Platelet Activating Factor Antagonism and 5-Lipoxygenase Inhibitory Properties. Potential Therapeutic Application in Asthma

  摘要：

  A series of pyrrolo[3,2,1-ij]quinoline derivatives was synthesized and evaluated for their in vitro and in vivo activities against histamine, platelet activating factor (PAF), and leukotrienes which are recognized to be of importance in asthma. The structure-activity relationship studies have shown that the optimum moiety on the 1-position of the pyrroloquinoline nucleus is a 2-[4-(4-methyl-2-pyridinyl)-1-piperazinyl]ethyl chain in conjunction with a methyl group on the 2-position for potent antagonism of both histamine and PAF. The introduction of substituents on the 8- and 4-positions was also investigated in order to increase the potency of 5-lipoxygenase inhibition while retaining or improving the activities against histamine and PAF. This series is exemplified by 4-n-butyl-5,6-dihydro-8-hydroxy-2-methyl-1-[2-[4-(4-methyl- 2-pyridinyl)-1-piperazinyl]ethyl]-4H-pyrrolo[3,2,1-ij]quinoline (24, KC 11404) which was found to be active against all three of the selected mediators. Compound 24 was found to be orally active in guinea pig models against the histaminic phase of antigen-induced bronchospasm and PAF-induced bronchoconstriction (ED(50) = 1.9 and 2.1 mu mol/kg, respectively). When tested against the leukotriene-dependent phase of the antigen-induced bronchoconstriction, compound 24 showed the same potency as zileuton.

  DOI：

  10.1021/jm00004a013

文献信息

• 7-fused 2-(piperazinoalkyl) indole derivatives, intermediates and
  申请人：Kali-Chemie Pharma GmbH

  公开号：US05324725A1

  公开（公告）日：1994-06-28

  Pharmacologically active compounds having anti-allergic properties corresponding to the formula I ##STR1## which can be mono- or disubstituted in the phenyl ring and their acid addition salts and/or S-mono- or dioxides of sulfur-containing compounds of the formula I are described, together with processes and intermediates for their preparation.

  具有抗过敏性能的药理活性化合物对应于公式I ##STR1##，该化合物可以在苯环中单取代或双取代，并描述了它们的酸盐和/或含有硫的化合物的S-单取代物或二氧化物，以及用于它们制备的过程和中间体。
• US5324725A
  申请人：——

  公开号：US5324725A

  公开（公告）日：1994-06-28