ethyl 1-ethyl-1,4-dihydro-7-(4-pyridinyl)-4-thioxo-3-quinolinecarboxylate | 164584-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 1-ethyl-1,4-dihydro-7-(4-pyridinyl)-4-thioxo-3-quinolinecarboxylate
• 英文别名: Ethyl 1-ethyl-7-pyridin-4-yl-4-sulfanylidenequinoline-3-carboxylate
• CAS: 164584-71-8
• 化学式: C₁₉H₁₈N₂O₂S
• 分子量: 338.43
• InChiKey: ORLLOWGMGLGZKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-ethyl-1,4-dihydro-7-(4-pyridinyl)-4-thioxo-3-quinolinecarboxylate 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 39.0h， 生成 ethyl 1-ethyl-1,4-dihydro-4-<<2-oxo-2-(phenylmethoxy)ethyl>imino>-7-(4-pyridinyl)-3-quinolinecarboxylate
  参考文献：
  名称：

  Cyclic Variations of 3-Quinolinecarboxamides and Effects on Antiherpetic Activity

  摘要：

  Supported by the antiherpetic properties of 3-quinolinecarboxamides and the importance of the planar intramolecular H-bonded beta-keto amide pharmacophore, a series of novel conformationally rigid analogues that contain a heterocyclic bridge between the 3- and 4-positions of the quinoline ring have been evaluated, Two isoxazolo-fused derivatives 17 and 23 displayed good in vitro antiherpetic potency that was similar to that of 1, the 3-quinolinecarboxamide that served as the comparison structure for this study. The pyrazolo, pyrrolo, and pyrimido derivatives showed considerably less or no activity. In vitro activity did not translate to in vivo efficacy. For 17, the lack of in vivo activity is likely a consequence of insufficient plasma drug levels (both C-max and duration) in mice relative to the MIC versus HSV-2.

  DOI：

  10.1021/jm00014a006
• 作为产物：
  描述：

  1-乙基-1,4-二氢-4-氧代-7-(4-吡啶基)喹啉-3-羧酸乙酯 在 吡啶 、 tetraphosphorus decasulfide 作用下， 反应 2.0h， 以77%的产率得到ethyl 1-ethyl-1,4-dihydro-7-(4-pyridinyl)-4-thioxo-3-quinolinecarboxylate
  参考文献：
  名称：

  Cyclic Variations of 3-Quinolinecarboxamides and Effects on Antiherpetic Activity

  摘要：

  Supported by the antiherpetic properties of 3-quinolinecarboxamides and the importance of the planar intramolecular H-bonded beta-keto amide pharmacophore, a series of novel conformationally rigid analogues that contain a heterocyclic bridge between the 3- and 4-positions of the quinoline ring have been evaluated, Two isoxazolo-fused derivatives 17 and 23 displayed good in vitro antiherpetic potency that was similar to that of 1, the 3-quinolinecarboxamide that served as the comparison structure for this study. The pyrazolo, pyrrolo, and pyrimido derivatives showed considerably less or no activity. In vitro activity did not translate to in vivo efficacy. For 17, the lack of in vivo activity is likely a consequence of insufficient plasma drug levels (both C-max and duration) in mice relative to the MIC versus HSV-2.

  DOI：

  10.1021/jm00014a006

文献信息

• Cyclic Variations of 3-Quinolinecarboxamides and Effects on Antiherpetic Activity
  作者：Mark P. Wentland、John A. Carlson、Peter H. Dorff、Suzanne C. Aldous、Robert B. Perni、Dorothy C. Young、Maureen G. Woods、Susan D. Kingsley、Kathryn A. Ryan、David Rosi、Marion L. Drozd、Frank J. Dutko

  DOI：10.1021/jm00014a006

  日期：1995.7

  Supported by the antiherpetic properties of 3-quinolinecarboxamides and the importance of the planar intramolecular H-bonded beta-keto amide pharmacophore, a series of novel conformationally rigid analogues that contain a heterocyclic bridge between the 3- and 4-positions of the quinoline ring have been evaluated, Two isoxazolo-fused derivatives 17 and 23 displayed good in vitro antiherpetic potency that was similar to that of 1, the 3-quinolinecarboxamide that served as the comparison structure for this study. The pyrazolo, pyrrolo, and pyrimido derivatives showed considerably less or no activity. In vitro activity did not translate to in vivo efficacy. For 17, the lack of in vivo activity is likely a consequence of insufficient plasma drug levels (both C-max and duration) in mice relative to the MIC versus HSV-2.