4-Oxo-1,4-dihydro-quinoline-3,6-dicarboxylic acid 3-ethyl ester

• 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-Oxo-1,4-dihydro-quinoline-3,6-dicarboxylic acid 3-ethyl ester
• 英文别名: 3-ethoxycarbonyl-4-oxo-1H-quinoline-6-carboxylic acid
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: VDKMFRGWRQALMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-氯苯胺 、 4-Oxo-1,4-dihydro-quinoline-3,6-dicarboxylic acid 3-ethyl ester 以 二苯醚 为溶剂， 生成 3-(3-Chloro-phenylcarbamoyl)-4-hydroxy-quinoline-6-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator

  摘要：

  A series of novel quinoline-3-carboxamide derivatives were synthesized and evaluated for their immunomodulatory activity. The compounds were tested in vitro for effects on spleen lymphocyte proliferation and TNF-alpha production by macrophage. Three compounds showed immunomodulatory profiles similar to and more potent than those of linomide and FR137316 and were selected for further pharmacological studies in vivo. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.040
• 作为产物：
  描述：

  2-[(4-carboxy-phenylamino)-methylene]-malonic acid diethyl ester 以 二苯醚 为溶剂， 生成 4-Oxo-1,4-dihydro-quinoline-3,6-dicarboxylic acid 3-ethyl ester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator

  摘要：

  A series of novel quinoline-3-carboxamide derivatives were synthesized and evaluated for their immunomodulatory activity. The compounds were tested in vitro for effects on spleen lymphocyte proliferation and TNF-alpha production by macrophage. Three compounds showed immunomodulatory profiles similar to and more potent than those of linomide and FR137316 and were selected for further pharmacological studies in vivo. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.040

文献信息

• Solid phase synthesis of quinolones
  作者：Sanjay K. Srivastava、W. Haq、P.K. Murthy、P.M.S. Chauhan

  DOI：10.1016/s0960-894x(99)00326-1

  日期：1999.7

  Solid phase syntheses of ethyl 6-carboxyquinol-4(1H)-one-3-carboxylate (5) and N-substituted 6-carboxyquinol-4(IH)-one-3-carboxamides 7a-d have been described Antifilarial in vitro activities of 5,7a-d against Brugia malayi have also been delineated. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator
  作者：Jun-Feng He、Liu-Hong Yun、Ri-Fang Yang、Zhi-Yong Xiao、Jun-Ping Cheng、Wen-Xia Zhou、Yong-Xiang Zhang

  DOI：10.1016/j.bmcl.2005.04.040

  日期：2005.6

  A series of novel quinoline-3-carboxamide derivatives were synthesized and evaluated for their immunomodulatory activity. The compounds were tested in vitro for effects on spleen lymphocyte proliferation and TNF-alpha production by macrophage. Three compounds showed immunomodulatory profiles similar to and more potent than those of linomide and FR137316 and were selected for further pharmacological studies in vivo. (c) 2005 Elsevier Ltd. All rights reserved.