3-ethyl-2-oxo-1,2-dihydro-4-quinolinecarboxylic acid | 64880-80-4

• 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: 3-ethyl-2-oxo-1,2-dihydro-4-quinolinecarboxylic acid
• 英文别名: 3-ethyl-2-oxo-1,2-dihydro-quinoline-4-carboxylic acid；3-Ethyl-2-oxo-1,2-dihydro-4-chinolincarbonsaeure；4-Carboxy-3-ethyl-2-oxo-1,2-dihydro-chinolin；3-Ethyl-4-carboxy-2-chinolon；3-ethyl-2-oxo-1H-quinoline-4-carboxylic acid
• CAS: 64880-80-4
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: RDABDYFOWPWVIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethyl-2-oxo-1,2-dihydro-4-quinolinecarboxylic acid 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-氯-N,N,3-三乙基喹啉-4-甲酰胺
  参考文献：
  名称：

  Further Studies on the Interaction of the 5-Hydroxytryptamine₃ (5-HT₃) Receptor with Arylpiperazine Ligands. Development of a New 5-HT₃ Receptor Ligand Showing Potent Acetylcholinesterase Inhibitory Properties

  摘要：

  Novel arylpiperazine derivatives bearing lipophilic probes were designed, synthesized, and evaluated for their potential ability to interact with the 5-hydroxytryptamine(3) (5-HT3) receptor. Most of the new compounds show subnanomolar 5-HT3 receptor affinity. Ester 6bc showing a picomolar K-i value is one of the most potent 5-HT3 receptor ligands so far synthesized. The structure-affinity relationship study suggests the existence of a certain degree of conformational freedom of the amino acid residues interacting with the substituents in positions 3 and 4 of the quipazine quinoline nucleus. Thus, the tacrine-related heterobivalent ligand 6o was designed in an attempt to capitalize on the evidence of such a steric tolerance. Compound 6o shows a nanomolar potency for both the 5-HT3 receptor and the human AChE and represents the first example of a rationally designed high-affinity 5-HT3 receptor ligand showing nanomolar AChE inhibitory activity. Finally, the computational analysis performed on compound 6o allowed the rationalization of the structure-energy determinants for AChE versus BuChE selectivity and revealed the existence of a subsite at the boundary of the 5-HT3 receptor extracellular domain, which could represent a "peripheral" site similar to that evidenced in the AChE gorge.

  DOI：

  10.1021/jm0493461
• 作为产物：
  描述：

  4-Carboxy-3-vinyl-2-quinolone 以65%的产率得到
  参考文献：
  名称：

  RAMASAMY K.; KALYANASUNDARAM S. K.; SHANMUGAM P., SYNTHESIS, 1978, NO 7, 545-547

  摘要：

  DOI：

文献信息

• Certain 2-oxo-quinoline carboxylates or corresponding carboxamides
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05248684A1

  公开（公告）日：1993-09-28

  There is disclosed a heterocyclic compound represented by general formula: ##STR1## wherein R.sup.1 represents hydrogen, lower alkyl or aryl; R.sup.2 represents hydrogen, hydroxyl or lower alkyl; A represents CH or N; X represents --O-- or --NH--; R.sup.3 represents hydrogen, hydroxyl or lower alkyl; R.sup.4 represents lower alkyl; represents 0 or 1, or a pharmaceutically acceptable salt thereof.

  公开了一种由通式表示的杂环化合物：##STR1##其中R.sup.1代表氢、较低的烷基或芳基；R.sup.2代表氢、羟基或较低的烷基；A代表CH或N；X代表--O--或--NH--；R.sup.3代表氢、羟基或较低的烷基；R.sup.4代表较低的烷基；代表0或1，或其药学上可接受的盐。
• 5-HT3 receptor antagonists. 1. New quinoline derivatives
  作者：Hiroaki Hayashi、Yoshikazu Miwa、Ichiro Miki、Shunji Ichikawa、Nobuyuki Yoda、Akio Ishii、Motomichi Kono、Fumio Suzuki

  DOI：10.1021/jm00104a016

  日期：1992.12

  not observed between the affinity for the 5-HT3 receptors and the activity in the B-J reflex test (in vivo). From these data, it was suggested that our quinoline derivatives might interact with the 5-HT3 receptors in a different way from that of the reported 5-HT3 receptor antagonists presumably due to the presence of the heterogeneity of the 5-HT3 receptors between brain and heart.

  合成了一系列含有碱性氮杂双环烷基部分的1-烷基-2-氧-1,2-二氢喹啉-4-羧酸或2-烷氧基喹啉-4-羧酸的酯和酰胺，并评估了其对苯甲酸酯的亲和力。 [3H] quipazine标记的5-HT3受体。大多数酯显示出比恩丹西酮强效十倍的活性（1； Ki = 7.6 nM）。喹啉环1或2位的亲脂取代基增强了对受体的亲和力。其中，化合物21和37显示出最高的亲和力（分别为Ki ＝ 0.32和0.31nM）。另一方面，大多数酰胺的亲和力比酯低100倍。分子模型研究表明，19（酯）或31（酰胺）中的羰基部分与芳香环的平面不共面（偏差超过20度）。尽管某些选定的化合物在Bezold-Jarisch（BJ）反射测试中显示出强大的活性，但对5-HT3受体的亲和力与BJ反射测试（体内）的活性之间未观察到良好的相关性。从这些数据表明，我们的喹啉衍生物可能以与报道的5-HT3受体拮抗剂不同的方式与5-HT3受
• Antiemetic and migraine suppressing heterocyclic compounds and pharmaceutical compositions containing them
  申请人：KYOWA HAKKO KOGYO CO., LTD

  公开号：EP0458636A1

  公开（公告）日：1991-11-27

  Antiemetic and migraine suppressant compounds are disclosed being heterocyclic compounds of the wherein R¹ represents hydrogen, C₁-C₆ alkyl or C₆ - C₁₀; R² represents hydrogen, hydroxyl or C₁ - C₆ alkyl; A represents CH or N; X represents -O- or -NH-; R³ represents hydrogen, hydroxyl or C₁-C₆ alkyl; R⁴ represents C₁-C₆ alkyl; and n represents 0 or 1, and their pharmaceutically acceptable salts.

  所公开的止吐药和偏头痛抑制剂化合物属于以下杂环化合物 其中R¹代表氢、C₁-C₆烷基或C₆-C₁₀；R²代表氢、羟基或C₁-C₆烷基；A代表CH或N；X代表-O-或-NH-；R³ 代表氢、羟基或 C₁-C₆ 烷基；R⁴ 代表 C₁-C₆ 烷基；n 代表 0 或 1，以及它们的药学上可接受的盐类。
• Mulert, Chemische Berichte, 1906, vol. 39, p. 1904
  作者：Mulert

  DOI：——

  日期：——
• Meyer,H., Monatshefte fur Chemie, 1907, vol. 28, p. 38
  作者：Meyer,H.

  DOI：——

  日期：——