2-acetyl-3-o-anisidino-acrylic acid ethyl ester | 142781-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-acetyl-3-o-anisidino-acrylic acid ethyl ester
• 英文别名: α-(2-Methoxy-phenyliminomethyl)-acetessigsaeure-aethylester；α-o-Anisidino-methylen-acetessigsaeure-aethylester；2-Acetyl-3-o-anisidino-acrylsaeure-aethylester；ethyl (2E)-2-[(2-methoxyanilino)methylidene]-3-oxobutanoate
• CAS: 142781-81-5
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: UHQIJDNQAGMPBZ-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-o-anisidino-acrylic acid ethyl ester 在 三氯氧磷 作用下， 以 二苯醚 为溶剂， 反应 1.75h， 生成 3-acetyl-4-chloro-8-methoxyquinoline
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4-(phenylamino)quinolines

  摘要：

  Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4-arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show th bearing such a substituent, only a particular combination of properties provides high activity, both in as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a pi-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK&F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00096a018
• 作为产物：
  描述：

  邻甲苯胺 、 2-乙氧亚甲基乙酰乙酸乙酯 反应 0.17h， 生成 2-acetyl-3-o-anisidino-acrylic acid ethyl ester
  参考文献：
  名称：

  Reversible inhibitors of the gastric (H+/K+)-ATPase. 3. 3-Substituted-4-(phenylamino)quinolines

  摘要：

  Previously, gastric (H+/K+)-ATPase inhibitors such as 2 have been prepared as analogues of 1a on the presumption that the 3-carbethoxy substituent plays a key role in establishing the orientation of the 4-arylamino group. In this paper we explore further the contribution made to activity by the quinoline 3-substituent. We show th bearing such a substituent, only a particular combination of properties provides high activity, both in as inhibitors of gastric acid secretion in vivo. The ability of the substituent to affect activity by restricting rotation about the C(quin)-N bond through a combination of both a pi-electron withdrawal and hydrogen bonding is supported by the current study. However, high activity is only achieved if the effect of this group on the quinoline pK(a) is kept to a minimum. 3-Acyl substituents provide an optimum combination of electronic properties. From this series, compound 17c (SK&F 96067) was shown to be a potent inhibitor of histamine-stimulated gastric acid secretion oral dosing in the Heidenhain pouch dog and was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00096a018

文献信息

• Mapata; Desai, Journal of the Indian Chemical Society, 1954, vol. 31, p. 951,955
  作者：Mapata、Desai

  DOI：——

  日期：——
• Dains; Brown, Journal of the American Chemical Society, 1909, vol. 31, p. 1152
  作者：Dains、Brown

  DOI：——

  日期：——
• Derivatives of 4-aminoquinoline and their use as medicaments
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0259174B1

  公开（公告）日：1992-03-18
• 4-OXO-1, 4-DIHYDROQUINOLINE-3-CARBOXAMIDE AS SELECTIVE LIGAND FOR CANNABINOID RECEPTOR 2 FOR DIAGNOSIS AND THERAPY
  申请人：ETH ZURICH

  公开号：US20170174632A1

  公开（公告）日：2017-06-22

  The present invention is directed to new compounds selectively binding the cannabinoid 2 receptor. In addition, the invention relates to the use of said compounds for determining cannabinoid receptor 2 (CB2)-selective receptor localization and density, preferably in the central nervous system (CNS), the peripheral nervous system (PNS), heart, liver, gastrointestinal tract, spleen, pancreas, kidney, testis, ovary and/or the prostate. Moreover, the invention pertains to the use of said compounds in the diagnosis, prophylaxis and/or therapy of CB2 receptor-related diseases.
• US4806549A
  申请人：——

  公开号：US4806549A

  公开（公告）日：1989-02-21