3-(2-carboxymethylphenyl)acrylic acid | 183734-98-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2-carboxymethylphenyl)acrylic acid
• 英文别名: 3-[2-(Carboxymethyl)phenyl]prop-2-enoic acid
• CAS: 183734-98-7
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: KQFGETQDECOTLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-carboxymethylphenyl)acrylic acid 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 20.0 ℃ 、121.35 kPa 条件下， 以98%的产率得到3-[2-(羧甲基)苯基]丙酸
  参考文献：
  名称：

  Canton, Thierry; Boehme, Georg Andrees; Boireau, Alain, Journal of Pharmacology and Experimental Therapeutics, 2001, vol. 299, # 1, p. 314 - 322

  摘要：

  DOI：
• 作为产物：
  描述：

  邻溴苯乙酸 、 丙烯酸 在 palladium diacetate 三正丁胺 、 三(邻甲基苯基)磷 作用下， 以64%的产率得到3-(2-carboxymethylphenyl)acrylic acid
  参考文献：
  名称：

  Canton, Thierry; Boehme, Georg Andrees; Boireau, Alain, Journal of Pharmacology and Experimental Therapeutics, 2001, vol. 299, # 1, p. 314 - 322

  摘要：

  DOI：

文献信息

• Bioisosteres of 9-Carboxymethyl-4-oxo-imidazo[1,2- a ]indeno[1,2- e ]pyrazin-2-carboxylic acid derivatives. Progress towards selective, potent In Vivo AMPA antagonists with longer durations of action
  作者：Patrick Jimonet、Georg Andrees Bohme、Jean Bouquerel、Alain Boireau、Dominique Damour、Marc Williams Debono、Arielle Genevois-Borella、Jean-Claude Hardy、Philippe Hubert、Franco Manfré、Patrick Nemecek、Jeremy Pratt、John C.R. Randle、Yves Ribeill、Jean-Marie Stutzmann、Marc Vuilhorgne、Serge Mignani

  DOI：10.1016/s0960-894x(00)00592-8

  日期：2001.1

  A novel series of 2- and 9-disubstituted heterocyclic-fused 4-oxo-indeno[1,2-e]pyrazin derivatives was synthesized. One of them, the 9-(1 H-tetrazol-5-ylmethyl)-4-oxo-5,10-dihydroimidazo[1,2-a]indeno[1,2-e]pyrazin-2-yl phosphonic acid 4i exhibited a strong and a selective binding affinity for the AMPA receptor (IC50 = 13 nM) and demonstrated potent antagonist activity (IC50 = 6 nM) at the ionotropic AMPA receptor. This compound also displayed good anticonvulsant properties against electrically-induced convulsions after ip and iv administration with ED50 values between 0.8 and 1 mg/kg. Furthermore, a strong increase in potency was observed when given iv 3 h before test (ED50 = 3.5 instead of 25.6 mg/kg for the corresponding 9-carboxymethyl-2-carboxylic acid analogue). These data confirmed that there is an advantage in replacing the classical carboxy substituents by their bioisosteres such as tetrazole or phosphonic acid groups. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Canton, Thierry; Boehme, Georg Andrees; Boireau, Alain, Journal of Pharmacology and Experimental Therapeutics, 2001, vol. 299, # 1, p. 314 - 322
  作者：Canton, Thierry、Boehme, Georg Andrees、Boireau, Alain、Bordier, Francoise、Mignani, Serge、Jimonet, Patrick、Jahn, Ghafoor、Alavijeh, Mohammad、Stygall, James、Roberts, Simon、Brealey, Clive、Vuilhorgne, Marc、Debono, Marc-William、Le Guern, Sylvain、Laville, Michel、Briet, Dominique、Roux, Michel、Stutzmann, Jean-Marie、Pratt, Jeremy

  DOI：——

  日期：——