o-(1-carboxyethyl)cinnamic acid | 183735-93-5

• 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: o-(1-carboxyethyl)cinnamic acid
• 英文别名: 2-[2-[(E)-2-carboxyethenyl]phenyl]propanoic acid
• CAS: 183735-93-5
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: IDMQXYGRRTVHLR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  o-(1-carboxyethyl)cinnamic acid 在 palladium on activated charcoal sodium hydroxide 、 草酰氯 、 磷酸 、 五氯化磷 、 ammonium acetate 、 氢气 、 溴 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 5.0~130.0 ℃ 、121.35 kPa 条件下， 反应 7.0h， 生成 9-(1-Carboxy-ethyl)-4-oxo-5,10-dihydro-4H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and potent anticonvulsant activities of 4-oxo-imidazo[1,2-a]indeno[1,2-e]pyrazin-8- and -9-carboxylic (acetic) acid AMPA antagonists

  摘要：

  The over-stimulation of excitatory amino acid receptors such as the glutamate AMPA receptor has been suggested to be associated with neurodegenerative disorders. Here we describe an original series of readily water soluble 4-oxo-imidazo[1,2-a] indeno[1,2-e]pyrazin-8- and -9-carboxylic (acetic) acid derivatives. One of these compounds, 4f, exhibited nanomolar binding affinity, potent competitive antagonism at the ionotropic AMPA receptor and a long duration of anticonvulsant activity after administration by parenteral route in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00561-8
• 作为产物：
  描述：

  丙烯酸 、 2-(2-bromophenyl)propanoic acid 在 palladium diacetate 、 sodium carbonate 、 盐酸 作用下， 反应 35.0h， 以58%的产率得到o-(1-carboxyethyl)cinnamic acid
  参考文献：
  名称：

  Synthesis and potent anticonvulsant activities of 4-oxo-imidazo[1,2-a]indeno[1,2-e]pyrazin-8- and -9-carboxylic (acetic) acid AMPA antagonists

  摘要：

  The over-stimulation of excitatory amino acid receptors such as the glutamate AMPA receptor has been suggested to be associated with neurodegenerative disorders. Here we describe an original series of readily water soluble 4-oxo-imidazo[1,2-a] indeno[1,2-e]pyrazin-8- and -9-carboxylic (acetic) acid derivatives. One of these compounds, 4f, exhibited nanomolar binding affinity, potent competitive antagonism at the ionotropic AMPA receptor and a long duration of anticonvulsant activity after administration by parenteral route in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00561-8

文献信息

• 5H,10H-imidazo\x9b1,2-a!indeno\x9b1,2-e!pyrazin-4-one derivatives, preparation
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05902803A1

  公开（公告）日：1999-05-11

  Compounds of formula (I), wherein R is a hydrogen atom or a carboxy, alkoxycarbonyl, --CO--NR.sub.4 R.sub.5, --PO.sub.3 H.sub.2 or --CH.sub.2 OH radical, and R.sub.1 is an -alk-NH.sub.2, -alk-NH--CO--R.sub.3, -alk-COOR.sub.4, -alk-CO--NR.sub.5 R.sub.6 or --CO--NH--R.sub.7 radical. The compounds of formula (I) have valuable pharmacological properties and are antagonists of the .alpha.-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor also known as the quisqualate receptor. Furthermore, the compounds of formula (I) are non-competitive antagonists of the N-methyl-D-aspartame (NMDA) receptor and more specifically are ligands for NMDA receptor glycine modulator sites.

  式(I)化合物，其中R为氢原子或羧基、烷氧羰基、--CO--NR₄R₅、--PO₃H₂或--CH₂OH基团，R₁为-烷基-NH₂、-烷基-NH--CO--R₃、-烷基-COOR₄、-烷基-CO--NR₅R₆或--CO--NH--R₇基团。式(I)化合物具有宝贵的药理特性，是α-氨基-3-羟基-5-甲基-4-异噁唑丙酸(AMPA)受体即quisqualate受体的拮抗剂。此外，式(I)化合物是非竞争性N-甲基-D-天冬氨酸(NMDA)受体的拮抗剂，更具体地说是NMDA受体甘氨酸调节位点的配体。
• US5902803A
  申请人：——

  公开号：US5902803A

  公开（公告）日：1999-05-11
• US6057454A
  申请人：——

  公开号：US6057454A

  公开（公告）日：2000-05-02
• Synthesis and potent anticonvulsant activities of 4-oxo-imidazo[1,2-a]indeno[1,2-e]pyrazin-8- and -9-carboxylic (acetic) acid AMPA antagonists
  作者：Jeremy Pratt、Patrick Jimonet、Georg Andrees Bohme、Alain Boireau、Dominique Damour、Marc Williams Debono、Arielle Genevois-Borella、John C.R Randle、Yves Ribeill、Jean-Marie Stutzmann、Marc Vuilhorgne、Serge Mignani

  DOI：10.1016/s0960-894x(00)00561-8

  日期：2000.12

  The over-stimulation of excitatory amino acid receptors such as the glutamate AMPA receptor has been suggested to be associated with neurodegenerative disorders. Here we describe an original series of readily water soluble 4-oxo-imidazo[1,2-a] indeno[1,2-e]pyrazin-8- and -9-carboxylic (acetic) acid derivatives. One of these compounds, 4f, exhibited nanomolar binding affinity, potent competitive antagonism at the ionotropic AMPA receptor and a long duration of anticonvulsant activity after administration by parenteral route in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.