(3-Benzenesulfonyloxy-isoxazol-5-yl)-bromo-acetic acid | 253123-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-Benzenesulfonyloxy-isoxazol-5-yl)-bromo-acetic acid
• CAS: 253123-10-3
• 化学式: C₁₁H₈BrNO₆S
• 分子量: 362.158
• InChiKey: XVQIGLANASEWBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  106.7
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3-Benzenesulfonyloxy-isoxazol-5-yl)-bromo-acetic acid 在 Amberlite 120 、 氢气 作用下， 以 水 为溶剂， 反应 48.0h， 生成 2-ethylamino-2-(3-hydroxy-5-isoxazolyl)acetic acid
  参考文献：
  名称：

  Synthesis and pharmacology of N-alkylated derivatives of the excitotoxin ibotenic acid

  摘要：

  Three amino-alkylated derivatives of the naturally occurring excitatory amino acid (EAA) receptor agonist ibotenic acid (Ibo) have been synthesized and tested pharmacologically. N-Methyl-Ibo (la) and N-ethyl-Ibo(lb) were shown to be agonists at NMDA receptors (EC50 = 140 and 320 mu M, respectively), though with activities considerably lower than Ibo (EC50 = 9.6 mu M). N-Benzyl-Ibo (Ic) was inactive at ionotropic EAA receptors and all three compounds were, in contrast to Ibo, inactive at metabotropic EAA receptors. Molecular mechanics calculations have been performed on Ibo, la-c and the potent NMDA agonist 2-amino-2-(3-hydroxy-5-methyl-4-isoxazolyl)acetic acid (AMAA) in order to elucidate the observed structure-activity data. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00264-9
• 作为产物：
  描述：

  2-bromo-2-(3-benzenesulfoxy-5-isoxazolyl)acetic acid ethyl ester 在 盐酸 、 溶剂黄146 作用下， 反应 55.0h， 生成 (3-Benzenesulfonyloxy-isoxazol-5-yl)-bromo-acetic acid
  参考文献：
  名称：

  Synthesis and pharmacology of N-alkylated derivatives of the excitotoxin ibotenic acid

  摘要：

  Three amino-alkylated derivatives of the naturally occurring excitatory amino acid (EAA) receptor agonist ibotenic acid (Ibo) have been synthesized and tested pharmacologically. N-Methyl-Ibo (la) and N-ethyl-Ibo(lb) were shown to be agonists at NMDA receptors (EC50 = 140 and 320 mu M, respectively), though with activities considerably lower than Ibo (EC50 = 9.6 mu M). N-Benzyl-Ibo (Ic) was inactive at ionotropic EAA receptors and all three compounds were, in contrast to Ibo, inactive at metabotropic EAA receptors. Molecular mechanics calculations have been performed on Ibo, la-c and the potent NMDA agonist 2-amino-2-(3-hydroxy-5-methyl-4-isoxazolyl)acetic acid (AMAA) in order to elucidate the observed structure-activity data. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00264-9

文献信息

• Synthesis and biological activity of the N-alkyl derivatives of ibotenic acid
  作者：M. A. Dumpis、H. Brauner-Osborn、U. Madsen、L. B. Piotrovskii

  DOI：10.1007/bf02508408

  日期：1999.1

  is the synthesis and characterization of new compounds capable of acting upon the system of excitatory amino acids (EAAs) in the CNS of mammals. The EAA-ergic structures play an important role in the regulation of physiological and pathophysiological processes in the brain, which is confirmed by the fact that dicarboxylic acids act as mediators in associative, emotional, vegetative, and some other CNS

  现代药物化学和神经药理学中的一个重要当前问题是能够作用于哺乳动物中枢神经系统兴奋性氨基酸 (EAA) 系统的新化合物的合成和表征。EAA 能结构在大脑生理和病理生理过程的调节中发挥重要作用，这一点得到了以下事实的证实：二羧酸在联想、情绪、植物和其他一些中枢神经系统功能中充当介质 [1-3] . EAA受体可分为两组。第一组包括三种类型的离子型受体-N-甲基-D-天冬氨酸(NMDA)型、2-氨基-3-(3-羟基-5-甲基-4异恶唑基)丙酸(AMPA)型和红藻氨酸型. 第二组包含代谢型受体 (mGluR 1 8) [4 6]。在众多的天然氨基酸中，通常表现出EAA受体非选择性激动剂的特性，有一个-2-氨基-2-(3-羟基-5isoxazolyl)乙酸(或ibotenie)酸(I)值得特别关注。最初从毒蝇伞真菌中分离出的酸 I 可以被认为是谷氨酸的构象刚性类似物，其中 3-羟基异恶唑循环作为 7-羧基的生物等排片段。这种酸主要与