ethyl 3-chloromethyl-5-methyl-4-isoxazolecarboxylate | 266341-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-chloromethyl-5-methyl-4-isoxazolecarboxylate
• 英文别名: ethyl 3-(chloromethyl)-5-methyl-1,2-oxazole-4-carboxylate
• CAS: 266341-73-5
• 化学式: C₈H₁₀ClNO₃
• mdl: MFCD24463961
• 分子量: 203.625
• InChiKey: PPFRRWXGHMKDLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-chloromethyl-5-methyl-4-isoxazolecarboxylate 在 盐酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3-(2-Amino-2-carboxy-ethyl)-5-methyl-isoxazole-4-carboxylic acid
  参考文献：
  名称：

  Ionotropic excitatory amino acid receptor ligands. Synthesis and pharmacology of a new amino acid AMPA antagonist

  摘要：

  We have previously described the potent and selective (RS)-2-amino-3-(3-hydroxy-5-methyl-5-isoxazolyl)propionic acid (AMPA) receptor agonist, (RS)-2-amino-3-(3-carboxy-5-merhyl-4-isoxazolyl)propionic acid (ACPA), and the AMPA receptor antagonist (RS)-2-amino3-[3-(carboxymethoxy)-5-methyl-4-isoxazolyl]propionic acid (AMOA). Using these AMPA receptor ligands as leads, a series of compounds have been developed as tools for further elucidation of the structural requirements for activation and blockade of AMPA receptors. The synthesized compounds have been tested for activity at ionotropic excitatory amino acid (EAA) receptors using receptor binding and electrophysiological techniques, and for activity at metabotropic EAA receptors using second messenger assays. Compounds 1 and 4 were essentially inactive. (RS)-2-Amino-3-[3-(2-carboxyethyl)-5-methyl-4-isoxazoly]propionic acid (ACMP, 2), on the other hand, was shown to be a selective AMPA receptor antagonist (IC50 = 73 mu M), more potent in electrophysiological experiments than AMOA (IC50 = 320 mu M). The isomeric analogue of 2, compound 5, did not show AMPA antagonist effects, but was a weak NMDA receptor antagonist (IC50 = 540 mu M). Finally, compound 3, which is an isomer of ACPA, turned out to be a very weak NMDA antagonist, and an AMPA receptor agonist approximately 1 000 times weaker than ACPA. None of the compounds showed agonist or antagonist effects at metabotropic EAA receptors. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00104-5
• 作为产物：
  描述：

  ethyl 3-hydroxymethyl-5-methyl-4-isoxazolecarboxylate 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 ethyl 3-chloromethyl-5-methyl-4-isoxazolecarboxylate
  参考文献：
  名称：

  Ionotropic excitatory amino acid receptor ligands. Synthesis and pharmacology of a new amino acid AMPA antagonist

  摘要：

  We have previously described the potent and selective (RS)-2-amino-3-(3-hydroxy-5-methyl-5-isoxazolyl)propionic acid (AMPA) receptor agonist, (RS)-2-amino-3-(3-carboxy-5-merhyl-4-isoxazolyl)propionic acid (ACPA), and the AMPA receptor antagonist (RS)-2-amino3-[3-(carboxymethoxy)-5-methyl-4-isoxazolyl]propionic acid (AMOA). Using these AMPA receptor ligands as leads, a series of compounds have been developed as tools for further elucidation of the structural requirements for activation and blockade of AMPA receptors. The synthesized compounds have been tested for activity at ionotropic excitatory amino acid (EAA) receptors using receptor binding and electrophysiological techniques, and for activity at metabotropic EAA receptors using second messenger assays. Compounds 1 and 4 were essentially inactive. (RS)-2-Amino-3-[3-(2-carboxyethyl)-5-methyl-4-isoxazoly]propionic acid (ACMP, 2), on the other hand, was shown to be a selective AMPA receptor antagonist (IC50 = 73 mu M), more potent in electrophysiological experiments than AMOA (IC50 = 320 mu M). The isomeric analogue of 2, compound 5, did not show AMPA antagonist effects, but was a weak NMDA receptor antagonist (IC50 = 540 mu M). Finally, compound 3, which is an isomer of ACPA, turned out to be a very weak NMDA antagonist, and an AMPA receptor agonist approximately 1 000 times weaker than ACPA. None of the compounds showed agonist or antagonist effects at metabotropic EAA receptors. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00104-5

文献信息

• Compounds and Methods for Treating Bacterial Infections
  申请人：NEW YORK UNIVERSITY

  公开号：US20210214359A1

  公开（公告）日：2021-07-15

  This invention relates to compounds, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating bacterial infections. This invention relates more particularly to compounds and pharmaceutical compositions thereof, methods of inhibiting H 2 S-producing enzymes with the compounds, and methods of treating bacterial infections with the compounds.