(RS)-2-Amino-3-(4-chloro-3-hydroxy-5-isoxazolyl)propionic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (RS)-2-Amino-3-(4-chloro-3-hydroxy-5-isoxazolyl)propionic acid
• 英文别名: 2-Amino-3-(4-chloro-3-hydroxy-5-isoxazolyl)propionic acid；Cl-HIBO；2-amino-3-(4-chloro-3-oxo-1,2-oxazol-5-yl)propanoic acid
• 化学式: C₆H₇ClN₂O₄
• 分子量: 206.586
• InChiKey: FDSXCQTXUSQQFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-acetylamino-2-methoxycarbonyl-3-(4-chloro-3-methoxy-5-isoxazolyl)propionate 在 盐酸 作用下， 反应 24.0h， 以75%的产率得到(RS)-2-Amino-3-(4-chloro-3-hydroxy-5-isoxazolyl)propionic acid
  参考文献：
  名称：

  Design, Synthesis, and Pharmacology of a Highly Subtype-Selective GluR1/2 Agonist, (RS)-2-Amino-3-(4-chloro-3-hydroxy-5-isoxazolyl)propionic Acid (Cl-HIBO)

  摘要：

  On the basis of structural studies, chloro-homoibotenic acid(Cl-HIBO) was designed and synthesized. Cl-HIBO was characterized in binding and electrophysiology experiments on native and cloned subtypes of GluRs. Electrophysiological selectivities ranged from 275 to 1600 for GluR1/2 over GluR3/4. The potent AMPA receptor activity was strongly desensitizing and the neurotoxicity similar to AMPA. Thus, Cl-HIBO is the most subtype selective agonist reported to date on GluR1/2, and offers a new standard for selectively studying subtypes of AMPA receptors.

  DOI：

  10.1021/jm020588f

文献信息

• METHODS AND ASSAYS FOR DETECTING AND TREATING HYPOGLYCEMIA
  申请人：University of Miami

  公开号：EP2254568A2

  公开（公告）日：2010-12-01
• COMPOUND THAT ACTIVATES AN AMPA/KAINATE TYPE RECEPTOR FOR TREATING HYPOGLYCEMIA
  申请人：University of Miami

  公开号：EP2254568B1

  公开（公告）日：2017-06-07
• Methods and Assays for Detecting and Treating Hypoglycemia
  申请人：Berggren Per-Olof

  公开号：US20110021584A1

  公开（公告）日：2011-01-27

  Methods for regulating glucagon release and of treating hypoglycemia, and for screening drug candidates for treating hypoglycemia. The methods are useful for treating diabetes mellitus and screening drug candidates for potential efficacy.
• US8466185B2
  申请人：——

  公开号：US8466185B2

  公开（公告）日：2013-06-18
• [EN] METHODS AND ASSAYS FOR DETECTING AND TREATING HYPOGLYCEMIA<br/>[FR] PROCÉDÉS ET DOSAGES POUR DÉTECTER ET TRAITER UNE HYPOGLYCÉMIE
  申请人：UNIV MIAMI

  公开号：WO2009114718A2

  公开（公告）日：2009-09-17

  Methods for regulating glucagon release and of treating hypoglycemia, and for screening drug candidates for treating hypoglycemia. The methods are useful for treating diabetes mellitus and screening drug candidates for potential efficacy.