α-amino-3-hydroxy-4-isooxazolepropanoic acid | 77006-28-1

• 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: α-amino-3-hydroxy-4-isooxazolepropanoic acid
• 英文别名: α-amino-3-hydroxy-4-isoxazolepropionic acid；(RS)-2-amino-3-(3-hydroxyisoxazol-4-yl)propionic acid；α-amino-3-hydroxy-4-isoxazolepropionic acid；α-Amino-3-hydroxy-4-isoxazolpropionic acid；alpha-amino-3-hydroxy-4-isoxazolepropionic acid；3-(3-Hydroxy-1,2-oxazol-4-yl)alanine；2-amino-3-(3-oxo-1,2-oxazol-4-yl)propanoic acid
• CAS: 77006-28-1
• 化学式: C₆H₈N₂O₄
• 分子量: 172.141
• InChiKey: ZKLGQYGPVBFAQQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  12
• 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：

  2-Acetylamino-2-(2-methoxymethyl-3-oxo-2,3-dihydro-isoxazol-4-ylmethyl)-malonic acid dimethyl ester 以 三氟乙酸 为溶剂， 反应 48.0h， 以23%的产率得到α-amino-3-hydroxy-4-isooxazolepropanoic acid
  参考文献：
  名称：

  Excitatory amino-acid receptor agonists. Synthesis and pharmacology of analogues of 2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid

  摘要：

  We have previously proposed the existence of a lipophilic cavity of the 2-amino-3-(3-hydroxy-5-methylisoxazol4-yl)propionic acid (AMPA) receptor recognition site capable of accommodating alkyl substituents of limited size in the 5-position of the isoxazole ring. In order to indirectly elucidate the approximate extent of this proposed cavity we have synthesized and pharmacologically characterized a number of AMPA analogues. For most of these AMPA analogues, a positive correlation between AMPA receptor affinity and agonist effect was observed. The only exception was demethyl-AMPA (8a), which showed relatively high AMPA receptor affinity (IC50 = 0.27 mu M) but remarkably weak agonist potency (EC50 = 900 mu M). Whereas the ethyl analogue of AMPA (Et-AMPA) (IC50 = 0.030 mu M; EC50 = 2.3 mu M) has previously been shown to be slightly more potent than AMPA (IC50 = 0.040 mu M; EC50 = 3.5 mu M), substitutions of a propyl or a butyl group for the methyl group of AMPA to give 8b (IC50 = 0.090 mu M; EC50 = 5.0 mu M) or 8f (IC50 = 1.0 mu M; EC50 = 32 mu M), respectively, result in progressive loss of the AMPA agonist effect. Analogues containing larger groups, such as isopentyl (8e), 1-propylbutyl (8g), 2,2-dimethylpropyl (8h), or benzyl (14) groups, were very weak or totally inactive as AMPA receptor ligands.

  DOI：

  10.1016/s0223-5234(97)89085-x

文献信息

• Choline derivative for the treatment of alzheimer's disease
  申请人：——

  公开号：US20030166721A1

  公开（公告）日：2003-09-04

  Choline derivatives useful in the treatment of the diseases related with central cholinergic deficit

  胆碱衍生物对治疗与中枢胆碱能缺陷相关的疾病有用。
• Systems and methods for cardiac plexus neuromodulation
  申请人：Tulavi Therapeutics, Inc.

  公开号：US11446359B2

  公开（公告）日：2022-09-20

  Methods, devices and systems are described for decreasing the activity of the sympathetic nervous innervation to and from the lungs and the vessels supplying the lungs to treat pulmonary medical conditions such as asthma. In one embodiment, the method may involve advancing an intravascular instrument to a target location in a blood vessel within the intercostal vasculature to ablate either or both the sympathetic afferent and efferent nerves lying within the paravertebral gutter including the visceral fibers that travel to the cardiothoracic cavity and abdominopelvic viscera and the T1 to T4/5 sympathetic chain. In another embodiment, an intravascular instrument may be advanced to the bronchial vessels to ablate either or both the sympathetic afferent and efferent nerves in and around the posterior pulmonary plexus. In one embodiment the ablative agent is a neurolytic agent delivered in a gel. This approach may be utilized to treat other cardiac and pulmonary diseases.

  所述方法、装置和系统用于降低进出肺部和供应肺部的血管的交感神经神经支配的活性，以治疗哮喘等肺部疾病。在一个实施方案中，该方法可能涉及将血管内仪器推进到肋间血管内的目标位置，以消融位于椎旁沟内的交感神经传入和传出神经，包括通向心胸腔和腹盆腔内脏的内脏纤维以及 T1 至 T4/5 交感神经链。在另一个实施方案中，可将血管内器械推进到支气管，以消融后肺丛及其周围的交感传入和传出神经中的一条或两条。在一个实施方案中，消融剂是以凝胶形式递送的神经溶解剂。这种方法可用于治疗其他心脏和肺部疾病。
• CHOLINE DERIVATIVES FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：Universita' Degli Studi Di Roma "La Sapienza"

  公开号：EP1274674A1

  公开（公告）日：2003-01-15
• SYSTEMS AND MEHTODS FOR SYMPATHETIC CARDIOPULMONARY NEUROMODULATION
  申请人：Reflex Medical Inc.

  公开号：EP3288626A1

  公开（公告）日：2018-03-07
• SYSTEMS AND METHODS FOR GEL-BASED NEUROMODULATION
  申请人：Tulavi Therapeutics, Inc.

  公开号：EP3764990A1

  公开（公告）日：2021-01-20