7-氟-苯并[d]异噁唑-3-醇 | 855996-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 中文名称: 7-氟-苯并[d]异噁唑-3-醇
• 英文名称: 7-fluoro-benzo[d]isoxazol-3-ol
• 英文别名: 7-Fluorobenzo[d]isoxazol-3(2H)-one；7-fluoro-1,2-benzoxazol-3-one
• CAS: 855996-66-6
• 化学式: C₇H₄FNO₂
• 分子量: 153.113
• InChiKey: HHJCSHZCHBARDP-UHFFFAOYSA-N

物化性质

• 熔点：
  175-180 °C
• 密度：
  1.440±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-fluoro-N,2-dihydroxybenzamide 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 7-氟-苯并[d]异噁唑-3-醇
  参考文献：
  名称：

  Synthesis and Biological Evaluation of d-Amino Acid Oxidase Inhibitors

  摘要：

  D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a full agonist at the glycine site of the NMDA receptor. A series of benzo[d]isoxazol-3-ol derivatives were synthesized and evaluated as DAAO inhibitors. Among them, 5-chlorobenzo[d]isoxazol-3-ol (CBIO) potently inhibited DAAO with an IC(50) in the submicromolar range. Oral administration of CBIO in conjunction with D-serine enhanced the plasma and brain levels of D-serine in rats compared to the oral administration Of D-serine alone.

  DOI：

  10.1021/jm800200u

文献信息

• Benzo[d]isoxazol-3-ol DAAO inhibitors
  申请人：Fang Kevin Q.

  公开号：US20050143434A1

  公开（公告）日：2005-06-30

  Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia, or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutic amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein Z 1 is N or CR 3 ; Z 2 is N or CR 4 ; Z 3 is O or S; A is hydrogen, alkyl or M + ; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc or a mixture thereof; R 1 , R 2 , R 3 and R 4 are independently selected from hydrogen, alkyl, hydroxy alkoxy, aryl, acyl, halo, cyano, haloalkyl, NHCOOR 5 and SO 2 NH 2 ; R 5 is aryl, arylalkyl, heteroaryl or heteroarylalkyl; at least one of R 1 , R 2 , R 3 and R 4 is other than hydrogen; and at least one of Z 1 and Z 2 is other than N.

  增加D-丝氨酸浓度和减少D-丝氨酸氧化有毒产物浓度的方法，用于增强学习、记忆和/或认知，或用于治疗精神分裂症、阿尔茨海默病、共济失调、或神经病性疼痛，或预防神经退行性疾病特征性的神经元功能丧失，包括向需要治疗的受试者施用化合物I的治疗量，或其药学上可接受的盐或溶剂：其中Z1为N或CR3；Z2为N或CR4；Z3为O或S；A为氢、烷基或M+；M为铝、钙、锂、镁、钾、钠、锌或其混合物；R1、R2、R3和R4独立地选择自氢、烷基、羟基烷氧基、芳基、酰基、卤素、氰基、卤代烷基、NHCOOR5和SO2NH2；R5为芳基、芳基烷基、杂环芳基或杂环芳基烷基；R1、R2、R3和R4中至少有一个不是氢；且Z1和Z2中至少有一个不是N。
• BENZO [D]ISOXAZOL-3-OL DAAO INHIBITORS
  申请人：Sepracor Inc.

  公开号：EP1711478A2

  公开（公告）日：2006-10-18
• US7166725B2
  申请人：——

  公开号：US7166725B2

  公开（公告）日：2007-01-23
• [EN] BENZO[D]ISOXAZOL-3-OL DAAO INHIBITORS<br/>[FR] INHIBITEURS DE DAAO A BASE DE BENZO[D]ISOXAZOL-3-OL
  申请人：SEPRACOR INC

  公开号：WO2005066143A2

  公开（公告）日：2005-07-21

  Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia, or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutic amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: I wherein Z1 is N or CR3; Z2 is N or CR4; Z3 is O or S; A is hydrogen, alkyl or M+; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc or a mixture thereof; R1, R2, R3 and R4 are independently selected from hydrogen, alkyl, hydroxy alkoxy, aryl, acyl, halo, cyano, haloalkyl, NHCOOR5 and SO2NH2; R5 is aryl, arylalkyl, heteroaryl or heteroarylalkyl; at least one of R1, R2, R3 and R4 is other than hydrogen; and at least one of Z1 and Z2 is other than N.
• Synthesis and Biological Evaluation of <scp>d</scp>-Amino Acid Oxidase Inhibitors
  作者：Dana Ferraris、Bridget Duvall、Yao-Sen Ko、Ajit G. Thomas、Camilo Rojas、Pavel Majer、Kenji Hashimoto、Takashi Tsukamoto

  DOI：10.1021/jm800200u

  日期：2008.6.1

  D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a full agonist at the glycine site of the NMDA receptor. A series of benzo[d]isoxazol-3-ol derivatives were synthesized and evaluated as DAAO inhibitors. Among them, 5-chlorobenzo[d]isoxazol-3-ol (CBIO) potently inhibited DAAO with an IC(50) in the submicromolar range. Oral administration of CBIO in conjunction with D-serine enhanced the plasma and brain levels of D-serine in rats compared to the oral administration Of D-serine alone.