(S)-2-((2-硝基苯氧基)甲基)环氧乙烷 | 134598-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-2-((2-硝基苯氧基)甲基)环氧乙烷
• 英文名称: (2S)-2-[(2-nitrophenoxy)-methyl]oxirane
• 英文别名: (S)-glycidyl 2-nitrophenyl ether；(S)-1,2-epoxy-3-(2-nitrophenoxy)propane；(S)-1,2-epoxy-3-(o-nitrophenoxy)propane；(2S)-3-(2-nitrophenoxy)-1,2-epoxypropane；(S)-2-((2-Nitrophenoxy)methyl)oxirane；(2S)-2-[(2-nitrophenoxy)methyl]oxirane
• CAS: 134598-03-1
• 化学式: C₉H₉NO₄
• 分子量: 195.175
• InChiKey: SMKKEOQDQNCTGL-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((2-硝基苯氧基)甲基)环氧乙烷 、 3,4-二氯苯乙胺 在 ethylacetate-petroleum ether 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以to give the product (1.02 g, 99% yield, m.p. 73-74° C.) as a white solid的产率得到(S)-1-(2-nitrophenoxy)-3-(3,4-dichlorophenylethylamino)-2-propanol
  参考文献：
  名称：

  pH-dependent NMDA receptor antagonists

  摘要：

  NMDA受体阻滞剂，包括pH敏感的NMDA受体阻滞剂，被提供作为神经保护药物，适用于中风、创伤性脑损伤、癫痫和其他涉及脑或脊髓组织酸化的神经事件。本发明的组合物和方法用于治疗由NMDA受体激活引起的神经退行性疾病。所述化合物在具有低于正常pH的脑组织中具有增强的活性，这是由于病理条件（如中风引起的缺氧、创伤性脑损伤、可能发生于心脏手术期间的全局性缺血、呼吸停止后可能发生的缺氧、子痫前症、脊髓创伤、癫痫、慢性疼痛、血管性痴呆和胶质瘤）所致。本文所述的化合物还可用于预防帕金森病、阿尔茨海默病、亨廷顿舞蹈症、肌萎缩侧索硬化症和其他已知对使用NMDA受体阻滞剂治疗响应的神经退行性疾病患者的神经退行性。最好提供的化合物是变构NMDA抑制剂。

  公开号：

  US07375136B2
• 作为产物：
  描述：

  (S)-(+)- 间硝基苯磺酸缩水甘油酯 、 硝苯酚 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以90%的产率得到(S)-2-((2-硝基苯氧基)甲基)环氧乙烷
  参考文献：
  名称：

  Enantiomeric Propanolamines as selective N-Methyl-d-aspartate 2B Receptor Antagonists

  摘要：

  Enantiomeric propanolamines have been identified as a new class of NR2B-selective NMDA receptor antagonists. The most effective agents are biaryl structures, synthesized in six steps with overall yields ranging from 11-64%. The compounds are potent and selective inhibitors of NR2B-containing recombinant NMDA receptors with IC50 values between 30-100 nM. Potency is strongly controlled by substitution on both rings and the centrally located amine nitrogen. SAR analysis suggests that well-balanced polarity and chain-length factors provide the greatest inhibitory potency. Structural comparisons based on 3D shape analysis and electrostatic complementarity support this conclusion. The antagonists are neuroprotective in both in vitro and in vivo models of ischemic cell death. In addition, some compounds exhibit anticonvulsant properties. Unlike earlier generation NMDA receptor antagonists and some NR2B-selective antagonists, the present series of propanolamines does not cause increased locomotion in rodents. Thus, the NR2B-selective antagonists exhibit a range of therapeutically interesting properties.

  DOI：

  10.1021/jm8002153

文献信息

• Novel compounds
  申请人：——

  公开号：US20030144267A1

  公开（公告）日：2003-07-31

  The invention provides compounds of general formula (I) wherein Q, R, R 2 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  这项发明提供了一般式（I）的化合物，其中Q、R、R2、R4、R5、R6、R7和R8如规范中所定义，以及它们的制备方法、含有它们的药物组合物以及它们在治疗中的用途。
• Chiral Nanoporous Metal–Metallosalen Frameworks for Hydrolytic Kinetic Resolution of Epoxides
  作者：Chengfeng Zhu、Guozan Yuan、Xu Chen、Zhiwei Yang、Yong Cui

  DOI：10.1021/ja302340b

  日期：2012.5.16

  recyclable heterogeneous catalyst for hydrolytic kinetic resolution (HKR) of racemic epoxides with up to 99.5% ee. The MOF structure brings Co(salen) units into a highly dense arrangement and close proximity that enhances bimetallic cooperative interactions, leading to improved catalytic activity and enantioselectivity in HKR compared with its homogeneous analogues, especially at low catalyst/substrate ratios

  手性纳米多孔金属有机框架是通过使用二羧基功能化的手性 Ni(salen) 和 Co(salen) 配体构建的。基于 Co(salen) 的框架被证明是一种高效且可回收的多相催化剂，用于外消旋环氧化物的水解动力学拆分 (HKR)，ee 高达 99.5%。MOF 结构使 Co(salen) 单元形成高度密集的排列和紧密接近，增强了双金属协同相互作用，与均相类似物相比，HKR 的催化活性和对映选择性提高，尤其是在低催化剂/底物比的情况​​下。
• Bacillus alcalophilus MTCC10234 catalyzed enantioselective kinetic resolution of aryl glycidyl ethers
  作者：Neeraj Bala、Swapandeep Singh Chimni、Harvinder Singh Saini、Bhupinder Singh Chadha

  DOI：10.1016/j.molcatb.2009.12.019

  日期：2010.5

  The phenyl glycidyl ether derivatives have been kinetically resolved with the growing cells of Bacillus alcalophilus MTCC10234 yielding (S)-epoxides with up to >99% ee and (R)-diols with up to 89% ee. The enantiomeric ratio (E) of up to 67 has been obtained for biohydrolysis process. The effect of different substituents of phenyl glycidyl ether on the biocatalytic efficiency of B. alcalophilus MTCC10234

  苯缩水甘油醚衍生物已经与嗜碱芽孢杆菌MTCC10234的生长细胞动力学分离，产生了（S）-环氧化合物，其ee含量高达> 99％，（R）-二醇的ee含量高达89％。对于生物水解过程，已获得高达67的对映体比率（E）。苯基缩水甘油基醚的不同取代基对嗜酸芽孢杆菌MTCC10234的生物催化效率的影响表明，甲基和氯取代的芳基缩水甘油基醚衍生物较为可取，而硝基衍生物的转化速度较慢。将含有在两个邻位均具有甲基的大体积芳基的2，6-二甲基苯基缩水甘油醚用N-甲基-N-二甲基苯甲酸酯进行拆分。E  = 39。
• Ph-dependent nmda receptor antagonists
  申请人：——

  公开号：US20040138502A1

  公开（公告）日：2004-07-15

  NMDA receptor blockers, including pH-sensitive NMDA receptor blockers, are provided as neuroprotective drugs that are useful in stroke, traumatic brain injury, epilepsy, and other neurologic events that involve acidification of brain or spinal cord tissue. Compositions and methods of this invention are used for treating neurodegeneration resulting from NMDA receptor activation. The compounds described herein have enhanced activity in brain tissue having lower-than normal pH due to pathological conditions such as hypoxia resulting from stroke, traumatic brain injury, global ischemia tat may occur during cardiac surgery, hypoxia tat may occur following cessation of breathing, pre-eclampsia, spinal cord trauma, epilepsy, chronic pain, vascular dementia and glioma tumors. Compounds described herein are also useful in preventing neurodegeneration in patients with Parkinson's Alzheimer's, Huntington's chorea, ALS, and other neurodegenerative conditions known to the art to be responsive to treatment using NMDA receptor blockers. Preferably the compounds provided herein are allosteric NMDA inhibitors.

  NMDA受体阻滞剂，包括pH敏感的NMDA受体阻滞剂，被提供作为神经保护药物，可用于中风、创伤性脑损伤、癫痫和其他涉及大脑或脊髓组织酸化的神经事件。本发明的组合物和方法用于治疗由NMDA受体激活引起的神经退行性疾病。所述化合物在具有低于正常pH的脑组织中具有增强的活性，这是由于病理条件（如中风引起的低氧血症、创伤性脑损伤、在心脏手术期间可能发生的全局缺血、呼吸停止后可能发生的低氧血症、妊娠期高血压综合症、脊髓损伤、癫痫、慢性疼痛、血管性痴呆和胶质瘤等）。所述化合物也可用于预防帕金森病、阿尔茨海默病、亨廷顿舞蹈症、肌萎缩侧索硬化症和其他已知对使用NMDA受体阻滞剂治疗有反应的神经退行性疾病患者的神经退行性。优选地，本文提供的化合物是变构NMDA抑制剂。
• PH-dependent NMDA receptor antagonists
  申请人：Traynelis Stephen F.

  公开号：US20090023791A1

  公开（公告）日：2009-01-22

  NMDA receptor blockers, including pH-sensitive NMDA receptor blockers, are provided as neurprotective drugs that are useful in stroke, traumatic brain injury, epilepsy, and other neurologic events that involve acidification of brain or spinal cord tissue. Compositions and methods of this invention are used for treating neurodegeneration resulting from NMDA receptor activation. The compounds described herein have enhanced activity in brain tissue having lower than normal pH due to pathological conditions such as hypoxia resulting from stroke, traumatic brain injury, global ischemia that may occur during cardiac surgery, hypoxia that may occur following cessation of breathing, pre-eclampsia, spinal cord trauma, epilepsy, chrounic pain, vascular dementia and glioma rumors. Compounds described herein are also useful in preventing neurodegeneration in patients with Parkinson's Alzheimer's, Huntington's chorea, ALS, and other neurodegenerative conditions known to the art to be responsive to treatment using NMDA receptor blockers. Prefebably the compounds provided herein are allosteric NMDA inhibitors.

  NMDA受体阻滞剂，包括pH敏感的NMDA受体阻滞剂，作为神经保护药物提供，可用于中风、创伤性脑损伤、癫痫和其他涉及脑或脊髓组织酸化的神经事件。本发明的组合物和方法用于治疗由NMDA受体激活引起的神经退行性疾病。所述化合物在具有低于正常pH的脑组织中具有增强的活性，这是由于病理情况（如中风、创伤性脑损伤、可能发生于心脏手术期间的全球性缺血、呼吸停止后可能发生的低氧、先兆子痫、脊髓损伤、癫痫、慢性疼痛、血管性痴呆和胶质瘤）所致。所述化合物还可用于预防帕金森病、阿尔茨海默病、亨廷顿舞蹈症、肌萎缩侧索硬化症和其他已知对使用NMDA受体阻滞剂治疗有响应的神经退行性疾病患者的神经退行性。最好所提供的化合物是变构的NMDA抑制剂。