3-methoxy-N-(oxiran-2-ylmethyl)aniline | 1262543-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxy-N-(oxiran-2-ylmethyl)aniline
• CAS: 1262543-66-7
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: XSBMQCVLZJQUNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-N-(oxiran-2-ylmethyl)aniline 在 二苯硫醚 、 palladium on activated carbon 、 氢气 、 sodium hydride 、 戴斯-马丁氧化剂 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)-propan-2-one
  参考文献：
  名称：

  Aminopropyl carbazole analogues as potent enhancers of neurogenesis

  摘要：

  Neural stem cells are multipotent and self-renewing cells that can differentiate into new neurons and hold great promise for treating various neurological disorders including multiple sclerosis, Parkinson's disease, and Alzheimer's disease. Small molecules that can trigger neurogenesis and neuroprotection are particularly useful not only because of their therapeutic implications but also because they can provide an invaluable tool to study the mechanisms of neurogenesis. In this report, we have developed and screened 25 aminopropyl carbazole derivatives that can enhance neurogenesis of cultured neural stem cells. Among these analogues, compound 9 demonstrated an excellent proneurogenic and neuroprotective activity with no apparent toxicity. We believe that compound 9 can serve as an excellent lead to develop various analogues and to study the underlying mechanisms of neurogenesis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.066
• 作为产物：
  描述：

  1-chloro-3-((3-methoxyphenyl)amino)propan-2-ol 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以99%的产率得到3-methoxy-N-(oxiran-2-ylmethyl)aniline
  参考文献：
  名称：

  二氧化碳连续有机催化流动合成2-取代恶唑烷酮

  摘要：

  聚苯乙烯负载的 1,5,7-triazabicyclodec-5-ene (TBD) 被用作高度可回收且稳定的催化剂，用于将环氧胺转化为各种 2-恶唑烷酮支架。该方法将使用 CO 2作为有吸引力、廉价且丰富的 C 1源与无卤有机催化连续流动方法相结合，以促进有效合成药学相关的 2-取代恶唑烷酮小型库，包括已知的药物 Toloxatone . 包含同一批固定化催化剂的填充床反应器可用于在两周内连续合成一系列杂环产品，而催化活性不会发生显着变化。

  DOI：

  10.1039/d2gc00503d

文献信息

• Pro-Neurogenic Compounds
  申请人：Board of Regents of The University of Texas System

  公开号：US20140057900A1

  公开（公告）日：2014-02-27

  Compounds and methods for stimulating neurogenesis (e.g., post-natal neurogenesis, including post-natal hippocampal and hypothalamic neurogenesis) and/or protecting neuronal cell from cell death are disclosed herein. In vivo activity tests suggest that these compounds may have therapeutic benefits in neuropsychiatric and/or neurodegenerative diseases such as schizophrenia, major depression, bipolar disorder, normal aging, epilepsy, traumatic brain injury, post-traumatic stress disorder, Parkinson's disease, Alzheimer's disease, Down syndrome, spinocerebellar ataxia, amyotrophic lateral sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of a neuro-active drug, retinal degeneration, spinal cord injury, peripheral nerve injury, physiological weight loss associated with various conditions, as well as cognitive decline associated with normal aging, chemotherapy, and the like.

  本发明公开了刺激神经发生（例如，产后神经发生，包括产后海马和下丘脑神经发生）和/或保护神经细胞免于细胞死亡的化合物和方法。体内活性测试表明，这些化合物可能在精神神经疾病和/或神经退行性疾病中具有治疗益处，例如精神分裂症、重度抑郁症、双相情感障碍、正常衰老、癫痫、创伤性脑损伤、创伤后应激障碍、帕金森病、阿尔茨海默病、唐氏综合症、脊髓小脑共济失调、肌萎缩侧索硬化症、亨廷顿病、中风、放射治疗、慢性压力、滥用神经活性药物、视网膜退化、脊髓损伤、周围神经损伤、与各种情况相关的生理体重减轻，以及与正常衰老、化疗等相关的认知衰退。
• Stereocontrolled, Divergent, Al(lll)-Catalyzed Coupling of Chiral <i>N</i>-Aryl Epoxy Amines and CO₂
  作者：Yuseop Lee、Jonghoon Choi、Hyunwoo Kim

  DOI：10.1021/acs.orglett.8b02186

  日期：2018.8.17

  achieved between N-aryl epoxy amines and CO2. By using two different cocatalysts, tetrabutylammonium iodide (TBAI) or 4-dimethylaminopyridine (DMAP) together with an Al(III) Lewis acid, cyclic carbonates or oxazolidinones were selectively produced through two distinct reaction pathways, respectively. The proposed reaction mechanism was supported by the stereochemical determination of the products. A

  N-芳基环氧胺与CO 2之间发生了发散性偶联反应。通过使用两种不同的助催化剂，碘化四丁基铵碘化物（TBAI）或4-二甲基氨基吡啶（DMAP）以及Al（III）Lewis酸，分别通过两种不同的反应途径选择性地生产环状碳酸酯或恶唑烷酮。所提出的反应机理得到产物的立体化学测定的支持。成功实现了克利奈唑胺的克级生产。
• Development of Proneurogenic, Neuroprotective Small Molecules
  作者：Karen S. MacMillan、Jacinth Naidoo、Jue Liang、Lisa Melito、Noelle S. Williams、Lorraine Morlock、Paula J. Huntington、Sandi Jo Estill、Jamie Longgood、Ginger L. Becker、Steven L. McKnight、Andrew A. Pieper、Jef K. De Brabander、Joseph M. Ready

  DOI：10.1021/ja108211m

  日期：2011.2.9

  Degeneration of the hippocampus is associated with Alzheimer's disease and occurs very early in the progression of the disease. Current options for treating the cognitive symptoms associated with Alzheimer's are inadequate, giving urgency to the search for novel therapeutic strategies. Pharmacologic agents that safely enhance hippocampal neurogenesis may provide new therapeutic approaches. We discovered the first synthetic molecule, named P7C3, which protects newborn neurons from apopotic cell death, and thus promotes neurogenesis in mice and rats in the subgranular zone of the hippocampal dentate gyrus, the site of normal neurogenesis in adult mammals. We describe the results of a medicinal chemistry campaign to optimize the potency, toxicity profile, and stability of P7C3. Systematic variation of nearly every position of the lead compound revealed elements conducive toward increases in activity and regions subject to modification. We have discovered compounds that are orally available, nontoxic, stable in mice, rats, and cell culture, and capable of penetrating the blood brain barrier. The most potent compounds are active at nanomolar concentrations. Finally, we have identified derivatives that may facilitate mode-of-action studies through affinity chromatography or photo-cross-linking.
• PRO-NEUROGENIC COMPOUNDS
  申请人：Board of Regents of the University of Texas System

  公开号：EP2887803A1

  公开（公告）日：2015-07-01
• US9701676B2
  申请人：——

  公开号：US9701676B2

  公开（公告）日：2017-07-11