methyl (E)-3-(6-methoxynaphthalen-2-yl)but-2-enoate | 901766-67-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-3-(6-methoxynaphthalen-2-yl)but-2-enoate
• 英文别名: methyl (2E)-3-(6-methoxynaphthalen-2-yl)but-2-enoate
• CAS: 901766-67-4
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: VVRPZSLCXRAQQM-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(6-methoxynaphthalen-2-yl)but-2-enoate 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以65%的产率得到(E)-3-(6-methoxynaphthalen-2-yl) but-2-en-1-ol
  参考文献：
  名称：

  Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

  摘要：

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.008
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 6-甲氧基-2-乙酰萘 、 sodium methylate 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以96%的产率得到methyl (E)-3-(6-methoxynaphthalen-2-yl)but-2-enoate
  参考文献：
  名称：

  Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

  摘要：

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.008

文献信息

• NOVEL COMPOUNDS ADVANTAGEOUS IN THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISEASES AND DISORDERS
  申请人：Pesyan Amir

  公开号：US20110046128A1

  公开（公告）日：2011-02-24

  A series of novel compounds showing anticonvulsant, chemical countermeasure(s), and analgesic activities is described. Such pharmaceutically active compounds may also show utility in the treatment of other central nervous system (“CNS”) diseases and disorders, such as anxiety, depression, insomnia, migraine headaches, schizophrenia, Parkinson's disease, spasticity, Alzheimer's disease, and bipolar disorder. Furthermore, such compounds may additionally find utility as analgesics (e.g., for the treatment of chronic or neuropathic pain) and as neuroprotective agents useful in the treatment of stroke(s), chronic neurodegenerative diseases (such as Alzheimer's disease and Huntington's disease), and/or traumatic brain and/or spinal cord injuries. Moreover, these/such compounds may also be useful in the treatment of status epilepticus and/or as chemical countermeasures.

  本文介绍了一系列新型化合物，具有抗惊厥、化学对抗剂和镇痛活性。这些药物活性化合物也可能在治疗其他中枢神经系统（“CNS”）疾病和障碍方面发挥作用，如焦虑、抑郁、失眠、偏头痛、精神分裂症、帕金森病、痉挛、阿尔茨海默病和双相情感障碍。此外，这些化合物还可以作为镇痛剂（例如，用于慢性或神经性疼痛的治疗）和作为神经保护剂，有助于治疗中风、慢性神经退行性疾病（如阿尔茨海默病和亨廷顿病）以及创伤性脑和/或脊髓损伤。此外，这些化合物还可以用于治疗癫痫持续状态和/或作为化学对抗剂。
• Compounds advantageous in the treatment of central nervous system diseases and disorders
  申请人：AurimMed Pharma, Inc.

  公开号：US10793515B2

  公开（公告）日：2020-10-06

  A series of novel amides showing broad pharmaceutical activity. Compounds described herein are effective as anticonvulsants, chemical countermeasures, and analgesics. Such compounds also show, neuroprotective/neuroreparative effects and activity against spinal muscular atrophy. Such pharmaceutically active compounds show utility in the treatment of central nervous system (“CNS”) diseases and disorders, such as anxiety, depression, insomnia, migraine headaches, schizophrenia, neurodegenerative diseases (e.g., Parkinson's disease, Alzheimer's, ALS, and Huntington's disease) spasticity, and bipolar disorder. Furthermore, such compounds may additionally find utility as analgesics (e.g., for the treatment of chronic or neuropathic pain) and as neuroprotective agents useful in the treatment of stroke(s), and/or traumatic brain and/or spinal cord injuries.

  一系列新型酰胺具有广泛的药物活性。本文所述化合物可作为抗惊厥剂、化学对策和镇痛剂。这些化合物还具有神经保护/神经恢复作用，并对脊髓性肌肉萎缩具有活性。这类药物活性化合物可用于治疗中枢神经系统（CNS）疾病和失调，如焦虑症、抑郁症、失眠症、偏头痛、精神分裂症、神经退行性疾病（如帕金森氏病、阿尔茨海默氏症、渐冻人症和亨廷顿氏病）、痉挛症和躁狂症。此外，这类化合物还可作为镇痛剂（如治疗慢性疼痛或神经性疼痛）和神经保护剂用于治疗中风和/或创伤性脑损伤和/或脊髓损伤。
• US5032588A
  申请人：——

  公开号：US5032588A

  公开（公告）日：1991-07-16
• US9206143B2
  申请人：——

  公开号：US9206143B2

  公开（公告）日：2015-12-08
• US9212155B2
  申请人：——

  公开号：US9212155B2

  公开（公告）日：2015-12-15