1-(3,4-dimethoxy-5-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one | 923288-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dimethoxy-5-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one
• 英文别名: 1-(3,4-dimethoxy-5-nitro-phenyl)-3-dimethylamino-propen-1-one
• CAS: 923288-63-5
• 化学式: C₁₃H₁₆N₂O₅
• 分子量: 280.28
• InChiKey: NAOVJERJRFTLSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxy-5-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one 在 盐酸 、 过氧化脲素 、 三氟乙酸酐 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-[5-(3,4-dimethoxy-5-nitro-phenyl)-pyrazol-1-yl]-2-trifluoromethyl-pyridine 1-oxide
  参考文献：
  名称：

  WO2007/13830

  摘要：

  公开号：
• 作为产物：
  描述：

  1-(3,4-二甲氧基-5-硝基苯基)乙酮 、 N,N-二甲基甲酰胺二甲基缩醛 反应 5.0h， 以86%的产率得到1-(3,4-dimethoxy-5-nitrophenyl)-3-(dimethylamino)prop-2-en-1-one
  参考文献：
  名称：

  Discovery of a Long-Acting, Peripherally Selective Inhibitor of Catechol-O-methyltransferase

  摘要：

  Novel nitrocatechol-substituted heterocycles were designed and evaluated for their ability to inhibit catechol-O-methyltransferase (COMT). Replacement of the pyrazole core of the initial hit 4 with a 1,2,4-oxadiazole ring resulted in a series of compounds endowed with longer duration of COMT inhibition. Incorporation of a pyridine N-oxide residue at position 3 of the 1,2,4-oxadiazole ring led to analogue 37f, which was found to possess activity comparable to entacapone and lower toxicity in comparison to tolcapone. Lead structure 37f was systematically modified in order to improve selectivity and duration of COMT inhibition as well as to minimize toxicity. Oxadiazole 37d (2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine 1-oxide (BIA 9-1067)) was identified as a long-acting, purely peripheral inhibitor, which is currently under clinical evaluation as an adjunct to L-Dopa therapy of Parkinson's disease.

  DOI：

  10.1021/jm1001524

文献信息

• Pharmaceutical Compounds
  申请人：Learmonth David Alexander

  公开号：US20100168113A1

  公开（公告）日：2010-07-01

  This invention relates to novel substituted nitrocatechol derivatives, their use in the treatment of some central and peripheral nervous system disorders and pharmaceutical compositions containing them.

  这项发明涉及新型取代硝基邻苯二酚衍生物，其在治疗某些中枢和外周神经系统疾病中的用途，以及含有它们的药物组合物。
• Nitrocatechol Derivatives as Comt Inhibitors
  申请人：Learmonth David Alexander

  公开号：US20090054437A1

  公开（公告）日：2009-02-26

  New compounds of formula I are described. The compounds have potentially valuable pharmaceutical properties in the treatment of some central and peripheral nervous system disorders.

  本文介绍了一种I式化合物的新化合物。该化合物在治疗某些中枢和外周神经系统疾病方面具有潜在的有价值的药物特性。
• Nitrocatechol derivatives as COMT inhibitors
  申请人：Portela & CA., S.A.

  公开号：US08168793B2

  公开（公告）日：2012-05-01

  New compounds of formula I are described. The compounds have potentially valuable pharmaceutical properties in the treatment of some central and peripheral nervous system disorders.

  本文描述了公式I的新化合物。这些化合物在治疗某些中枢和周围神经系统疾病方面具有潜在的有价值的药物特性。
• NITROCATECHOL DERIVATIVES AS COMT INHIBITORS
  申请人：Learmonth David Alexander

  公开号：US20120196904A1

  公开（公告）日：2012-08-02

  New compounds of formula I are described. The compounds have potentially valuable pharmaceutical properties in the treatment of some central and peripheral nervous system disorders.

  本文描述了一种公式I的新化合物。这些化合物在治疗某些中枢和周围神经系统疾病方面具有潜在的有价值的药物特性。
• PHARMACEUTICAL COMPOUNDS
  申请人：BIAL - PORTELA & CA, S.A.

  公开号：US20140024682A1

  公开（公告）日：2014-01-23

  This invention relates to novel substituted nitrocatechol derivatives, their use in the treatment of some central and peripheral nervous system disorders and pharmaceutical compositions containing them.

  本发明涉及新的取代硝基间苯二酚衍生物，它们在治疗某些中枢和外周神经系统疾病中的应用以及包含它们的制药组合物。