3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)pyridine 1-oxide | 923288-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)pyridine 1-oxide
• 英文别名: 3-Nitro-5-[3-(1-oxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-benzene-1,2-diol；2-Hydroxy-6-nitro-4-[3-(1-oxo-1lambda~5~-pyridin-3-yl)-1,2,4-oxadiazol-5(2H)-ylidene]cyclohexa-2,5-dien-1-one；3-nitro-5-[3-(1-oxidopyridin-1-ium-3-yl)-1,2,4-oxadiazol-5-yl]benzene-1,2-diol
• CAS: 923288-11-3
• 化学式: C₁₃H₈N₄O₆
• 分子量: 316.23
• InChiKey: PMBPYLYFNUWBGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N'-羟基-3-吡啶甲脒1-氧化物 在 aluminum (III) chloride 吡啶 、 三溴化硼 、 N,N'-羰基二咪唑 作用下， 以 1,2-dichloromethane 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)pyridine 1-oxide
  参考文献：
  名称：

  WO2007/13830

  摘要：

  公开号：

文献信息

• 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.

  本文描述了一些公式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。
• Nitrocatechol derivatives as COMT inhibitors
  申请人：BIAL—PORTELA & CA, S.A.

  公开号：US10336740B2

  公开（公告）日：2019-07-02

  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宝贵药用价值。
• Discovery of a Long-Acting, Peripherally Selective Inhibitor of Catechol-<i>O</i>-methyltransferase
  作者：László E. Kiss、Humberto S. Ferreira、Leonel Torrão、Maria João Bonifácio、P. Nuno Palma、Patrício Soares-da-Silva、David A. Learmonth

  DOI：10.1021/jm1001524

  日期：2010.4.22

  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.
• EP2301934A1
  申请人：——

  公开号：EP2301934A1

  公开（公告）日：2011-03-30