1-hydroxy-4-methyl-6-(naphthalen-2-yl)pyridin-2(1H)-one | 79438-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-hydroxy-4-methyl-6-(naphthalen-2-yl)pyridin-2(1H)-one
• 英文别名: 1-hydroxy-4-methyl-6-(2-naphthyl)-2-pyridone；1-Hydroxy-4-methyl-6-naphthalen-2-ylpyridin-2-one
• CAS: 79438-24-7
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: CROKGKMYGXHLHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙基萘 在 吡啶 、 盐酸羟胺 、 palladium diacetate 、 一氯化碘 、 三(2,6-二甲氧基苯基)磷 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 22.16h， 生成 1-hydroxy-4-methyl-6-(naphthalen-2-yl)pyridin-2(1H)-one
  参考文献：
  名称：

  Discovery of a novel series of N -hydroxypyridone derivatives protecting astrocytes against hydrogen peroxide-induced toxicity via improved mitochondrial functionality

  摘要：

  Astrocytes play a key role in brain homeostasis, protecting neurons against neurotoxic stimuli such as oxidative stress. Therefore, the neuroprotective therapeutics that enhance astrocytic functionality has been regarded as a promising strategy to reduce brain damage. We previously reported that ciclopirox, a well-known antifungal N-hydroxypyridone compound, protects astrocytes from oxidative stress by enhancing mitochondrial function. Using the N-hydroxypyridone scaffold, we have synthesized a series of cytoprotective derivatives. Mitochondrial activity assay showed that N-hydroxypyridone derivatives with biphenyl group have comparable to better protective effects than ciclopirox in astrocytes exposed to H2O2. N-hydroxypyridone derivatives, especially 11g, inhibited membrane-induced deterioration of mitochondrial membrane potential and oxygen consumption rate, and significantly improved cell viability of astrocytes. The results indicate that the N-hydroxypyridone motif can provide a novel cytoprotective scaffold for astrocytes via enhancing mitochondrial functionality. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.052

文献信息

• Lohaus; Dittmar, Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 8 a, p. 1311 - 1316
  作者：Lohaus、Dittmar

  DOI：——

  日期：——
• US3972888A
  申请人：——

  公开号：US3972888A

  公开（公告）日：1976-08-03
• US4185106A
  申请人：——

  公开号：US4185106A

  公开（公告）日：1980-01-22
• US4552754A
  申请人：——

  公开号：US4552754A

  公开（公告）日：1985-11-12
• US4711775A
  申请人：——

  公开号：US4711775A

  公开（公告）日：1987-12-08