1-hydroxy-6-(4-methoxyphenyl)-4-methylpyridin-2(1H)-one | 50496-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-hydroxy-6-(4-methoxyphenyl)-4-methylpyridin-2(1H)-one
• 英文别名: 1-hydroxy-4-methyl-6-(4-methoxyphenyl)-2-pyridone；1-Hydroxy-6-(4-methoxyphenyl)-4-methylpyridin-2-one
• CAS: 50496-54-3
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: HLHNMVILCCFUCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-methyl-6-(4-methoxyphenyl)-2H-pyran-2-one 在 吡啶 、 盐酸羟胺 作用下， 反应 17.0h， 以50%的产率得到1-hydroxy-6-(4-methoxyphenyl)-4-methylpyridin-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
• Discovery of a novel series of N -hydroxypyridone derivatives protecting astrocytes against hydrogen peroxide-induced toxicity via improved mitochondrial functionality
  作者：Sarbjit Singh、Ja-Il Goo、Hyojin Noh、Sung Jae Lee、Myoung Woo Kim、Hyejun Park、Hitesh B. Jalani、Kyeong Lee、Chunsook Kim、Won-Ki Kim、Chung Ju、Yongseok Choi

  DOI：10.1016/j.bmc.2016.12.052

  日期：2017.2

  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.