4-methyl-6-(4-methoxyphenyl)-2H-pyran-2-one | 50496-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methyl-6-(4-methoxyphenyl)-2H-pyran-2-one
• 英文别名: 6-(4-methoxyphenyl)-4-methyl-2H-pyran-2-one；6-(4-Methoxyphenyl)-4-methylpyran-2-one
• CAS: 50496-61-2
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: VTINYVKACZCILS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-iodo-6-(4-methoxyphenyl)-4-methyl-2H-pyran-2-one 在 palladium diacetate 、 三苯基膦 、 三乙胺 、 甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.16h， 以72%的产率得到4-methyl-6-(4-methoxyphenyl)-2H-pyran-2-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

• Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors
  作者：Xu Dong、Li Chen、Zhitong Zheng、Xu Ma、Zaigang Luo、Liming Zhang

  DOI：10.1039/c8cc02494d

  日期：——

  A silver-catalyzed glycosylation reaction employing readily accessible and stable glycosyl ynenoates is developed. This reaction is mostly high yielding and exhibits varying levels of stereoinversion at the anomeric position. Compared to established and versatile Yu's gold catalysis, this chemistry features the use of substantially cheaper AgNTf2.

  已开发出一种银催化的糖基化反应，该反应采用了易于获得且稳定的糖基炔诺酸酯。该反应大部分是高收率的，并且在异头位置显示出不同水平的立体转化。与已建立且用途广泛的Yu的金催化方法相比，该化学方法的特点是使用了便宜得多的AgNTf 2。
• SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives
  作者：Kohei Sekine、Yuta Sadamitsu、Tohru Yamada

  DOI：10.1021/acs.orglett.5b03023

  日期：2015.11.20

  C-C bond forming carboxylation, and cyclization: of trimethyl(2-rnethylenbut-3,7yl)silaile derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the:corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2:furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig-cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.
• Lohaus; Dittmar, Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 8 a, p. 1311 - 1316
  作者：Lohaus、Dittmar

  DOI：——

  日期：——
• 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.