4-methyl-6-propyl-2H-pyran-2-one | 4472-67-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-methyl-6-propyl-2H-pyran-2-one
• 英文别名: 4-Methyl-6-propylpyran-2-one；4-methyl-6-propylpyran-2-one
• CAS: 4472-67-7
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: JKHBIBVVMPGLNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-6-propyl-2H-pyran-2-one 在 tetraphosphorus decasulfide 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以60%的产率得到4-methyl-6-propyl-2H-pyran-2-thione
  参考文献：
  名称：

  Development of Novel N-hydroxypyridone Derivatives as Potential Anti-Ischemic Stroke Agents

  摘要：

  Our previous study had identified ciclopirox (CPX) as a promising lead compound for treatment of ischemic stroke. To find better neuroprotective agents, a series of N-hydroxypyridone derivatives based on CPX were designed, synthesized, and evaluated in this study. Among these derivatives, compound 11 exhibits significant neuroprotection against oxygen glucose deprivation and oxidative stress -induced injuries in neuronal cells. Moreover, compound 11 possesses good blood-brain barrier permeability and superior antioxidant capability. In addition, a complex of compound 11 with olamine-11.01a possesses good water solubility, negligible hERG inhibition, and superior metabolic stability. The in vivo experiment demonstrates that 11.01a significantly reduces brain infarction and alleviates neurological deficits in middle cerebral artery occlusion rats. Hence, compound 11.01a is identified in our research as a prospective prototype in the innovation of stroke treatment.

  DOI：

  10.1021/acs.jmedchem.9b01338
• 作为产物：
  描述：

  3,3-二甲基丙烯酸甲酯 在 三氯化铝 、 硫酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 4-methyl-6-propyl-2H-pyran-2-one
  参考文献：
  名称：

  Antifungal Activity of 4-Methyl-6-alkyl-2H-pyran-2-ones

  摘要：

  A number of 4-methyl-6-alkyl-alpha-pyrones were synthesized and characterized on the basis of H-1 NMR and mass spectroscopy. These compounds were tested in vitro against pathogenic fungi, namely, Sclerotium rolfsii Saccardo, Rhizoctonia bataticola (Taub.) Butler, Pythium aphanidermatum (Edson) Fitz., Macrophomina phaseolina (Tassi), Pythium debaryanum (Hesse), and Rhizoctonia solani Nees. Lower homologues were less effective, whereas compounds such as 4-methyl-6-butyl-alpha-pyrone, 4-methyl-6-pentyl-alpha-pyrone, 4-methyl-6-hexyl-alpha-pyrone, and 4-methyl-6-heptyl-alpha-pyrone were found effective against all of the test fungi. They inhibited mycelial growth by approximately 50% (ED50) at 15-50 mu g/mL. 4-Methyl-6-hexyl-alpha-pyrone, which was found most effective, was tested against S. rolfsii in a greenhouse at 1, 5, and 10% concentrations. The 10% aqueous emulsion of 4-methyl-6-hexyl-alpha-pyrone suppressed disease development in tomato by 90-93% as compared with the untreated infested soil in the greenhouse after 35 days of treatment.

  DOI：

  10.1021/jf052792s

文献信息

• Synthesis and Biological Evaluations of Granulatamide B and its Structural Analogues
  作者：Dario Matulja、Petra Grbčić、Gabrijela Matijević、Sanja Babić、Krunoslav Bojanić、Sylvain Laclef、Valerije Vrček、Rozelindra Čož-Rakovac、Sandra Kraljević Pavelić、Dean Marković

  DOI：10.2174/0109298673272687231226111132

  日期：2024.2.12

  Background: While granulatamides A and B have been previously isolated, their biological activities have been only partially examined. The aim of this study was to synthesize granulatamide B (4b), a tryptamine-derivative naturally occurring in Eunicella coral species, using the well-known procedure of Sun and Fürstner and its 12 structural analogues by modifying the side chain, which differs in length, degree

  背景：虽然颗粒酰胺 A 和 B 之前已被分离出来，但它们的生物活性仅得到部分研究。本研究的目的是使用 Sun 和 Fürstner 的众所周知的程序，通过修饰长度不同的侧链来合成颗粒酰胺 B (4b)，这是一种天然存在于 Eunicella 珊瑚物种中的色胺衍生物。 、饱和度以及双键的数量和共轭。方法：除了使用斑马鱼模型进行体内毒性评估外，还对所制备的化合物库进行了生物活性的综合评估，包括抗氧化、抗增殖和抗菌特性。化合物 4i 由视黄酸部分组成，对 ABTS 自由基表现出最强的清除活性（IC50 = 36 ± 2 μM）。此外，4b 和一些类似物（4a、4c 和 4i）主要含有不饱和链和共轭双键，表现出中等但非选择性的活性，某些 IC50 值在 20-40 μM 范围内。结果：相比之下，类似物4l（α-亚麻酸的衍生物）对正常细胞系的毒性最小。此外，4b 对革兰氏阳性枯草芽孢杆菌也具有高度活性，MIC
• Antifungal Activity of 4-Methyl-6-alkyl-2H-pyran-2-ones
  作者：Tarun Kumar Chattapadhyay、Prem Dureja

  DOI：10.1021/jf052792s

  日期：2006.3.1

  A number of 4-methyl-6-alkyl-alpha-pyrones were synthesized and characterized on the basis of H-1 NMR and mass spectroscopy. These compounds were tested in vitro against pathogenic fungi, namely, Sclerotium rolfsii Saccardo, Rhizoctonia bataticola (Taub.) Butler, Pythium aphanidermatum (Edson) Fitz., Macrophomina phaseolina (Tassi), Pythium debaryanum (Hesse), and Rhizoctonia solani Nees. Lower homologues were less effective, whereas compounds such as 4-methyl-6-butyl-alpha-pyrone, 4-methyl-6-pentyl-alpha-pyrone, 4-methyl-6-hexyl-alpha-pyrone, and 4-methyl-6-heptyl-alpha-pyrone were found effective against all of the test fungi. They inhibited mycelial growth by approximately 50% (ED50) at 15-50 mu g/mL. 4-Methyl-6-hexyl-alpha-pyrone, which was found most effective, was tested against S. rolfsii in a greenhouse at 1, 5, and 10% concentrations. The 10% aqueous emulsion of 4-methyl-6-hexyl-alpha-pyrone suppressed disease development in tomato by 90-93% as compared with the untreated infested soil in the greenhouse after 35 days of treatment.
• Preparation and Decarboxylation of C-Acylated β-Methylglutaconic Anhydrides¹
  作者：Richard H. Wiley、Newton R. Smith

  DOI：10.1021/ja01135a054

  日期：1952.8
• Development of Novel <i>N</i>-hydroxypyridone Derivatives as Potential Anti-Ischemic Stroke Agents
  作者：Linghao Hu、Hongxuan Feng、Hongguang Zhang、Songda Yu、Qinyuan Zhao、Wei Wang、Fengxia Bao、Xun Ding、Jiajing Hu、Manjiong Wang、Yixiang Xu、Zengrui Wu、Xiaokang Li、Yun Tang、Fei Mao、Xiaoyan Chen、Haiyan Zhang、Jian Li

  DOI：10.1021/acs.jmedchem.9b01338

  日期：2020.2.13

  Our previous study had identified ciclopirox (CPX) as a promising lead compound for treatment of ischemic stroke. To find better neuroprotective agents, a series of N-hydroxypyridone derivatives based on CPX were designed, synthesized, and evaluated in this study. Among these derivatives, compound 11 exhibits significant neuroprotection against oxygen glucose deprivation and oxidative stress -induced injuries in neuronal cells. Moreover, compound 11 possesses good blood-brain barrier permeability and superior antioxidant capability. In addition, a complex of compound 11 with olamine-11.01a possesses good water solubility, negligible hERG inhibition, and superior metabolic stability. The in vivo experiment demonstrates that 11.01a significantly reduces brain infarction and alleviates neurological deficits in middle cerebral artery occlusion rats. Hence, compound 11.01a is identified in our research as a prospective prototype in the innovation of stroke treatment.