4-hydroxy-6-methyl-3-phenylpyridin-2(1H)-one | 24555-55-3

• 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: 4-hydroxy-6-methyl-3-phenylpyridin-2(1H)-one
• 英文别名: 4-hydroxy-6-methyl-3-phenyl-1H-pyridin-2-one
• CAS: 24555-55-3
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: PNJGEMBXMCQISU-UHFFFAOYSA-N

物化性质

• 沸点：
  410.7±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-methyl-3-phenylpyridin-2(1H)-one 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 16.33h， 生成 6-methyl-3-phenyl-4-trifluoroacetylamino-pyridin-2(1H)-one
  参考文献：
  名称：

  Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2 (1H)-ones

  摘要：

  4-Hydroxy-3-phenylpyridin-2 (1H)-ones with different substituents either at N-1 or in the phenyl group were synthesized by reaction of ethyl-beta-aminocrotonates with dialkyl malonates or 'magic malonates' (2,4,6-trichlorophenyl malonates). The evaluation of these compounds on Mycobacterium tuberculosis H37Ra, Escherichia coli B and Staphylococcus aureus ATCC 25923 showed significant inhibitory effects on M tuberculosis (5g and 5s, MIC = 8-mu-g/ml). A structure-activity relationship is discussed.

  DOI：

  10.1016/0223-5234(91)90194-r
• 作为产物：
  描述：

  苯基丙二酸二乙酯 在 sodium hydroxide 作用下， 反应 2.5h， 生成 4-hydroxy-6-methyl-3-phenylpyridin-2(1H)-one
  参考文献：
  名称：

  Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2 (1H)-ones

  摘要：

  4-Hydroxy-3-phenylpyridin-2 (1H)-ones with different substituents either at N-1 or in the phenyl group were synthesized by reaction of ethyl-beta-aminocrotonates with dialkyl malonates or 'magic malonates' (2,4,6-trichlorophenyl malonates). The evaluation of these compounds on Mycobacterium tuberculosis H37Ra, Escherichia coli B and Staphylococcus aureus ATCC 25923 showed significant inhibitory effects on M tuberculosis (5g and 5s, MIC = 8-mu-g/ml). A structure-activity relationship is discussed.

  DOI：

  10.1016/0223-5234(91)90194-r

文献信息

• Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy
  作者：Mingxuan Liang、Mengling He、Zhiqing Zhong、Bei Wan、Qingfeng Du、Shaoyu Mai

  DOI：10.1002/anie.202400741

  日期：2024.4.22

  A general and catalytic α-arylation of cyclic 1,3-dicarbonyls have been developed, providing expedient access toward a wide range of high-value 2-aryl (hetero)cyclic 1,3-dicarbonyls. The key to success is through a cyclic iodonium ylide strategy. Our approach is base-free and exhibits broad substrate scope (>100 examples). Importantly, our approach allows late-stage modification and significantly simplifying

  环状 1,3-二羰基的通用催化 α-芳基化已经开发出来，为获得各种高价值的 2-芳基（杂）环 1,3-二羰基提供了便利。成功的关键是通过环状碘叶立德策略。我们的方法是无碱基的，并且具有广泛的底物范围（> 100 个示例）。重要的是，我们的方法允许后期修改并显着简化先前的合成。
• Structure activity relationships of 4-hydroxy-2-pyridones: A novel class of antituberculosis agents
  作者：Pearly Shuyi Ng、Ujjini H. Manjunatha、Srinivasa P.S. Rao、Luis R. Camacho、Ngai Ling Ma、Maxime Herve、Christian G. Noble、Anne Goh、Stefan Peukert、Thierry T. Diagana、Paul W. Smith、Ravinder Reddy Kondreddi

  DOI：10.1016/j.ejmech.2015.10.008

  日期：2015.12

  Pyridone 1 was identified from a high-throughput cell-based phenotypic screen against Mycobacterium tuberculosis (Mtb) including multi-drug resistant tuberculosis (MDR-TB) as a novel anti-TB agent and subsequently optimized series using cell-based Mtb assay. Preliminary structure activity relationship on the isobutyl group with higher cycloalkyl groups at 6-position of pyridone ring has enabled us to significant improvement of potency against Mtb. The lead compound 30j, a dimethylcyclohexyl group on the 6-position of the pyridone, displayed desirable in vitro potency against both drug sensitive and multi-drug resistant TB clinical isolates. In addition, 30j displayed favorable oral pharmacokinetic properties and demonstrated in vivo efficacy in mouse model. These results emphasize the importance of 4-hydroxy-2-pyridones as a new chemotype and further optimization of properties to treat MDR-TB. (C) 2015 Elsevier Masson SAS. All rights reserved.