6-(4-Methylphenyl)-4-methylsulfanyl-2-oxopyran-3-carboxylic acid | 127449-57-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-(4-Methylphenyl)-4-methylsulfanyl-2-oxopyran-3-carboxylic acid
• CAS: 127449-57-4
• 化学式: C₁₄H₁₂O₄S
• 分子量: 276.313
• InChiKey: GXRJCKQSZCHIPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-Methylphenyl)-4-methylsulfanyl-2-oxopyran-3-carboxylic acid 在 sodium hydride 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-cyclopropyl-4-(methylthio)-2-oxo-6-(p-tolyl)-1,2-dihydropyridine-3-carboxylic acid
  参考文献：
  名称：

  酰胺基离子介导的 2-吡喃酮分子内环转化为 2-吡啶酮

  摘要：

  在此，我们报告了一种新的且具有成本效益的方法，用于从2-吡喃酮-3-甲酰胺 ( 1 ) 合成N-取代的2-吡啶酮-3-羧酸 ( 2 )，在室温下具有良好的产率。该反应的显着特点是促进 NaH 介导的酰胺离子形成，从而引发分子内环转化。除了环化之外，还实现了在无金属条件下一锅同时脱羧和取代，从1得到N-取代的2-吡啶酮( 3 ) 。

  DOI：

  10.1002/jhet.4671
• 作为产物：
  描述：

  1-(4-甲基苯基)-3,3-二(甲硫基)-2-丙烯-1-酮 、 丙二酸二乙酯 在 sodium hydride 作用下， 生成 6-(4-Methylphenyl)-4-methylsulfanyl-2-oxopyran-3-carboxylic acid
  参考文献：
  名称：

  酰胺基离子介导的 2-吡喃酮分子内环转化为 2-吡啶酮

  摘要：

  在此，我们报告了一种新的且具有成本效益的方法，用于从2-吡喃酮-3-甲酰胺 ( 1 ) 合成N-取代的2-吡啶酮-3-羧酸 ( 2 )，在室温下具有良好的产率。该反应的显着特点是促进 NaH 介导的酰胺离子形成，从而引发分子内环转化。除了环化之外，还实现了在无金属条件下一锅同时脱羧和取代，从1得到N-取代的2-吡啶酮( 3 ) 。

  DOI：

  10.1002/jhet.4671

文献信息

• Anti-HSV activity and mode of action study of α-pyrone carboxamides
  作者：Srinivas Karampuri、Durbadal Ojha、Paromita Bag、Harapriya Chakravarty、Chandralata Bal、Debprasad Chattopadhyay、Ashoke Sharon

  DOI：10.1039/c4ra01303d

  日期：——

  Potential anti-HSV lead candidate3d(EC₅₀= 9.8 μg ml⁻¹) and its possible binding mode to utilize cavity-A and cavity-B of viral enzyme HSV polymerase.

  潜在的抗HSV首选候选药物3d（EC50= 9.8 μg ml-1）及其可能的结合模式，利用病毒酶HSV聚合酶的空腔A和空腔B。
• <scp>Microwave‐assisted</scp> decarboxylation of <scp> 2 <i>H</i> ‐Pyran‐3‐carboxylic </scp> acid derivatives under basic condition
  作者：Uttam Kumar Mishra、Chandralata Bal

  DOI：10.1002/jhet.4559

  日期：2022.12

  Despite the availability of several methods for decarboxylation, this area remains exploratory and requires new development. Here, we report a highly efficient microwave-assisted hydrodecarboxylation of 4-(methylthio)-2-oxo-6-aryl-2H-pyran-3-carboxylic acids (1a-k) under basic condition to obtain 4-(methylthio)-6-aryl-2H-pyran-2-ones (2a-k) with >90% yield. The requirement of proton source from the

  尽管有多种脱羧方法可用，但该领域仍处于探索阶段，需要新的发展。在这里，我们报道了在碱性条件下 4-(甲硫基)-2-氧代-6-芳基-2 H-吡喃-3-羧酸 ( 1a-k ) 的高效微波辅助加氢脱羧反应，得到 4-(甲硫基) -6-aryl-2 H -pyran-2-ones ( 2a-k ) 产率 >90%。通过在CD 3 OD中进行1b和1e的反应，分别获得氘代化合物2 l和2 m，观察到溶剂对质子源的需求。所有化合物均通过光谱分析进行了表征。此外，化合物通过单晶 X 射线衍射研究分析了2b和2e 。
• Synthesis and anti-HCV determinant motif identification in pyranone carboxamide scaffold
  作者：Tuniki Balaraju、Ananda Kumar Konreddy、Afsana Parveen、Massaki Toyama、Wataru Ito、Srinivas Karampuri、Masanori Baba、Ashoke Sharon、Chandralata Bal

  DOI：10.1016/j.bmcl.2015.09.060

  日期：2015.11

  Hepatitis C Virus exhibits high genetic diversity. The current treatment for genotype-1 with similar to 80% sustained virologic responses is a combination of pegylated interferon, ribavirin and boceprevir/telaprevir/simeprevir which is associated with several side effects and need close monitoring. Therefore, novel therapies are invited for safer and more efficient treatment. This study was designed for synthesis of new alpha-pyranone carboxamide analogs for evaluation of anti-HCV activity to delineate structure-activity relationship (SAR) and to identify anti-HCV determinant motif on this new scaffold. Forty four new alpha-pyranone carboxamide analogs were synthesized. Six potential anti-HCV candidates 11a (EC50 = 0.35 mu M), 11e (EC50 = 0.48 mu M), 12f (EC50 = 0.47 mu M), 12g (EC50 = 0.39 mu M), 12h (EC50 = 0.20 mu M) and 12j (EC50 = 0.25 mu M) with lower cytotoxicity (CC50 > 20 mu M) were discovered through cell based HCV replicon system. The activity profile of forty four new a-pyranone carboxamide analogs suggests the role of an aromatic motif in the B region to add a synergistic effect to NHOH motif at 4-position and revels an anti-HCV activity determinants motif under this scaffold. The biochemical assay against most promising HCV target protein 'NS3 protease and NS5B polymerase' showed no activity and open a scope to explore new mechanism inhibitor. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and Anti-HCV Activity of 4-Hydroxyamino α-Pyranone Carboxamide Analogues
  作者：Ananda Kumar Konreddy、Massaki Toyama、Wataru Ito、Chandralata Bal、Masanori Baba、Ashoke Sharon

  DOI：10.1021/ml400432f

  日期：2014.3.13

  High genetic variability in hepatitis C virus (HCV), emergence of drug resistant viruses and side effects demand the requirement for development of new scaffolds to show an alternate mechanism. Herein, we report discovery of new scaffold I based on 4-hydroxyamino alpha-pyranone carboxamide as promising anti-HCV agents. A comprehensive structure activity relationship (SAR) was explored with several newly synthesized compounds. In all promising compounds (17-19, 21-22, 24-25, and 49) with EC50 ranging 0.15 to 0.40 mu M, the aryl group at C-6 position of alpha-pyranone were unsubstituted. In particular, 25 demonstrated potential anti-HCV activity with EC50 of 0.18 mu M in cell based HCV replicon system with lower cytotoxicity (CC50 > 20 mu M) and provided a new scaffold for anti-HCV drug development. Further investigations, including biochemical characterization, are yet to be performed to elucidate its possible mode of action.