4'-methoxy-2'-[(p-tolylsulfonyl)oxy]acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-methoxy-2'-[(p-tolylsulfonyl)oxy]acetophenone
• 英文别名: (2-Acetyl-5-methoxy-phenyl) 4-methylbenzenesulfonate；(2-acetyl-5-methoxyphenyl) 4-methylbenzenesulfonate
• 化学式: C₁₆H₁₆O₅S
• 分子量: 320.366
• InChiKey: JOOGLKLXPDEPDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-methoxy-2'-[(p-tolylsulfonyl)oxy]acetophenone 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 11.67h， 生成 C₁₈H₁₈F₃NO₅S
  参考文献：
  名称：

  三氟甲基化 β-酮重氮的分子内 Appel 反应使三氟甲基吡唑的组装成为可能

  摘要：

  报道了一种生成三氟甲基化 β-酮重氮化合物的方法及其在分子内 Appel 型反应中的应用。该反应的关键成功之处在于重氮物质作为 Appel 反应中的 N-亲核试剂。该反应在温和条件下进行，底物范围广，三氟甲基吡唑的产率≤94%。该方案代表了一种新型的Appel反应，也是氟重氮烷烃的一种新反应模式。

  DOI：

  10.1021/acs.orglett.2c00738
• 作为产物：
  描述：

  丹皮酚 、 对甲苯磺酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以99%的产率得到4'-methoxy-2'-[(p-tolylsulfonyl)oxy]acetophenone
  参考文献：
  名称：

  三氟甲基化 β-酮重氮的分子内 Appel 反应使三氟甲基吡唑的组装成为可能

  摘要：

  报道了一种生成三氟甲基化 β-酮重氮化合物的方法及其在分子内 Appel 型反应中的应用。该反应的关键成功之处在于重氮物质作为 Appel 反应中的 N-亲核试剂。该反应在温和条件下进行，底物范围广，三氟甲基吡唑的产率≤94%。该方案代表了一种新型的Appel反应，也是氟重氮烷烃的一种新反应模式。

  DOI：

  10.1021/acs.orglett.2c00738

文献信息

• Low-dose paeonol derivatives alleviate lipid accumulation
  作者：Kuan-Chuan Pao、Jin-Feng Zhao、Tzong-Shyuan Lee、Ying-Pei Huang、Chien-Chung Han、Lin-Chiang Sherlock Huang、Kou-Hung Wu、Ming-Hua Hsu

  DOI：10.1039/c4ra13986k

  日期：——

  Here, we present a series of novel paeonol derivatives that prevent lipid accumulation at lower doses.

  这里，我们展示了一系列新颖的肉草酚衍生物，可以在较低剂量下防止脂质积聚。
• Advanced generation of paeonol-phenylsufonyl derivatives as potential anti-HBV agents
  作者：Y. P. Huang、H. P. Shih、Y. C. Liang、H. H. Lin、M. C. Lin、C. W. Chen、T. J. Huang、Y. C. Kuo、C. C. Han、M. H. Hsu

  DOI：10.1039/c6ra06119b

  日期：——

  paeonol-phenylsulfonyl derivatives and found that the compound 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate (6f) had the most potent antiviral effect against HBV, with an IC50 value of 0.36 μM and a high selectivity index (SI; TC50/IC50) of 47.75. In this research, we modified compound 6f with a 2-aminothiazole scaffold and generated 13 novel paeonol derivatives by utilizing various benzoyl and acyl chlorides

  乙型肝炎病毒（HBV）感染会导致严重的肝脏疾病，开发可用于慢性乙型肝炎的有效药物仍然是全球消灭HBV的重要一步。最近，我们的小组设计了丹皮酚-苯磺酰基衍生物，发现化合物2-乙酰基-5-甲氧基苯基4-甲氧基苯磺酸酯（6f）对乙肝病毒具有最强的抗病毒作用，IC 50值为0.36μM，选择性指数高（ SI； TC 50 / IC 50）为47.75。在本研究中，我们对化合物6f进行了改性用2-氨基噻唑骨架，利用各种苯甲酰和酰氯生成了13种新颖的pa药衍生物。在这一新一代产品中，化合物2-（2-苯甲并噻唑-4-基）-5-甲氧基苯基4-甲氧基苯磺酸盐（8a）的最高SI值为59.14，超过了化合物6f和拉米夫定（3TC）（可商购的抗病毒药物）的最高SI值。药品。因此，我们相信我们的研究可能为抗病毒药物的开发提供一些有用的信息。
• Synthesis, anti-oomycete activity, and SAR studies of paeonol derivatives
  作者：Yue-E Tian、Di Sun、Xiao-Xiao Han、Jin-Ming Yang、Song Zhang、Nan-Nan Feng、Li-Na Zhu、Zhong-Yuan Xu、Zhi-Ping Che、Sheng-Ming Liu、Xiao-Min Lin、Jia Jiang、Gen-Qiang Chen

  DOI：10.1080/10286020.2020.1718116

  日期：2021.2.1

  Three series of sulfonate derivatives of paeonol were synthesized and screened in vitro for their anti-oomycete activity against P. capsici, respectively. Among all the compounds, 4m displayed the best promising and pronounced anti-oomycete activity against P. capsici than zoxamide, with the EC50 values of 24.51 and 26.87 mg/L, respectively. The results show that acetyl and 4-OCH3 are two necessary groups. The existence of these two sites is closely related to the anti-oomycete activity. Relatively speaking, hydroxyl group is well tolerated, and the results showed that after modification of hydroxyl group with sulfonyl, the anti-oomycete activity was significantly increased.[GRAPHICS].
• Design, synthesis, and bioevaluation of paeonol derivatives as potential anti-HBV agents
  作者：Tsurng-Juhn Huang、Hong Chuang、Yu-Chuan Liang、Hui-Hsien Lin、Jia-Cherng Horng、Yu-Cheng Kuo、Chia-Wen Chen、Fu-Yuan Tsai、Shih-Chieh Yen、Shih-Ching Chou、Ming-Hua Hsu

  DOI：10.1016/j.ejmech.2014.11.050

  日期：2015.1

  Hepatitis B virus (HBV) is a causative reagent that frequently causes progressive liver diseases, leading to the development of acute, chronic hepatitis, cirrhosis, and eventually hepatocellular carcinoma (HCC). Despite several antiviral drugs including interferon-alpha and nucleotide derivatives are approved for clinical treatment for HBV, critical issues remain unresolved, e.g., low-to-moderate efficacy, adverse side effects, and resistant strains. In this study, novel Paeonol-phenylsulfonyl derivatives were synthesized and their antiviral effect against HBV was evaluated. The experimental results indicated that these compounds process significant antiviral potential, including the inhibition of viral antigen expression and secretion, and the suppression of HBV viral DNA replication. Among compounds synthesized in this research, compound 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate (7f) had the most potent inhibitory activity with IC50 value of 0.36 mu M, and high selectivity index, SI (TC50/IC50) 47.75; which exhibited an apparent inhibition effect on viral gene expression and viral propagation in cell culture model. So, we believe our compounds could serve as reservoir for antiviral drug development. (C) 2014 Elsevier Masson SAS. All rights reserved.