4'-methoxy-2'-[(4-methoxyphenylsulfonyl)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'-[(4-methoxyphenylsulfonyl)oxy]acetophenone
• 英文别名: 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate；(2-Acetyl-5-methoxy-phenyl) 4-methoxybenzenesulfonate；(2-acetyl-5-methoxyphenyl) 4-methoxybenzenesulfonate
• 化学式: C₁₆H₁₆O₆S
• 分子量: 336.365
• InChiKey: IVFXIUZACQEROT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4'-methoxy-2'-[(4-methoxyphenylsulfonyl)oxy]acetophenone 在 碘 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 5-methoxy-2-(2-(4-methylbenzamido)thiazol-4-yl)phenyl 4-methoxybenzenesulfonate
  参考文献：
  名称：

  新一代的丹皮酚-苯磺酰衍生物可作为潜在的抗乙肝病毒药物†

  摘要：

  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。

  DOI：

  10.1039/c6ra06119b
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 4'-methoxy-2'-[(4-methoxyphenylsulfonyl)oxy]acetophenone
  参考文献：
  名称：

  2-羟基-4-(羟基/甲氧基)苯乙酮衍生的氟化磺酸酯作为与 2 型糖尿病相关的生化靶点抑制剂的结构和生物学性质研究

  摘要：

  氟原子或含氟基团取代的小分子多靶点药物因其在治疗多因素疾病方面的优势而继续引起药物化学的广泛关注。在这项研究中，含氟烷基和苯磺酰氯结构单元与2,4-二羟基苯乙酮1a或2-羟基-4-甲氧基苯乙酮1b反应，分别得到相应的磺酸酯衍生物2a – f和2g – j。对每个系列的代表性化合物进行了详细的晶体学表征。通过体外酶测定评估了这些化合物抑制与 2 型糖尿病相关的生化靶标的潜力。化合物1a及其4-(4-氟苯基)磺酰基衍生物2d在体外对α-葡萄糖苷酶(IC 50  = 0.97 ± 0.02 μM和0.81 ± 0.07 μM)和α-淀粉酶(IC 50  =与阿卡波糖相比（IC 50 分别为 6.89 ± 0.04 μM 和 4.87 ± 0.02 μM）（IC 50 分别为 8.60 ± 0.20 μM 和 1.96 ± 0.03 μM）。与 PTP1B 抑制剂苏拉明(IC 50 = 4.63 ±

  DOI：

  10.1016/j.jfluchem.2023.110233

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。
• 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.