3-hydroxy-7-methoxy-2-p-tolyl-4H-chromen-4-one | 93175-99-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-hydroxy-7-methoxy-2-p-tolyl-4H-chromen-4-one
• 英文别名: 3-Hydroxy-7-methoxy-2-(4-methylphenyl)-4H-1-benzopyran-4-one；3-hydroxy-7-methoxy-2-(4-methylphenyl)chromen-4-one
• CAS: 93175-99-6
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: WHTTVCYTRJNKSL-UHFFFAOYSA-N

物化性质

• 沸点：
  457.3±45.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-7-methoxy-2-p-tolyl-4H-chromen-4-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 11.0h， 生成 3-(3-(benzo[d]oxazol-2-ylthio)propoxy)-7-methoxy-2-(4-tolyl)-4H-chromen-4-one
  参考文献：
  名称：

  含有苯并恶唑作为潜在抗病毒剂的新型黄酮醇衍生物：设计、合成和生物学评价

  摘要：

  设计合成了一系列含有苯并恶唑的黄酮醇衍生物，并通过核磁共振 （NMR） 和高分辨率质谱 （HRMS） 确定了所有目标化合物的结构。通过单晶 X 射线衍射分析进一步证实了 X2 的结构。生物活性测试结果表明，一些目标化合物在体内对烟草花叶病毒 （TMV） 具有优异的抗病毒活性。特别是，X17 对 TMV 的疗效和保护活性的中位有效浓度 （EC50） 值分别为 127.6 和 101.2 μg/mL，优于宁南霉素 （320.0 和 234.6 μg/mL）。初步机制研究结果表明，X17 对 TMV 外壳蛋白 （TMV-CP） 具有很强的结合亲和力，这可能会阻碍 TMV 颗粒的自组装和复制。此外，X17 能够有效抑制烟叶膜脂质过氧化，促进 O2− 从体内清除，从而提高烟草植株的抗病性。因此，含有苯并噁唑的黄酮醇衍生物的设计合成为新型抗病毒药物的开发提供了价值。  图形摘要

  DOI：

  10.1007/s11030-023-10786-5
• 作为产物：
  描述：

  (E)-1-(2-hydroxy-4-methoxyphenyl)-3-p-tolylprop-2-en-1-one 在 双氧水 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以43%的产率得到3-hydroxy-7-methoxy-2-p-tolyl-4H-chromen-4-one
  参考文献：
  名称：

  Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation

  摘要：

  The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.

  DOI：

  10.1016/j.bmcl.2014.06.061

文献信息

• Rao, Takkellapati Sudhakar; Trivedi, Girish Kumar, Heterocycles, 1987, vol. 26, # 8, p. 2117 - 2124
  作者：Rao, Takkellapati Sudhakar、Trivedi, Girish Kumar

  DOI：——

  日期：——
• Rao, Takkellapati Sudhakar; Deshpande, Shubhada; Mathur, Hari Har, Heterocycles, 1984, vol. 22, # 9, p. 1943 - 1946
  作者：Rao, Takkellapati Sudhakar、Deshpande, Shubhada、Mathur, Hari Har、Irivedi, Girish Kumar

  DOI：——

  日期：——
• RAO, TAKKELLAPATI, SUDHAKAR;DESHPANDE, SHUBHADA;MATHUR, HARI, HAR;TRIVEDI+, HETEROCYCLES, 1984, 22, N 9, 1943-1946
  作者：RAO, TAKKELLAPATI, SUDHAKAR、DESHPANDE, SHUBHADA、MATHUR, HARI, HAR、TRIVEDI+

  DOI：——

  日期：——
• Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
  作者：Kamal Rullah、Mohd Fadhlizil Fasihi Mohd Aluwi、Bohari M. Yamin、Mohd Nazri Abdul Bahari、Leong Sze Wei、Syahida Ahmad、Faridah Abas、Nor Hadiani Ismail、Ibrahim Jantan、Lam Kok Wai

  DOI：10.1016/j.bmcl.2014.06.061

  日期：2014.8

  The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.
• Novel flavonol derivatives containing benzoxazole as potential antiviral agents: design, synthesis, and biological evaluation
  作者：Yuanxiang Zhou、Zhiling Sun、Qing Zhou、Wei Zeng、Miaohe Zhang、Shuang Feng、Wei Xue

  DOI：10.1007/s11030-023-10786-5

  日期：——

  synthesized, and the structures of all the target compounds were determined by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). The structure of X2 was further confirmed by single crystal X-ray diffraction analysis. The results of the bioactivity tests showed that some of the target compounds possessed excellent antiviral activity against tobacco mosaic virus (TMV) in

  设计合成了一系列含有苯并恶唑的黄酮醇衍生物，并通过核磁共振 （NMR） 和高分辨率质谱 （HRMS） 确定了所有目标化合物的结构。通过单晶 X 射线衍射分析进一步证实了 X2 的结构。生物活性测试结果表明，一些目标化合物在体内对烟草花叶病毒 （TMV） 具有优异的抗病毒活性。特别是，X17 对 TMV 的疗效和保护活性的中位有效浓度 （EC50） 值分别为 127.6 和 101.2 μg/mL，优于宁南霉素 （320.0 和 234.6 μg/mL）。初步机制研究结果表明，X17 对 TMV 外壳蛋白 （TMV-CP） 具有很强的结合亲和力，这可能会阻碍 TMV 颗粒的自组装和复制。此外，X17 能够有效抑制烟叶膜脂质过氧化，促进 O2− 从体内清除，从而提高烟草植株的抗病性。因此，含有苯并噁唑的黄酮醇衍生物的设计合成为新型抗病毒药物的开发提供了价值。  图形摘要