3,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

• 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: 3,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
• 英文别名: 3,6-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one；3,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: OWIZIWOEDNQOKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二羟基苯乙酮 在 茴香硫醚 、 双氧水 、 三氟乙酸 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 8.0h， 生成 3,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction

  摘要：

  Chrysosplenol C (4',5,6-trihydroxy-3,3',7-tri-methoxyflavone) isolated from Miliusa balansae has unique structural features as a reversible inotropic agent independent of beta-adrenergic signaling and with selective activation of cardiac myosin ATPase. Hence, a series of chrysosplenol analogues were synthesized and explored for identification of pharmacophore that is essential for the increasing contractility in rat ventricular myocytes. Analogue 7-chloro-2-(3-hydroxypheny1)-3-methoxy-4H-chromen-4-one showed highly potent contractility (54.8% at 10 mu M) through activating cardiac myosin ATPase (38.7% at 10 mu M). Our systematic structure activity relationship study revealed that flavonoid nucleus of chrososplenol C appears to be an essential basic skeleton and hydrophobic substituent at position 7 of chromenone such as methoxy or chloro enhances the activity. Additionally, our ATPase study suggested that these chrysosplenol analogues have selectivity toward cardiac myosin activation. Thus, the novel flavonone with 3-/7-hydrophobic substituent and 3'-hydrogen bonding donor function is a novel scaffold for discovery of a new positive inotropic agent.

  DOI：

  10.1021/acsmedchemlett.5b00043

文献信息

• Green access to flavonols by one-pot serial aldol condensation/Algar–Flynn–Oyamada reaction catalyzed using the new bio-based catalyst of alkaline amylopectin
  作者：Fatemeh Tamaddon、Hossein Rashidi

  DOI：10.1007/s11164-023-05138-9

  日期：2023.12

  Herein, alkaline amylopectin (AAp) was prepared under chemo-mechanically dry conditions, characterized by base capacity, FT-IR, FESEM, TEM, and TGA analyses, and held as a new bio-organic base catalyst in the one-pot synthesis of flavonols. With a base capacity of 7.3 mmolHO−/g, AAp catalyzed initial aldol condensation and further Algar–Flynn–Oyamada reaction in cooperation with hydrogen peroxide to

  在此，在化学机械干燥条件下制备碱性支链淀粉（AAp），通过碱容量、FT-IR、FESEM、TEM 和 TGA 分析进行表征，并作为新型生物有机碱催化剂用于一锅合成黄酮醇。基本容量为 7.3 mmolH2O -/g，AAp 催化初始羟醛缩合，并与过氧化氢配合进一步进行 Algar-Flynn-Oyamada 反应，得到高产率的黄酮醇抗氧化剂。因此，原位形成的2'-羟基查耳酮的第一次羟醛缩合或随后的氧化环化/羟基化在锅中成功进行，形成黄酮醇产品，而没有橙酮副产物。发现超分子碱催化剂AAp在重复使用五次后结构得到了很好的保存。该方案的优点是反应物可用、无苯醌副产物、反应时间短、产率高和催化剂可重复使用。 图形概要
• Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction
  作者：Eeda Venkateswararao、Min-Jeong Son、Niti Sharma、Manoj Manickam、PullaReddy Boggu、Young Ho Kim、Sun-Hee Woo、Sang-Hun Jung

  DOI：10.1021/acsmedchemlett.5b00043

  日期：2015.7.9

  Chrysosplenol C (4',5,6-trihydroxy-3,3',7-tri-methoxyflavone) isolated from Miliusa balansae has unique structural features as a reversible inotropic agent independent of beta-adrenergic signaling and with selective activation of cardiac myosin ATPase. Hence, a series of chrysosplenol analogues were synthesized and explored for identification of pharmacophore that is essential for the increasing contractility in rat ventricular myocytes. Analogue 7-chloro-2-(3-hydroxypheny1)-3-methoxy-4H-chromen-4-one showed highly potent contractility (54.8% at 10 mu M) through activating cardiac myosin ATPase (38.7% at 10 mu M). Our systematic structure activity relationship study revealed that flavonoid nucleus of chrososplenol C appears to be an essential basic skeleton and hydrophobic substituent at position 7 of chromenone such as methoxy or chloro enhances the activity. Additionally, our ATPase study suggested that these chrysosplenol analogues have selectivity toward cardiac myosin activation. Thus, the novel flavonone with 3-/7-hydrophobic substituent and 3'-hydrogen bonding donor function is a novel scaffold for discovery of a new positive inotropic agent.