7-Benzoyl-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one | 263903-41-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-Benzoyl-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• 英文别名: 7-benzoyl-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• CAS: 263903-41-9
• 化学式: C₂₁H₁₈O₄
• 分子量: 334.372
• InChiKey: LFQASVMDYLJJQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 哌啶 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 4.5h， 生成 7-Benzoyl-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
  参考文献：
  名称：

  Pancreatic α-amylase inhibition and free radical scavenging activity of substituted pyranochromenone derivatives

  摘要：

  Pyranochromenone derivatives 3a-d, 6a-j and 2H-chromenones 8a-b were synthesized and screened for their in vitro alpha-amylase inhibitory and ABTS(aEuro cent+) [2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)] free radical scavenging activities. Compounds 3a, 3c, and 6d displayed dual function of ABTS(aEuro cent+) radical scavenging as well as alpha-amylase inhibition. Compound 6h was found to be most potent alpha-amylase inhibitor in present series of compounds. Docking studies suggest that these compounds occupy active site of the human pancreatic alpha-amylase similar to that of acarbose which inhibits enzyme by hydrophobic interactions. These compounds have potential to be developed as therapeutics targeted against diet-induced hyperglycemia in diabetes.Series of pyranochromenone derivatives 3a-d, 6a-j, and 8a-b were synthesized, among these compound 6h shown potent intestinal alpha-amylase inhibitory activity. Compounds 3a, 3c, and 6d were shown dual properties such as alpha-amylase inhibitory and antioxidant activities. These derivatives may serve as a model compounds for design and development of therapeutics based agents.

  DOI：

  10.1007/s00044-013-0867-y

文献信息

• Pancreatic α-amylase inhibition and free radical scavenging activity of substituted pyranochromenone derivatives
  作者：J. Ashok Kumar、Ashok K. Tiwari、G. Saidachary、Chandan Kishor、D. Anand Kumar、Zehra Ali、B. Sridhar、Anthony Addlagatta、B. China Raju

  DOI：10.1007/s00044-013-0867-y

  日期：2014.6

  Pyranochromenone derivatives 3a-d, 6a-j and 2H-chromenones 8a-b were synthesized and screened for their in vitro alpha-amylase inhibitory and ABTS(aEuro cent+) [2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)] free radical scavenging activities. Compounds 3a, 3c, and 6d displayed dual function of ABTS(aEuro cent+) radical scavenging as well as alpha-amylase inhibition. Compound 6h was found to be most potent alpha-amylase inhibitor in present series of compounds. Docking studies suggest that these compounds occupy active site of the human pancreatic alpha-amylase similar to that of acarbose which inhibits enzyme by hydrophobic interactions. These compounds have potential to be developed as therapeutics targeted against diet-induced hyperglycemia in diabetes.Series of pyranochromenone derivatives 3a-d, 6a-j, and 8a-b were synthesized, among these compound 6h shown potent intestinal alpha-amylase inhibitory activity. Compounds 3a, 3c, and 6d were shown dual properties such as alpha-amylase inhibitory and antioxidant activities. These derivatives may serve as a model compounds for design and development of therapeutics based agents.