3-acetyl-8,8-dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one | 263903-39-5

• 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: 3-acetyl-8,8-dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one
• 英文别名: 3-Acetyl-8,8-dimethyl-7,8-dihydro-2h,6h-pyrano[3,2-g]chromen-2-one；7-acetyl-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• CAS: 263903-39-5
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: CQAYGRJNPLYJLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetyl-8,8-dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one 在 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 生成 diethyl 3-(8,8-dimethyl-2-oxo-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-3-yl)-1-(3-methylphenyl)-1H-4,5-pyrazoledicarboxylate
  参考文献：
  名称：

  Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates

  摘要：

  2-Oxo-2H-chromenylpyrazolecarboxylates (8a-h and 12a-zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a-h and 11a-w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H)-ones (13i-n) were prepared from corresponding phenylhydrazones (7a-h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100 degrees C. All the synthesized compounds (8a-h, 12a-zb and 13a-n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.042
• 作为产物：
  描述：

  2-甲基-3-丁烯-2-醇 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 3-acetyl-8,8-dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-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

• Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates
  作者：J. Ashok Kumar、G. Saidachary、G. Mallesham、B. Sridhar、Nishant Jain、Shashi Vardhan Kalivendi、V. Jayathirtha Rao、B. China Raju

  DOI：10.1016/j.ejmech.2013.03.042

  日期：2013.7

  2-Oxo-2H-chromenylpyrazolecarboxylates (8a-h and 12a-zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a-h and 11a-w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H)-ones (13i-n) were prepared from corresponding phenylhydrazones (7a-h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100 degrees C. All the synthesized compounds (8a-h, 12a-zb and 13a-n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 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.