(E)-3-(3,4-bis(benzyloxy)phenyl)-1-(6-hydroxybenzofuran-5-yl)prop-2-en-1-one | 913615-96-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(3,4-bis(benzyloxy)phenyl)-1-(6-hydroxybenzofuran-5-yl)prop-2-en-1-one
• CAS: 913615-96-0
• 化学式: C₃₁H₂₄O₅
• 分子量: 476.529
• InChiKey: YODYHOCORGIWEO-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.9
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(3,4-bis(benzyloxy)phenyl)-1-(6-hydroxybenzofuran-5-yl)prop-2-en-1-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以54%的产率得到(E)-3-(3,4-dihydroxyphenyl)-1-(6-hydroxybenzofuran-5-yl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of antihyperglycemic, α-glucosidase inhibitory, and DPPH free radical scavenging furanochalcones

  摘要：

  A series of furanochalcone derivatives have been designed and synthesized. Molecular modeling studies were carried out to probe into the mechanism of binding of chalcone inhibitors and understand the structure-activity relationship to identify the contribution of scaffolds and groups in the synthesized analogs to biological activity. The three-dimensional model of alpha-glucosidase was constructed based on the crystal structure family 31 alpha-glycosidase (PDB 1XSI) using Modeller9v5. Docking of the inhibitors on the built homology model revealed interactions in the active site region mostly with Asp 252, Tyr254, Gln523, and Arg571. 2D-QSAR models were generated with CODESSA using Heuristic method. The best predictive model was generated using three descriptors that gave a correlation co-efficient (r (2)) 0.9886 and cross-validate (r (2)) 0.9338. The synthesized compounds were screened against the alpha-glucosidase inhibition and DPPH radical scavenging properties. All the synthetic compounds displayed varying degrees of alpha-glucosidase inhibitory and DPPH scavenging activities. Compound 8c was found most potent alpha-glucosidase inhibitor though; it could not display DPPH scavenging activity. When tested in vivo for antihyperglycemic activity in starch-loaded Wistar rats, 8c was equally effective in reducing time-dependent hyperglycemia as to the standard drug, Acarbose. Compound 8c may serve as an interesting compound for the development of therapeutics targeted against diet-induced hyperglycemia in diabetes.

  DOI：

  10.1007/s00044-011-9583-7
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 氢氧化钾 、 Amberlyst 15 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (E)-3-(3,4-bis(benzyloxy)phenyl)-1-(6-hydroxybenzofuran-5-yl)prop-2-en-1-one
  参考文献：
  名称：

  Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L.

  摘要：

  Two new furanoflavonoids (1, 2), one new chalcone dimer (3) along with six known compounds, chrysophanol, 5-O-methyl squarrosin, 5-methoxy furano[4",5",6,7]flavone, calodenone, lophirone A and lophirone H were isolated from the ethyl acetate-soluble fraction of methanol extract of root bark of Ochna squarrosa. Chrysophanol, calodenone, lophirone A and lophirone H were isolated from this plant for the first time. The structures of all the isolated compounds were confirmed by 1D and 2D spectroscopic data. These compounds were tested for analgesic and anti-inflammatory activity. All the new compounds showed good analgesic and anti-inflammatory activity. A simple and facile method for the cleavage of benzyl ethers using I-2 in trigol is also reported. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.048