(E)-3-(3,4-bis(benzyloxy)phenyl)-1-(4-hydroxybenzofuran-5-yl)prop-2-en-1-one | 1279111-35-1

• 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-(4-hydroxybenzofuran-5-yl)prop-2-en-1-one
• CAS: 1279111-35-1
• 化学式: C₃₁H₂₄O₅
• 分子量: 476.529
• InChiKey: PJFVLVWFIIJEJJ-SDNWHVSQSA-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-(4-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68%的产率得到(E)-3-(3,4-dihydroxyphenyl)-1-(4-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：

  3,4-二苄氧基苯甲醛 、 1-(4-羟基-1-苯并呋喃-5-基)乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以75%的产率得到(E)-3-(3,4-bis(benzyloxy)phenyl)-1-(4-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