2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-furo[2,3-h]chromen-4-one | 1279111-47-5

• 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: 2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-furo[2,3-h]chromen-4-one
• 英文别名: 2-(3,4-Bis (benzyloxy)phenyl)-3-hydroxy-4h-furo[2,3-h]chromen-4-one；2-[3,4-bis(phenylmethoxy)phenyl]-3-hydroxyfuro[2,3-h]chromen-4-one
• CAS: 1279111-47-5
• 化学式: C₃₁H₂₂O₆
• 分子量: 490.512
• InChiKey: WHJXTFOXJCULNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-furo[2,3-h]chromen-4-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以64%的产率得到2-(3,4-dihydroxy-phenyl)-3-hydroxy-furo[2,3-h]chromen-4-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 在 双氧水 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 生成 2-(3,4-bis(benzyloxy)phenyl)-3-hydroxy-4H-furo[2,3-h]chromen-4-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

文献信息

• Synthesis of antihyperglycemic, α-glucosidase inhibitory, and DPPH free radical scavenging furanochalcones
  作者：R. Ranga Rao、Ashok K. Tiwari、P. Prabhakar Reddy、K. Suresh Babu、G. Suresh、A. Zehra Ali、K. Madhusudana、Sachin B. Agawane、Preethi Badrinarayan、G. Narahari Sastry、J. Madhusudana Rao

  DOI：10.1007/s00044-011-9583-7

  日期：2012.6

  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.