4'6'-dibenzyloxy-2'-hydroxychalcone | 120979-97-7

• 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: 4'6'-dibenzyloxy-2'-hydroxychalcone
• 英文别名: 2'-hydroxy-4',6'-di(benzyloxy)chalcone；(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-phenylprop-2-en-1-one；(E)-1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-phenylprop-2-en-1-one
• CAS: 120979-97-7
• 化学式: C₂₉H₂₄O₄
• 分子量: 436.507
• InChiKey: NORWNVXWVABTCI-WUKNDPDISA-N

物化性质

• 沸点：
  662.4±55.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'6'-dibenzyloxy-2'-hydroxychalcone 在 碘 、 二甲基亚砜 作用下， 以92%的产率得到5,7-di(benzyloxy)flavone
  参考文献：
  名称：

  Facile synthesis of norwogonin, isoscutellarein, and herbacetin

  摘要：

  An expeditious synthesis of norwogonin, isoscutellarein, and herbacetin, has been accomplished by a strategy featuring a borylation of sterically hindered aryl iodide and a one-pot oxidation to generate the C-3 and C-8 OH groups. The total synthesis gives excellent yields and conventional flash column chromatography is not needed for purification. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.06.085
• 作为产物：
  描述：

  2-乙酰基-3,5-双(苄氧基)苯酚 、 苯甲醛 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.83h， 以98%的产率得到4'6'-dibenzyloxy-2'-hydroxychalcone
  参考文献：
  名称：

  Facile synthesis of norwogonin, isoscutellarein, and herbacetin

  摘要：

  An expeditious synthesis of norwogonin, isoscutellarein, and herbacetin, has been accomplished by a strategy featuring a borylation of sterically hindered aryl iodide and a one-pot oxidation to generate the C-3 and C-8 OH groups. The total synthesis gives excellent yields and conventional flash column chromatography is not needed for purification. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.06.085

文献信息

• Fused heterocyclic derivative, medicinal composition containing the same, and medicinal use thereof
  申请人：Fushimi Nobuhiko

  公开号：US20060247179A1

  公开（公告）日：2006-11-02

  The present invention provides fused heterocyclic derivatives represented by the general formula: wherein R 1 represents H, halogen, OH, etc.; R 2 represents H, halogen or an alkyl group; R 3 and R 4 represent H, OH, halogen, etc.; Q represents alkylene, etc.; ring A represents aryl or heteroaryl; and G represents , or pharmaceutically acceptable salts thereof, or prodrugs thereof, which exhibit an excellent inhibitory activity in human SGLT and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications or obesity, pharmaceutical compositions comprising the same, and pharmaceutical uses thereof.

  本发明提供了由通式表示的融合杂环衍生物：其中R1代表H、卤素、OH等；R2代表H、卤素或烷基；R3和R4代表H、OH、卤素等；Q代表烷基等；环A代表芳基或杂芳基；G代表，或其药学上可接受的盐，或其前药，它们在人类SGLT中表现出优异的抑制活性，并且可用作预防或治疗与高血糖有关的疾病，如糖尿病、餐后高血糖、糖耐量受损、糖尿病并发症或肥胖症的药剂，以及它们的药用组合物和药用用途。
• A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate
  作者：M. Dell’Agli、S. Bellosta、L. Rizzi、G. V. Galli、M. Canavesi、F. Rota、R. Parente、E. Bosisio、S. Romeo

  DOI：10.1007/s00018-005-5422-7

  日期：2005.12

  Catechins are able to modulate the gelatinolytic activity of matrix metalloproteinase-9 (MMP-9) by reducing its release from macrophages. Gallocatechins decrease MMP-9 secretion by lowering MMP-9 promoter activity and mRNA levels. The effect appears to be dependent on some structural and stereochemical requirements. In this study, the relationship between chemical structure and activity was studied by testing the effect of analogues of (+/-)-gallocatechin-3-gallate (+/-)-GCG, selectively deprived of hydroxyl groups, on MMP-9 activity, transcription, and secretion. Our results indicate that (+/-)-GCG and (+/-)-catechin-3-gallate are characterized by a substitution pattern compatible with direct inhibition of MMP-9 activity. Conversely, when transcription was the target, (+/-)-trans-3-flavanol-3-benzoate, lacking all the hydroxyl groups, was the most effective both in lowering MMP-9 promoter activity and consequently protein secretion, and in inhibiting nuclear-factor-kappa B-driven transcription. Our results suggest that the structural requirements for enzyme inhibition are different from those necessary for targeting gene expression.
• FUSED HETEROCYCLIC DERIVATIVE, MEDICINAL COMPOSITION CONTAINING THE SAME, AND MEDICINAL USE THEREOF
  申请人：Kissei Pharmaceutical Co., Ltd.

  公开号：EP1609798B1

  公开（公告）日：2012-05-09
• Iinuma, Munekazu; Matsuura, Shin; Tanaka, Toshiyuki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1472 - 1476
  作者：Iinuma, Munekazu、Matsuura, Shin、Tanaka, Toshiyuki

  DOI：——

  日期：——
• ANSARI M. A.; MATHUR K. B. L.; AHLUWALIA V. K., INDIAN J. CHEM., 1978, B 16, NO 8 702-703
  作者：ANSARI M. A.、 MATHUR K. B. L.、 AHLUWALIA V. K.

  DOI：——

  日期：——