1-(3,4-bis-benzyloxy-phenyl)-3-(2,4-dihydroxy-phenyl)-propane-1,3-dione | 883242-48-6

• 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: 1-(3,4-bis-benzyloxy-phenyl)-3-(2,4-dihydroxy-phenyl)-propane-1,3-dione
• 英文别名: 1-(2,4-dihydroxyphenyl)-3-(3,4-dibenzyloxyphenyl)-1,3-propanedione；1-(3,4-bis-benzyloxyphenyl)-3-(2,4-dihydroxyphenyl)propane-1,3-dione；1-[3,4-bis(phenylmethoxy)phenyl]-3-(2,4-dihydroxyphenyl)propane-1,3-dione
• CAS: 883242-48-6
• 化学式: C₂₉H₂₄O₆
• 分子量: 468.506
• InChiKey: KPXQWVHFYSERTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3,4-bis-benzyloxy-phenyl)-3-(2,4-dihydroxy-phenyl)-propane-1,3-dione 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 0.5h， 生成 3',4'-dibenzyloxy-7-(2,3-epoxypropoxy)flavone
  参考文献：
  名称：

  Flavone-Based Novel Antidiabetic and Antidyslipidemic Agents

  摘要：

  The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 706, 90a, and 906 of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations.

  DOI：

  10.1021/jm201107g
• 作为产物：
  描述：

  原儿茶酸 在 硫酸 、 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 20.0h， 生成 1-(3,4-bis-benzyloxy-phenyl)-3-(2,4-dihydroxy-phenyl)-propane-1,3-dione
  参考文献：
  名称：

  Flavone-Based Novel Antidiabetic and Antidyslipidemic Agents

  摘要：

  The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 706, 90a, and 906 of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations.

  DOI：

  10.1021/jm201107g
• 作为试剂：
  描述：

  六甲基二硅氮烷 、 正丁基锂 、 2,4-二羟基苯乙酮 、 3,4-二(苄氧基)苯甲酸乙酯 、 盐酸 在 氮气 、 ice 、 四氢呋喃 、 氯仿 、 Sodium sulfate-III 、 1-(3,4-bis-benzyloxy-phenyl)-3-(2,4-dihydroxy-phenyl)-propane-1,3-dione 、 异丙醇 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 33.5h， 以to give 11.0 g (49%) 4a as a white solid的产率得到3',4'-dibenzyloxy-7-hydroxy-flavone
  参考文献：
  名称：

  Novel flavonoids

  摘要：

  式(I)中的新型黄酮化合物，其中A和E一起形成C—C或C═C键；R1、R2、R3和R4为H、OH、O(CH2)n-芳基、n=0-8；O(CH2)nN(CH3)q，其中n=0-8，q=0-3；O(CH2)nOH，其中n=1-8；O(CH2)n-卤代物，其中n=1-8；O(CH2)nCOOH，其中n=0-8；O(CH2)nCOOR′，其中n=0-8且R′为C1-C8烷基或芳基；O(CH2)nCONH R″，其中n=0-8且R″为C1-C8烷基或芳基，以及单体、二聚体或三聚体形式或其类似物的糖类，但R1不为H，至少两个R2、R3和R4中的一个为H，最多一个R1、R2、R3和R4为OH，用于治疗药物诱导的毒性、多柔比星诱导的心脏毒性、自由基介导的疾病、肺病、癌症、糖尿病、心血管疾病或动脉硬化。

  公开号：

  US20020147353A1

文献信息

• Synthesis of Novel 3,7-Substituted-2-(3‘,4‘-dihydroxyphenyl)flavones with Improved Antioxidant Activity
  作者：Frédérique A. A. van Acker、Jos A. Hageman、Guido R. M. M. Haenen、Wim J. F. van der Vijgh、Aalt Bast、Wiro M. P. B. Menge

  DOI：10.1021/jm000951n

  日期：2000.10.1

  A series of 3,7-disubstituted-2-(3',4'-dihydroxyphenyl)flavones was synthesized as potential cardioprotective agents in doxorubicin antitumor therapy. The influence of substituents on the 3 and 7 positions of the flavone nucleus on radical scavenging and antioxidant properties was explored to improve the antioxidant activity of our lead compound monoHER. In the TEAC assay most compounds had a similar

  合成了一系列3,7-二取代-2-（3'，4'-二羟基苯基）黄酮作为阿霉素抗肿瘤治疗中潜在的心脏保护剂。探索了取代基对黄酮核的3和7位上自由基清除和抗氧化性能的影响，以改善铅化合物monoHER的抗氧化活性。在TEAC分析中，大多数化合物具有相似的效价（是trolox的效价的3.5-5倍），但在LPO分析中，IC（50）值在0.2到37 microM之间。通常，在LPO分析中，3-取代的黄酮（9a-j）是最有效的化合物。羟基的数目不是抗氧化剂活性的唯一先决条件。类黄酮的环A取代对于高活性不是必需的，但是7-OH基团的存在显着改变了抗氧化活性。
• [EN] SMALL MOLECULE ANTAGONISTS OF XIAP FAMILY PROTEINS<br/>[FR] PETITES MOLECULES ANTAGONISTES DE PROTEINES DE LA FAMILLE DES XIAP
  申请人：UNIV MICHIGAN

  公开号：WO2005092326A1

  公开（公告）日：2005-10-06

  The present invention relates to naturally occurring and chemically synthesized small molecule antagonists of XIAP family proteins. In particular, the present invention provides embelin and other XIAP inhibitors and methods of using these compounds as antagonists of the anti-apoptotic effects of XIAP family member proteins. The present invention also provides methods for treating diseases and pathologies (e.g., neoplastic diseases).

  本发明涉及自然存在和化学合成的XIAP家族蛋白小分子拮抗剂。特别地，本发明提供了embelin和其他XIAP抑制剂以及使用这些化合物作为XIAP家族成员蛋白抗凋亡效应的拮抗剂的方法。本发明还提供了治疗疾病和病理（例如，肿瘤性疾病）的方法。
• Oxy substituted flavones as antihyperglycemic and antidyslipidemic agents
  申请人：Pratap Ram

  公开号：US20060178373A1

  公开（公告）日：2006-08-10

  The present invention provides novel substituted flavone derivatives which exhibit anti-hyperglycemic and antidyslipedemic activity. The invention also provides a method for controlling type II diabetes and associated hyperlipidemic conditions in a mammal by administering compound of the present invention and compositions containing these derivatives.

  本发明提供了一种新型的取代黄酮衍生物，该衍生物表现出抗高血糖和抗血脂异常的活性。本发明还提供了一种通过给予本发明化合物和含有这些衍生物的组合物来控制哺乳动物的II型糖尿病和相关高脂血症状的方法。
• Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents
  作者：Hui Zhong、Jia Zhou、Xiao-Hong An、Ying-Rong Hua、Yi-Fan Lai、Rui Zhang、Owais Ahmad、Ye Zhang、Jing Shang

  DOI：10.1016/j.bioorg.2019.03.054

  日期：2019.6

  A bioactive component, 2',3,4,4'-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1-RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.
• NOVEL FLAVONOIDS
  申请人：VERENIGING VOOR CHRISTELIJK WETENSCHAPPELIJK ONDERWIJS

  公开号：EP1214308A2

  公开（公告）日：2002-06-19