3',4'-dibenzyloxy-7-hydroxy-flavone | 307520-98-5

• 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: 3',4'-dibenzyloxy-7-hydroxy-flavone
• 英文别名: 3',4'-dibenzyloxy-7-hydroxyflavone；2-[3,4-bis(phenylmethoxy)phenyl]-7-hydroxychromen-4-one
• CAS: 307520-98-5
• 化学式: C₂₉H₂₂O₅
• 分子量: 450.491
• InChiKey: NPRPMDALMIMTPV-UHFFFAOYSA-N

物化性质

• 熔点：
  245.4-245.8 °C
• 沸点：
  663.7±55.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3',4'-dibenzyloxy-7-hydroxy-flavone 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 、 二甲基亚砜 为溶剂， 反应 61.0h， 生成 N-(3-(3',4'-dihydroxyflavon-7-yl)oxypropyl)-N,N,N-trimethylammonium chloride
  参考文献：
  名称：

  具有改善的抗氧化活性的新型3,7-取代的-2-（3'，4'-二羟基苯基）黄酮的合成。

  摘要：

  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。

  DOI：

  10.1021/jm000951n
• 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 、 异丙醇 、 丙酮 为溶剂， 反应 20.0h， 生成 3',4'-dibenzyloxy-7-hydroxy-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

文献信息

• Novel flavonoids
  申请人：Vereniging christelijk wetenschappelijk anderwijs

  公开号：US20020147353A1

  公开（公告）日：2002-10-10

  Novel flavonoids of formula (I) 1 where A and E form together a C—C or C═C bond; R 1 , R 2 , R 3 , and R 4 are H, OH, O(CH2) n — aromatic group, n=0-8; O(CH 2 ) n N(CH 3 ) q with n=0-8, q=0-3; O(CH 2 ) n OH with n=1-8; O(CH 2 ) n -halide with n=1-8; O(CH 2 ) n COOH with n=0-8; O(CH 2 ) n COOR′ with n=0-8 and R′ is C 1 -C 8 alkyl or an aromatic group; O(CH 2 ) n CONH R″ with n=0-8 and R″ is C 1 -C 8 alkyl or an aromatic group, and sugars in mono-, di- or trimeric form or analogues thereof, with the proviso that R 1 is not H, at least two of R 2 , R 3 and R 4 are H, and at most one of R 1 , R 2 , R 3 and R 4 is OH, are useful for the treatment of drug-induced toxicity, doxorubicin-induced cardiotoxicity, free radical mediated diseases, lung diseases, cancer, diabetes mellitus, cardiovascular disease, or arteriosclerosis.

  化学式（I）的新型黄酮类化合物，其中A和E共同形成C—C或C═C键；R1、R2、R3和R4分别为H、OH、O(CH2)n—芳香基团，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-卤代基，其中n=1-8；O(CH2)nCOOH，其中n=0-8；O(CH2)nCOOR′，其中n=0-8，R′为C1-C8烷基或芳香基团；O(CH2)nCONH R″，其中n=0-8，R″为C1-C8烷基或芳香基团，并含有单体、二聚体或三聚体形式的糖或其类似物，但R1不是H，至少两个R2、R3和R4中有一个是H，至多一个是OH，这些化合物可用于治疗药物诱导的毒性、阿霉素诱导的心脏毒性、自由基介导的疾病、肺部疾病、癌症、糖尿病、心血管疾病或动脉粥样硬化。
• [EN] OXY SUBSTITUTED FLAVONES AS ANTIHYPERGLYCEMIC AND ANTIDYSLIPIDEMIC AGENTS<br/>[FR] FLAVONES SUBSTITUES PAR HYDROXY UTILISES EN TANT QU'AGENTS ANTI-HYPERGLYCEMIQUES ET ANTI-DYSLIPIDEMIQUES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2006040621A1

  公开（公告）日：2006-04-20

  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.

  本发明提供了新颖的取代黄酮衍生物，表现出抗高血糖和抗血脂异常活性。该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中II型糖尿病和相关高血脂症状的方法。
• [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。
• Flavonoid Compounds and Uses Thereof
  申请人：Jarrott Bevyn

  公开号：US20090130051A1

  公开（公告）日：2009-05-21

  Novel flavonoid compounds having anti-oxidant activity are described. The compounds and compositions have been shown to exhibit anti-oxidant properties and are particularly useful in the treatment of ischemia and reperfusion injuries. The invention also describes a method to chemically synthesize such flavonoid compounds and test their efficacy. Such compounds and corresponding pharmaceutically acceptable derivatives and/or salts have uses in the areas of pharmaceuticals, nutraceutical, and veterinary applications.

  本发明描述了具有抗氧化活性的新型黄酮类化合物。这些化合物和组合物已被证明具有抗氧化性质，特别适用于缺血和再灌注损伤的治疗。本发明还描述了一种化学合成这种黄酮类化合物并测试其功效的方法。这些化合物及其对应的药学上可接受的衍生物和/或盐在制药、保健品和兽医应用领域中有用。