(3,4-dihydroxyphenyl)(4-hydroxyphenyl)methanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3,4-dihydroxyphenyl)(4-hydroxyphenyl)methanone
• 英文别名: 3,4',5-trihydroxybenzophenone；(3,5-Dihydroxyphenyl)(4-hydroxyphenyl)methanone；(3,5-dihydroxyphenyl)-(4-hydroxyphenyl)methanone
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: QXRGOOONSJPVAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲醛 在 重铬酸吡啶 、 正丁基锂 、 4 A molecular sieve 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.25h， 生成 (3,4-dihydroxyphenyl)(4-hydroxyphenyl)methanone
  参考文献：
  名称：

  Antineoplastic Agents. 465. Structural Modification of Resveratrol:  Sodium Resverastatin Phosphate

  摘要：

  As an extension of structure/activity investigations of resveratrol (1), phenstatin (2c), and the cancer antiangiogenesis drug sodium combretastatin A-4 phosphate (2b), syntheses of certain related stilbenes (14) and benzophenones (16) were undertaken. The trimethyl ether derivative of (Z)-resveratrol (4a) exhibited the strongest activity (GI(50) = 0.01-0.001 mug/mL) against a minipanel of human cancer cell lines. A monodemethylated derivative (14c) was converted to prodrug 14n (sodium resverastatin phosphate) for further biological evaluation. The antitubulin and antimicrobial activities of selected compounds were also evaluated.

  DOI：

  10.1021/jm010119y

文献信息

• Structural modification of resveratrol: Sodium resverastatin phosphate
  申请人：Pettit R. George

  公开号：US20050240062A1

  公开（公告）日：2005-10-27

  Described herein are novel compounds having antineoplastic and antimicrobial activity, obtained via structural modifications of resveratrol and combretastatin A-4, methods for synthesis of these compounds, and their use in pharmaceutical composition and for use in the treatment of mammals having cancer. Examples of the novel compounds are: (Z)- and (E)-3,4′,5-trimethioxystilbene (4a, 4b); (Z)- and (E)-3,5-dimethoxy-4′-hydroxystilbene (14c, 14d); (Z)-and (E)-3-hydroxy-4′,5-dimethoxystilbene (14g, 14h);(Z)-and (E)-3,5-dihydroxy-4′-methoxy-stilbene (14k, 14l); sodium resverastatin dibenzyl phosphate ((Z)-3,5-dimethoxy-4-[O-bis(benzyl)phosphoryl]-stilbene) (14m); and sodium resverastatin phosphate (14n).

  本文描述了一些具有抗肿瘤和抗微生物活性的新化合物，这些化合物是通过对白藜芦醇和康布雷他汀A-4进行结构修饰而获得的，还介绍了这些化合物的合成方法以及它们在制药组合物中的使用和用于治疗患有癌症的哺乳动物的用途。新化合物的例子包括：(Z)-和(E)-3,4′,5-三甲氧基亚苄基苯乙烯(4a, 4b)；(Z)-和(E)-3,5-二甲氧基-4′-羟基亚苄基苯乙烯(14c, 14d)；(Z)-和(E)-3-羟基-4′,5-二甲氧基亚苄基苯乙烯(14g, 14h)；(Z)-和(E)-3,5-二羟基-4′-甲氧基-亚苄基苯乙烯(14k, 14l)；白藜芦醇二苄基磷酸钠((Z)-3,5-二甲氧基-4-[O-双苯基磷酸二苄酯基]-亚苄基苯乙烯)(14m)；以及白藜芦醇磷酸钠(14n)。
• Verfahren zur Herstellung von Benzophenonen
  申请人：BASF Aktiengesellschaft

  公开号：EP0361119A1

  公开（公告）日：1990-04-04

  Die Erfindung betrifft ein Verfahren zur Herstellung von Benzophenonen durch Kondensation von Benzoesäuren und Aromaten aus der Benzolreihe mittels Bortrifluorid in Nitrobenzol als Reaktionsmedium.

  本发明涉及一种以硝基苯中的三氟化硼为反应介质，通过苯甲酸和苯系列芳香族化合物缩合制备二苯甲酮的工艺。
• US7705188B2
  申请人：——

  公开号：US7705188B2

  公开（公告）日：2010-04-27
• [EN] STRUCTURAL MODIFICATION OF RESVERATROL: SODIUM RESVERASTATIN PHOSPHATE<br/>[FR] MODIFICATION STRUCTURELLE DU RESVERATROL: PHOSPHATE DE RESVERASTATINE DE SODIUM
  申请人：UNIV ARIZONA

  公开号：WO2003086414A1

  公开（公告）日：2003-10-23

  Described herein are novel compounds having antineoplastic and antimicrobial activity, obtained via structural modifications of resveratrol and combretastatin A-4, methods for synthesis of these compounds, and their use in pharmaceutical composition and for use in the treatment of mammals having cancer. Examples of the novel compounds are: (Z)- and (E)- 3,4',5-trimethoxystilbene (4a, 4b); (Z)- and (E)-3,5-dimethoxy-4'-hydroxystilbene (14c, 14d); (Z)-and (E)-3-hydroxy-4',5-dimethoxystilbene (14g, 14h); (Z)-and (E)-3,5-dihydroxy-4'-methoxy-stilbene (14k, 14l); sodium resverastatin dibenzyl phosphate ((Z)-3,5-dimethoxy-4-[O-bis(benzyl)phosphoryl]-stilbene) (14m); and sodium resverastatin phosphate (14n).
• Antineoplastic Agents. 465. Structural Modification of Resveratrol:  Sodium Resverastatin Phosphate
  作者：George R. Pettit、Matthew P. Grealish、M. Katherine Jung、Ernest Hamel、Robin K. Pettit、J.-Charles Chapuis、Jean M. Schmidt

  DOI：10.1021/jm010119y

  日期：2002.6.1

  As an extension of structure/activity investigations of resveratrol (1), phenstatin (2c), and the cancer antiangiogenesis drug sodium combretastatin A-4 phosphate (2b), syntheses of certain related stilbenes (14) and benzophenones (16) were undertaken. The trimethyl ether derivative of (Z)-resveratrol (4a) exhibited the strongest activity (GI(50) = 0.01-0.001 mug/mL) against a minipanel of human cancer cell lines. A monodemethylated derivative (14c) was converted to prodrug 14n (sodium resverastatin phosphate) for further biological evaluation. The antitubulin and antimicrobial activities of selected compounds were also evaluated.