3,5-di(tert-butyldimethylsilyloxy)-4'-methoxybenzhydrol | 441351-45-7

• 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: 3,5-di(tert-butyldimethylsilyloxy)-4'-methoxybenzhydrol
• 英文别名: 3,5-Di-(tert-butyldimethylsilyloxy)-4'-methoxybenzhydrol；[3,5-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]-(4-methoxyphenyl)methanol
• CAS: 441351-45-7
• 化学式: C₂₆H₄₂O₄Si₂
• 分子量: 474.788
• InChiKey: YRCMMFQIBSEZSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-di(tert-butyldimethylsilyloxy)-4'-methoxybenzhydrol 在 重铬酸吡啶 、 4 A molecular sieve 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3,5-Dihydroxyphenyl)-(4-methoxyphenyl)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
• 作为产物：
  描述：

  3,5-二羟基苯甲醛 在 正丁基锂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 3,5-di(tert-butyldimethylsilyloxy)-4'-methoxybenzhydrol
  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)。
• Structural modification of resveratrol: sodium resverastatin phosphate
  申请人：Arizona Board of Regents, a body corporate of the State of Arizona, Acting for and on Behalf of the Arizona State University

  公开号：US07705188B2

  公开（公告）日：2010-04-27

  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-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).

  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塔斯汀A-4进行结构修饰得到的。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应用，以及用于治疗患有癌症的哺乳动物的用途。其中一些新化合物的例子包括：(Z)-和(E)-3,4′,5-三甲氧基亚苄基乙烯（4a, 4b）；(Z)-和(E)-3,5-二甲氧基-4′-羟基亚苄基乙烯（14c, 14d）；(Z)-和(E)-3-羟基-4′,5-二甲氧基亚苄基乙烯（14g, 14h）；(Z)-和(E)-3,5-二羟基-4′-甲氧基-亚苄基乙烯（14k, 14l）；白藜芦醇二苄基磷酸钠（(Z)-3,5-二甲氧基-4-[O-双苄基磷酸酯基]-亚苄基乙烯）（14m）和白藜芦醇磷酸钠（14n）。