3-tert-butyldimethylsilyloxy-3',4,4',5'-tetramethyloxystilbene | 847063-26-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-tert-butyldimethylsilyloxy-3',4,4',5'-tetramethyloxystilbene
• 英文别名: Tert-butyl-[2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenoxy]-dimethylsilane
• CAS: 847063-26-7
• 化学式: C₂₄H₃₄O₅Si
• 分子量: 430.616
• InChiKey: UMDKFDJQYNOPRV-UHFFFAOYSA-N

物化性质

• 沸点：
  506.7±50.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-tert-butyldimethylsilyloxy-3',4,4',5'-tetramethyloxystilbene 在 盐酸 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 2-甲氧基-5-[2-(3,4,5-三甲氧基苯基)乙基]苯酚
  参考文献：
  名称：

  毛兰素及其衍生物组蛋白脱乙酰酶抑制剂的设计、合成及生物学评价

  摘要：

  利用天然产物花兰素或其衍生物的主导骨架设计合成了一系列新型HDAC抑制剂。其中，一些化合物表现出比毛兰素和SAHA更强的体外抗肿瘤活性，并对HDAC具有强效抑制作用。

  DOI：

  10.1002/cmdc.202300108
• 作为产物：
  描述：

  Tert-butyl-[2-methoxy-5-[(3,4,5-trimethoxyphenyl)methylsulfonylmethyl]phenoxy]-dimethylsilane 在 二溴二氟甲烷 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 12.0h， 以81%的产率得到3-tert-butyldimethylsilyloxy-3',4,4',5'-tetramethyloxystilbene
  参考文献：
  名称：

  A Ramberg–Bäcklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212

  摘要：

  已经开发出一种简洁的途径来合成可瑞替丁A-4，这是一种强效的微管蛋白聚合抑制剂，利用Ramberg-Backlund反应形成关键的（Z）-二苯乙烯单元；这种Ramberg-Backlund方法还被扩展用于制备（E）-二苯乙烯DMU-212，后者也具有令人感兴趣的生长抑制特性。

  DOI：

  10.1039/b702411h

文献信息

• New Method of Synthesis and Biological Evaluation of Some Combretastatin A-4 Analogues
  作者：Andrei Gavryushin、Yulia Malysheva、Sebastien Combes、Alexey Fedorov、Paul Knochel

  DOI：10.1055/s-0031-1290899

  日期：2012.5

  A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50 = 0.022-10.31 mu M).
• Heterocyclic and Phenyl Double-Bond-Locked Combretastatin Analogues Possessing Potent Apoptosis-Inducing Activity in HL60 and in MDR Cell Lines
  作者：Daniele Simoni、Giuseppina Grisolia、Giuseppe Giannini、Marinella Roberti、Riccardo Rondanin、Laura Piccagli、Riccardo Baruchello、Marcello Rossi、Romeo Romagnoli、Francesco Paolo Invidiata、Stefania Grimaudo、M. Katherine Jung、Ernest Hamel、Nicola Gebbia、Lucia Crosta、Vincenzo Abbadessa、Antonietta Di Cristina、Luisa Dusonchet、Maria Meli、Manlio Tolomeo

  DOI：10.1021/jm049622b

  日期：2005.2.1

  Two new series of combretastatin (CA-4) analogues have been prepared. The alkenyl motif of CA-4 was replaced either by a five-membered heterocyclic (isoxazoline or isoxazole) or by a six-membered ring (pyridine or benzene). The new compounds have been evaluated for their effects on tubulin assembly and for cytotoxic and apoptotic activities. Five compounds (18b, 20a, 21a, 34b, and 35b) demonstrated an attractive profile of cytotoxicity (IC50 < 1 muM) and apoptosis-inducing activity but poor antitubulin activity. The isoxazoline derivatives 18b, 20a, and 21a, demonstrated potent apoptotic activity different from that of natural CA-4. Their ability to block most cells in the G2 phase suggests that these compounds could act on targets different from the mitotic spindle. This would indicate activation of both the intrinsic and the extrinsic apoptotic pathways. The data suggest unambiguously that structural alteration of the stilbene motif of CA-4 can be extremely effective in producing potent apoptosis-inducing agents.
• A Ramberg–Bäcklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212
  作者：James E. Robinson、Richard J. K. Taylor

  DOI：10.1039/b702411h

  日期：——

  A concise route to combretastatin A-4, a potent inhibitor of tubulin polymerisation, using a Ramberg–Bäcklund reaction to form the key (Z)-stilbene unit has been developed; this Ramberg–Bäcklund approach has also been extended to prepare the (E)-stilbene DMU-212, which also possesses interesting growth inhibitory properties.

  已经开发出一种简洁的途径来合成可瑞替丁A-4，这是一种强效的微管蛋白聚合抑制剂，利用Ramberg-Backlund反应形成关键的（Z）-二苯乙烯单元；这种Ramberg-Backlund方法还被扩展用于制备（E）-二苯乙烯DMU-212，后者也具有令人感兴趣的生长抑制特性。
• Design, Synthesis, and Biological Evaluation of Histone Deacetylase Inhibitors Derived from Erianin and Its Derivatives
  作者：Yawen Yang、Qingqing Liu、Xinyi Wang、Shaohua Gou

  DOI：10.1002/cmdc.202300108

  日期：2023.7.3

  The dominant skeleton of the natural product erianin or its derivatives were used to design and synthesize a series of novel HDAC inhibitors. Among these, some compounds were found to show stronger in vitro antitumor activity than erianin and SAHA with potent inhibition on HDAC.

  利用天然产物花兰素或其衍生物的主导骨架设计合成了一系列新型HDAC抑制剂。其中，一些化合物表现出比毛兰素和SAHA更强的体外抗肿瘤活性，并对HDAC具有强效抑制作用。