(Z)-1-<4-(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene | 89946-05-4

• 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: (Z)-1-<4-(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene
• 英文别名: cis-3,4',5-tri(benzyloxy)stilbene；(Z)-1-(4-(benzyloxy)phenyl)-2-(3,5-bis(benzyloxy)phenyl) ethene；(Z)-1-(4-(benzyloxy)phenyl)-2-(3,5-bis(benzyloxy)phenyl)ethene；(Z)-1-[4-(benzyloxy)phenyl]-2-(3,5-bis(benzyloxy)phenyl)ethene；1,3-bis(phenylmethoxy)-5-[(Z)-2-(4-phenylmethoxyphenyl)ethenyl]benzene
• CAS: 89946-05-4
• 化学式: C₃₅H₃₀O₃
• 分子量: 498.621
• InChiKey: DNTQLVRXOUFTAQ-MSUUIHNZSA-N

物化性质

• 沸点：
  678.9±50.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1-<4-(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene 在 碘 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以100%的产率得到白藜芦醇三苄醚
  参考文献：
  名称：

  Method for the conversion of a Z-isomer into E-isomer

  摘要：

  一种将通式（II）中的（Z）-1-（3,5-二取代苯基）-2-（4-取代苯基）乙烯转化为通式（I）中的（E）-1-（3,5-二取代苯基）-2-（4-取代苯基）乙烯的方法，其中R1、R2和R3相同或不同，且独立地代表（C1-C4）烷基，（C1-C4）烷氧基（C1-C4）烷基，（C1-C4）烷氧基（C1-C4）烷氧基（C1-C4）烷基，烯丙基，乙烯基，硅基，甲酰基，酰基，芳基（C1-C4）烷基或取代芳基（C1-C4）烷基基团。本发明还提供了一种将通过上述方法制备的通式（I）中的（E）-1-（3,5-二取代苯基）-2-（4-取代苯基）乙烯转化为通式（III）中的E-白藜芦醇的方法。

  公开号：

  US20040015020A1
• 作为产物：
  描述：

  3,5-二苄氧基苯甲醇 在 sodium hydride 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (Z)-1-<4-(benzyloxy)phenyl>-2-<3,5-bis(benzyloxy)phenyl>ethene
  参考文献：
  名称：

  Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogs of piceatannol

  摘要：

  A series of hydroxylated trans-stilbenes related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxystilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function. A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product. Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly. The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.

  DOI：

  10.1021/jm00072a015

文献信息

• Synthesis and Biological Evaluation of Resveratrol and Analogues as Apoptosis-Inducing Agents
  作者：Marinella Roberti、Daniela Pizzirani、Daniele Simoni、Riccardo Rondanin、Riccardo Baruchello、Caterina Bonora、Filippo Buscemi、Stefania Grimaudo、Manlio Tolomeo

  DOI：10.1021/jm030785u

  日期：2003.7.1

  Resveratrol 1 (3,4',5-trihydroxy-trans-stilbene), a phytoalexin present in grapes and other food products, has recently been suggested as a potential cancer chemopreventive agent based on its striking inhibitory effects on cellular events associated with cancer initiation, promotion, and progression. This triphenolic stilbene has also displayed in vitro growth inhibition in a number of human cancer cell lines. In this context, a series of cis- and trans-stilbene-based resveratrols were prepared with the aim of discovering new lead compounds with clinical potential. All the synthesized compounds were tested in vitro for cell growth inhibition and the ability to induce apoptosis in HL60 promyelocytic leukemia cells. The tested trans-stilbene derivatives were less potent than their corresponding cis isomers, except for trans-resveratrol, whose cis isomer was less active. The best results were obtained with compounds 11b and 7b, the cis-3,5-dimethoxy derivatives of rhapontigenin 10a (3,5,3'-trihydroxy-4'methoxy-trans-stilbene) and its 3'-amino derivative 10b, respectively, which showed apoptotic activity at nanomolar concentrations. The corresponding trans isomers 12b and 8b were less active both as antiproliferative and as apoptosis-inducing agents. Of interest, 11b and 7b were active toward resistant HL60R cells and their activity was higher than that of several classic chemotherapeutic agents. The flow cytometry assay showed that at 50 nM compounds 7b or 11b were able to recruit almost all cells in the apoptotic sub-G(0)-G(1) peek, thus suggesting that the main mechanism of cytotoxicity of these compounds could be the activation of apoptosis. These data indicate unambiguously that structural alteration of the stilbene motif of resveratrol can be extremely effective in producing potent apoptosis-inducing agents.
• US6844471B2
  申请人：——

  公开号：US6844471B2

  公开（公告）日：2005-01-18
• [EN] METHOD FOR THE CONVERSION OF A Z-ISOMER INTO E-ISOMER<br/>[FR] MÉTHODE DE CONVERSION D'UN ISOMÈRE Z EN UN ISOMÈRE E
  申请人：ORCHID CHEMICALS & PHARM LTD

  公开号：WO2004009539A2

  公开（公告）日：2004-01-29

  A method of converting (Z)-1-(3,5-disubstituted phenyl)-2-(4-substituted phenyl)ethene of general formula (II) to (E)-1-(3,5-disubstituted phenyl)-2-(4-substituted phenyl)ethene of general formula (I). wherein R1, R2, R3 are same or different and independently represent (C1-C4)alkyl, (C1-C4)alkoxy(C1-C4)alkyl, (C1-C4)alkoxy(C1-C4)alkoxy(C1-C4)alkyl, allyl, vinyl, silyl, formyl, acyl, aryl(C1-C4)alkyl or substituted aryl(C1-C4)alkyl group and also provides a method for subsequent conversion of (E)-1-(3,5-disubstituted phenyl)-2-(4-substituted phenyl)ethene of general formula (I) prepared by a process described above to E-resveratrol of the formula (III).
• Synthesis and protein-tyrosine kinase inhibitory activity of polyhydroxylated stilbene analogs of piceatannol
  作者：Kshitij Thakkar、Robert L. Geahlen、Mark Cushman

  DOI：10.1021/jm00072a015

  日期：1993.10

  A series of hydroxylated trans-stilbenes related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxystilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function. A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product. Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly. The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.
• Method for the conversion of a Z-isomer into E-isomer
  申请人：ORCHID CHEMICALS AND PHARMACEUTICALS LIMITED

  公开号：US20040015020A1

  公开（公告）日：2004-01-22

  A method of converting (Z)-1-(3,5-disubstituted phenyl)-2-(4-substituted phenyl)ethene of general formula (II) to (E)-1-(3,5-disubstituted phenyl)-2-(4-substituted phenyl)ethene of general formula (I) 1 wherein R 1 , R 2 and R 3 are same or different and independently represent (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy(C 1 -C 4 )alkoxy(C 1 -C 4 )alkyl, allyl, vinyl, silyl, formyl, acyl, aryl(C 1 -C 4 )alkyl or substituted aryl(C 1 -C 4 )alkyl group. The present invention also provides a process for the conversion of (E)-1-(3,5-disubstituted phenyl)-2-(4-substituted phenyl)ethene of general formula (I) prepared by a process described above to E-resveratrol of the formula (III). 2

  一种将通式（II）中的（Z）-1-（3,5-二取代苯基）-2-（4-取代苯基）乙烯转化为通式（I）中的（E）-1-（3,5-二取代苯基）-2-（4-取代苯基）乙烯的方法，其中R1、R2和R3相同或不同，且独立地代表（C1-C4）烷基，（C1-C4）烷氧基（C1-C4）烷基，（C1-C4）烷氧基（C1-C4）烷氧基（C1-C4）烷基，烯丙基，乙烯基，硅基，甲酰基，酰基，芳基（C1-C4）烷基或取代芳基（C1-C4）烷基基团。本发明还提供了一种将通过上述方法制备的通式（I）中的（E）-1-（3,5-二取代苯基）-2-（4-取代苯基）乙烯转化为通式（III）中的E-白藜芦醇的方法。