(Z)-4-<2-(3',4',5'-Trimethoxyphenyl)ethenyl>phenol | 134029-60-0

• 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)-4-<2-(3',4',5'-Trimethoxyphenyl)ethenyl>phenol
• 英文别名: (Z)-1-(4-hydroxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene；(Z)-2-(4-hydroxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethene；4'-Hydroxy-3,4,5-trimethoxy-(z)-stilbene；4-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
• CAS: 134029-60-0
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: PGNACKMMQGBVTN-PLNGDYQASA-N

物化性质

• 熔点：
  196-198 °C
• 沸点：
  440.2±40.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (Z)-4-<2-(3',4',5'-Trimethoxyphenyl)ethenyl>phenol 在 盐酸 、 sodium hydroxide 、 sodium dithionite 、 三氟乙酸 、 sodium nitrite 、 亚硝酸异戊酯 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 26.25h， 生成 6-Diazo-4-<(Z)-2-(3',4',5'-trimethoxyphenyl)ethenyl>-2,4-cyclohexadien-1-one
  参考文献：
  名称：

  Potential Photoaffinity Labels for Tubulin. Synthesis and Evaluation of Diazocyclohexadienone and Azide Analogs of Colchicine, Combretastatin, and 3,4,5-Trimethoxybiphenyl

  摘要：

  Analogs of tubulin assembly inhibitors such as colchicine, combretastatin, and 3,4,5-trimethoxybiphenyl which incorporate a 6-diazo-2,4-cyclohexadienone (o-quinone diazide) ring have been synthesized and characterized. The compounds synthesized include 6-diazo-4-(2',3',4'-trimethoxyphenyl)cyclohexa-2,4-dien-1-one and its 3-methyl and 3-ethyl analogs (1a-c), 6-diazo-3-(2,3,4-trimethoxyphenyl)-2,4-cyclohexadien-1-one and its 4-methyl and 4-ethyl derivatives (2a-c), 4-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dienone (3), 3-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dien-1-one (4), the corresponding dihydro derivatives (5, 6) and two isomeric diazocyclohexadienones derived from N-acetylcolchinol (7, 8). Compounds in which the cyclohexadienone oxygen is approximately isostructural with carbonyl or hydroxy functions of the parent compounds exhibit good activity in the tubulin assembly inhibition assay. 2'-Alkyl-4'azido-3,4,5-trimethoxy-1,1'-biphenyls also show good activity as tubulin assembly inhibitors.

  DOI：

  10.1021/jo00094a048
• 作为产物：
  描述：

  4-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧基]-苯甲醇 在 四丁基氟化铵 、 sodium hexamethyldisilazane 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 47.08h， 生成 (Z)-4-<2-(3',4',5'-Trimethoxyphenyl)ethenyl>phenol
  参考文献：
  名称：

  Potential Photoaffinity Labels for Tubulin. Synthesis and Evaluation of Diazocyclohexadienone and Azide Analogs of Colchicine, Combretastatin, and 3,4,5-Trimethoxybiphenyl

  摘要：

  Analogs of tubulin assembly inhibitors such as colchicine, combretastatin, and 3,4,5-trimethoxybiphenyl which incorporate a 6-diazo-2,4-cyclohexadienone (o-quinone diazide) ring have been synthesized and characterized. The compounds synthesized include 6-diazo-4-(2',3',4'-trimethoxyphenyl)cyclohexa-2,4-dien-1-one and its 3-methyl and 3-ethyl analogs (1a-c), 6-diazo-3-(2,3,4-trimethoxyphenyl)-2,4-cyclohexadien-1-one and its 4-methyl and 4-ethyl derivatives (2a-c), 4-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dienone (3), 3-[Z-2-(3',4',5'-trimethoxyphenyl)ethenyl]-6-diazocyclohexa-2,4-dien-1-one (4), the corresponding dihydro derivatives (5, 6) and two isomeric diazocyclohexadienones derived from N-acetylcolchinol (7, 8). Compounds in which the cyclohexadienone oxygen is approximately isostructural with carbonyl or hydroxy functions of the parent compounds exhibit good activity in the tubulin assembly inhibition assay. 2'-Alkyl-4'azido-3,4,5-trimethoxy-1,1'-biphenyls also show good activity as tubulin assembly inhibitors.

  DOI：

  10.1021/jo00094a048

文献信息

• Synthesis and insect antifeedant activity of stilbene derivatives against Brontispa longissima Larvae
  作者：Ying-Qian Liu、Xiao-Jing Li、Chun-Yan Zhao、Yan Lu、Wen-Qun Li、Zhen-Ling Liu、Gang Feng、Liu Yang

  DOI：10.1007/s00044-012-0212-x

  日期：2013.5

  25 stilbene analogs were synthesized and evaluated for insect antifeedant activity against third-instar larvae of B. longissima for the first time. Among all the tested compounds, especially compounds 3a, 3c, and 6 showed pronounced antifeedant activities with AFC50 values of 0.218, 0.327, and 0.226 mg/mL, respectively. The different antifeedant activity ranges of these compounds indicated that variation

  继续我们的寻找以天然产物为基础的化合物来控制长双歧杆菌幼虫的研究，首次合成了25种二苯乙烯类似物并评估了其对长双歧杆菌第三龄幼虫的昆虫拒食活性。在所有测试的化合物中，尤其是化合物3a，3c和6在AFC 50中表现出明显的拒食活性值分别为0.218、0.327和0.226 mg / mL。这些化合物的拒食活性范围不同，表明二苯乙烯骨架中化学结构的变化显着影响了此类化合物的活性谱，并且从中揭示了一些重要的SAR信息。此外，要了解25种合成的二苯乙烯类似物对拒食活性的结构要求，可采用比较分子场分析（CoMFA）模型，该模型得出的留一法（LOO）交叉验证相关系数（q 2）为0.533和非交叉验证的相关系数（r 2）的数值为0.929。总之，这些初步结果可能在指导潜在的新抗饲料开发中对斯蒂芬苯酯的进一步修饰中有用。
• Functionalized stilbene derivatives as improved vascular targeting agents
  申请人：——

  公开号：US20030149003A1

  公开（公告）日：2003-08-07

  Novel stilbenoid compounds and their prodrug forms are disclosed, which serve as potent vascular targeting agents useful for the treatment of solid tumor cancers and other diseases associated with unwanted neovascularization. The novel stilbenoid compounds are tubulin-binding stilbenoid analogs structurally related to combretastatin A-1 and combretastatin A-4. The prodrug forms serve as potent vascular targeting agents (VTAs) useful for the treatment of solid tumor cancers and diseases associated with retinal neovascularization.

  本发明揭示了一种新型的苯乙烯类化合物及其前药形式，其作为强效的血管靶向剂，可用于治疗实体肿瘤癌和其他与不需要的新生血管化有关的疾病。这些新型的苯乙烯类化合物是微管结合的苯乙烯类类似物，其结构与康布雷他斯汀A-1和康布雷他斯汀A-4有关。前药形式作为强效的血管靶向剂（VTAs），可用于治疗实体肿瘤癌和与视网膜新生血管化有关的疾病。
• CYP1-Activation and Anticancer Properties of Synthetic Methoxylated Resveratrol Analogues
  作者：Ketan C. Ruparelia、Keti Zeka、Kenneth J. M. Beresford、Nicola E. Wilsher、Gerry A. Potter、Vasilis P. Androutsopoulos、Federico Brucoli、Randolph R. J. Arroo

  DOI：10.3390/molecules29020423

  日期：——

  (Z)-stilbenoid combretastatin A4, have been considered as promising lead compounds for the development of anticancer drugs. The antitumour properties of stilbenoids are known to be modulated by cytochrome P450 enzymes CYP1A1 and CYP1B1, which contribute to extrahepatic phase I xenobiotic and drug metabolism. Thirty-four methyl ether analogues of resveratrol were synthesised, and their anticancer properties were

  天然存在的二苯乙烯类化合物，如 （E）-二苯乙烯类白藜芦醇和 （Z）-二苯乙烯类化合物 combretastatin A4，已被认为是开发抗癌药物的有前途的先导化合物。已知二苯乙烯类化合物的抗肿瘤特性受细胞色素 P450 酶 CYP1A1 和 CYP1B1 的调节，这有助于肝外 I 期外源性物质和药物代谢。合成白藜芦醇的 34 种甲基醚类似物，并在一组人乳腺细胞系上使用 MTT 细胞增殖测定评估其抗癌特性。表达 CYP1 的乳腺肿瘤细胞系比不具有 CYP1 活性的细胞系受白藜芦醇类似物的影响明显更强。使用分离的 CYP1 酶的代谢研究提供了进一步的证据，证明 （E）-二苯乙烯类化合物可以成为这些酶的底物。通过与合成标准品和 LC-MS 共洗脱研究进行比较来确认代谢产物的结构。最有前途的二苯乙烯类化合物是 （E）-4,3′，4′，5′-四甲氧基二苯乙烯 （DMU212）。该化合物本身显示出低至中度的细胞毒性，但在
• Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization
  作者：Mark Cushman、Dhanapalan Nagarathnam、D. Gopal、Asit K. Chakraborti、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00112a036

  日期：1991.8

  An array of cis-, trans-, and dihydrostilbenes and some N-arylbenzylamines were synthesized and evaluated for their cytotoxicity in the five cancer cell cultures A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, and MLM melanoma. Several cis-stilbenes, structurally similar to combretastatins, were highly cytotoxic in all five cell lines and these were also found to be active as inhibitors of tubulin polymerization. The most active compounds also inhibited the binding of colchicine to tubulin. The most potent of the new compounds, both as a tubulin polymerization inhibitor and as a cytotoxic agent, was (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene (5a). This substance was almost as potent as combretastatin A-4 (1a), the most active of the combretastatins, as a tubulin polymerization inhibitor. Compound 5a was found to be approximately 140 times more cytotoxic against HT-29 colon adenocarcinoma cells and about 10 times more cytotoxic against MCF-7 breast carcinoma cells than combretastatin A-4. However, 5a was found to be about 20 times less cytotoxic against A-549 lung carcinoma cells, 30 times less cytotoxic against SKMEL-5 melanoma cells, and 7 times less cytotoxic against MLM melanoma cells than combretastatin A-4. The relative potencies 5a > 8a > 6a for the cis, dihydro, and trans compounds, respectively, as inhibitors of tubulin polymerization are in agreement with the relative potencies previously observed for combretastatin A-4 (1a), dihydrocombretastatin A-4 (1c), and trans-combretastatin A-4 (1b). The relative potencies 5a > 8a > 6a were also reflected in the results of the cytotoxicity assays. Structure-activity relationships of this group of compounds are also discussed.
• STILBENE DERIVATIVES AS ANTICANCER AGENTS
  申请人：Research Corporation Technologies, Inc.

  公开号：EP0641301A1

  公开（公告）日：1995-03-08