1-(4-hydroxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane | 39499-95-1

• 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: 1-(4-hydroxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane
• 英文别名: 3',4',5'-trimethoxy-bibenzyl-4-ol；4'-Hydroxy-3,4,5-trimethoxybibenzyl；Isoamoenylin；4-[2-(3,4,5-trimethoxyphenyl)ethyl]phenol
• CAS: 39499-95-1
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: WYMYMRJMKNLHSF-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  411.9±40.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1-(4-hydroxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane 在 sodium hydroxide 、 丙酮 作用下， 生成 1-<4-<2-(N,N-diethylamino)ethoxy>phenyl>-2-(3,4,5-trimethoxyphenyl)ethane
  参考文献：
  名称：

  Massarani et al., Farmaco, Edizione Scientifica, 1957, vol. 12, p. 462,468

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-三甲氧基苯乙酸 在 哌啶 、 甲醇 、 palladium on activated charcoal 作用下， 生成 1-(4-hydroxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane
  参考文献：
  名称：

  Massarani, Farmaco, Edizione Scientifica, 1957, vol. 12, p. 380,385

  摘要：

  DOI：

文献信息

• Synthesis and evaluation of analogs of (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene as potential cytotoxic and antimitotic agents
  作者：Mark Cushman、Dhanapalan Nagarathnam、D. Gopal、Hu Ming He、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00090a021

  日期：1992.6

  1a resembles that of the cis alkene 1. Additional inactive compounds prepared include the benzylisoquinoline series 28-32 as well as the protoberberines 38 and 39. Shortening the two-carbon bridge of 1a to a one-carbon bridge in the diphenylmethane 20 resulted in a decrease in cytotoxicity and tubulin polymerization inhibitory activity. Although the corresponding benzophenone 18 was as active as 1a as

  已经制备了一系列对苯二酚，并在五种人类癌细胞系A-549非小细胞肺癌，MCF-7乳腺癌，HT-29结肠癌，SKMEL-5黑色素瘤和MLM黑色素瘤中测试了细胞毒性。顺式斯蒂芬斯6a-f在所有五个细胞系中均被证明具有细胞毒性，其效力可与康美他汀A-4媲美。这些细胞毒性化合物都是微管蛋白聚合的有效抑制剂。相应的反丁苯橡胶7b-f作为微管蛋白聚合抑制剂没有活性，并且在5种癌细胞系中的细胞毒性明显较小。在二氢系列中，8b，8c和8f作为微管蛋白聚合抑制剂没有活性，而8a，8d和8e的活性低于相应的顺式化合物6a，6d和6e。菲23b缺乏对微管蛋白聚合的抑制活性和细胞毒性，作为前导化合物1的构象刚性类似物合成的Silbenes的活性表明，斯蒂芬酯的活性不是由于完全平面的构象。同样，构象受限的类似物26的无活性表明1a的生物活性构象与顺式烯烃1相似。制备的其他无活性化合物包括苄基异喹啉系列28-32以及
• 一种具有抗肿瘤活性的毛兰素衍生物、其药物组合物及用途
  申请人：郑州大学

  公开号：CN117185908A

  公开（公告）日：2023-12-08

  本发明公开一种毛兰素衍生物、其药物组合物及用途，属于医药技术领域。以毛兰素为母体，通过化学合成手段得到其衍生物，其特征在于，其结构如通式(1)：#imgabs0#抗肿瘤活性测定结果表明，本发明制备的毛兰素衍生物对食管鳞癌细胞株和非小细胞肺癌细胞株具有良好抑制作用。
• 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.
• Antineoplastic compounds
  申请人：ARIZONA BOARD OF REGENTS

  公开号：EP0276051B1

  公开（公告）日：1991-08-21
• PETTIT, GEORGE R.;SINGH, SHEO BUX;SCHMIDT, JEAN M.;NIVEN, MARGARET L.;HAM+, J. NATUR. PROD., 51,(1988) N 3, 517-527
  作者：PETTIT, GEORGE R.、SINGH, SHEO BUX、SCHMIDT, JEAN M.、NIVEN, MARGARET L.、HAM+

  DOI：——

  日期：——