2-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]phenol | 1585206-34-3

• 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: 2-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]phenol
• 英文别名: 2-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
• CAS: 1585206-34-3
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: ZKCMIXSEYCUMMF-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苄氯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 2-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]phenol 、 2-[(E)-2-(3,4,5-trimethoxyphenyl)vinyl]phenol
  参考文献：
  名称：

  SAR study on arylmethyloxyphenyl scaffold: Looking for a P-gp nanomolar affinity

  摘要：

  Starting from the previously developed P-gp ligands 1a and 1b (EC50 = 0.25 mu M and 0.65 mu M, respectively), new arylmethyloxyphenyl derivatives have been synthesized as P-gp modulators in order to investigate: (i) the effect of small electron-donor groups (OMe) (5-11), (ii) the effect of the replacement of methoxy groups with an electron-withdrawal substituent (Cl) on C-ring (13) (iii) the effect induced by the replacement of C-ring with heteroaromatic cycles such as thiophene and pyrimidine (13, 15, 16), (iv) the effect induced by molecular constriction on C ring (14,17,18) on P-gp modulating activity. The results demonstrated that P-gp inhibition potency is strongly correlated to the number of methoxy groups in the A-ring whereas the methoxylation of C-ring seems to poorly affect P-gp activity. The best result was found for compound 10 that displays a nanomolar affinity (EC50 = 7.1 nM) towards P-gp pump and, in the meantime lacks of activity against MRP1 pump. (C) 2014 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.02.051

文献信息

• Synthesis and antiproliferative evaluation of 2-hydroxylated (E)-stilbenes
  作者：Yan Zhang、Mingyun Shen、Sunliang Cui、Tingjun Hou

  DOI：10.1016/j.bmcl.2014.10.009

  日期：2014.12

  A simple synthesis of 2-hydroxylated (E)-stilbenes was accomplished in good yields via oxidative coupling of 2-hydroxystyrenes and arylboronic acids, with Rh(III)-catalyst and Cu(OAc)(2) as oxidant. The antiproliferative evaluation of all the synthesized compounds were assessed on four different human cancer cell lines (Colo-205, MDA-468, HT29, and MGC80-3), and the results showed that several compounds exhibit strong antiproliferative activities (up to IC50 = 35 nM for MGC80-3). (C) 2014 Elsevier Ltd. All rights reserved.