[2-[3-(3,4-dimethoxyphenyl)prop-2-enoyloxy]-1-(2-iodo-3,4,5-trimethoxyphenyl)ethyl] 3-phenylprop-2-enoate | 1415215-74-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [2-[3-(3,4-dimethoxyphenyl)prop-2-enoyloxy]-1-(2-iodo-3,4,5-trimethoxyphenyl)ethyl] 3-phenylprop-2-enoate
• CAS: 1415215-74-5
• 化学式: C₃₁H₃₁IO₉
• 分子量: 674.486
• InChiKey: NTGBOVKHLXWBGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3,4,5-trimethoxy-2-iodobenzaldehyde 在 四氧化锇 、 potassium tert-butylate 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 生成 [2-[3-(3,4-dimethoxyphenyl)prop-2-enoyloxy]-1-(2-iodo-3,4,5-trimethoxyphenyl)ethyl] 3-phenylprop-2-enoate
  参考文献：
  名称：

  1-(3,4,5-Trimethoxyphenyl)ethane-1,2-diyl esters, a novel compound class with potent chemoreversal activity

  摘要：

  1-(3,4,5-Trimethoxyphenyl)ethane-1,2-diyl esters, which share a fragment from (+/-)-3'-O-4'-O-bis(3,4-dimethoxycinnamoyl)-cis-khellactone (DMDCK) and 3'R,4'R-disubstituted-2',2'-dimethyldihydropyrano[2,3-f]chromone (DSP), exhibited remarkable chemoreversal activity on multidrug resistant human nasopharyngeal carcinoma (KB) when combined with three anticancer drugs, paclitaxel, vincristine and doxorubicin. Among 15 novel synthesized analogs, bis-trimethoxybenzoyl derivative 15 was the most active (340-fold more active than verapamil when used with vincristine) followed by two di-cinnamoyl derivatives, 10 and 11, and then di-cyclohexanecarbonyl derivative 9. All aliphatic chain derivatives, 3-5, showed no activity. Structure-activity relationship study indicated that a di-ester structure was critical to enhance the activity resulting from the maintenance of the spatial arrangement proposed by the pharmacophore based on the verapamil-binding site. Further mechanism of action study showed 15 inhibited mainly P-glycoprotein efflux pump function, while 13 exhibited an additional multidrug resistance-associated protein efflux pump function. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.096