phenethyl (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylate | 1081273-75-7

• 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: phenethyl (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylate
• 英文别名: 2-Phenylethyl 3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoate；2-phenylethyl (E)-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoate
• CAS: 1081273-75-7
• 化学式: C₁₇H₁₅NO₆
• 分子量: 329.309
• InChiKey: WIKOXWOZNIRBTH-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-二羟基-5-硝基苯甲醛 在 哌啶 、 吡啶 、 potassium phosphate 作用下， 以 二甲基亚砜 为溶剂， 反应 72.5h， 生成 phenethyl (E)-3-(3,4-dihydroxy-5-nitrophenyl)acrylate
  参考文献：
  名称：

  血脑屏障可渗透的基于硝基儿茶酚的邻苯二酚O-甲基转移酶抑制剂具有降低肝毒性的潜力

  摘要：

  最近的努力集中在开发集中活性的COMT抑制剂上，由于与托卡朋有关的严重的肝毒性危险，它可以成为神经系统疾病（如帕金森氏病）的宝贵资产。开发了基于自然存在的咖啡酸和咖啡酸苯乙酯的新型硝基邻苯二酚COMT抑制剂。所有硝基儿茶酚衍生物在纳摩尔范围内均显示出对外周和大脑COMT的有效抑制。药物样衍生物13，15，和16预计在体外以50μM与大鼠原代肝细胞一起孵育时，它们会跨过血脑屏障，并且毒性显着低于tolcapone和entacapone。而且，它们独特的酸度和电化学性质降低了反应性醌-亚胺形成的机会，并因此降低了肝毒性的可能性。16的结合模式证实了与COMT的主要相互作用是通过硝基邻苯二酚环建立的，从而允许侧链衍生化以用于未来的铅优化工作。

  DOI：

  10.1021/acs.jmedchem.6b00666

文献信息

• Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
  作者：Chun-nian Xia、Hai-bo Li、Feng liu、Wei-xiao Hu

  DOI：10.1016/j.bmcl.2008.10.046

  日期：2008.12

  Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 mu M, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 mu M for CAPE against BEL-7404. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and antitumor activity of feruloyl and caffeoyl derivatives
  作者：Hui-zhen Chen、You-bao Chen、Ya-ping Lv、Fang Zeng、Juan Zhang、Yong-lie Zhou、Han-bing Li、Li-fei Chen、Bin-jie Zhou、Jian-rong Gao、Chun-nian Xia

  DOI：10.1016/j.bmcl.2014.08.024

  日期：2014.9

  We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg(-1). (C) 2014 Elsevier Ltd. All rights reserved.