(S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-2-nitrophenol | 1026776-58-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-2-nitrophenol
• 英文别名: 3-Nitrobakuchiol；4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]-2-nitrophenol
• CAS: 1026776-58-8
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: UTULJPIKXHBBCG-NCUBBLFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-2-nitrophenol 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到3-Aminobakuchiol
  参考文献：
  名称：

  Synthesis and structure–immunosuppressive activity relationships of bakuchiol and its derivatives

  摘要：

  A series of derivatives of bakuchiol were synthesized and tested in vitro for their cytotoxicity, and inhibition of T cell proliferation and B cell proliferation. The data obtained provided preliminary structure-activity relationships of the compounds as immunosuppressive activity. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.054
• 作为产物：
  描述：

  补骨脂酚 在 对甲苯磺酸 、 nickel(II) nitrate 作用下， 以 丙酮 为溶剂， 以51.8%的产率得到(S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)-2-nitrophenol
  参考文献：
  名称：

  补骨脂酚衍生物作为潜在抗癌剂的合成与评价。

  摘要：

  合成了一系列爆酚酚衍生物，并使用PX-478作为阳性对照评估了它们的抗增殖和对SMMC7721细胞系迁移的抑制活性。结果显示（S，E）-4-（7-甲氧基-3,7-二甲基-3-乙烯基辛-1-烯-1-基）苯酚（10）在测试的化合物中具有最佳活性，其中包括PX-478。另外，在每种剂量下，在transwell迁移和侵袭试验中，化合物10的抑制活性均比补骨脂酚高。在蛋白质印迹试验中，化合物10显示出有希望的下调HIF-1α及其相关下游蛋白MMP-2和MMP-9表达的能力。而且，该作用是剂量依赖性的，并且可能代表化合物10的抗癌活性的可能作用机理。

  DOI：

  10.3390/molecules23030515

文献信息

• Synthesis and structure–immunosuppressive activity relationships of bakuchiol and its derivatives
  作者：Hongli Chen、Xiaolong Du、Wei Tang、Yu Zhou、Jianping Zuo、Huijin Feng、Yuanchao Li

  DOI：10.1016/j.bmc.2007.11.054

  日期：2008.3

  A series of derivatives of bakuchiol were synthesized and tested in vitro for their cytotoxicity, and inhibition of T cell proliferation and B cell proliferation. The data obtained provided preliminary structure-activity relationships of the compounds as immunosuppressive activity. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and Evaluation of Bakuchiol Derivatives as Potential Anticancer Agents
  作者：Cheng-Zhu Wu、Da-Chuan Liu、Xing Guo、Yiqun Dai、Tao Ma、Hong-Mei Li、Qiang Huo

  DOI：10.3390/molecules23030515

  日期：——

  A series of bakuchiol derivatives were synthesized and evaluated for their anti-proliferative and the inhibitory activities on SMMC7721 cell line migration using PX-478 as a positive control. The results showed (S,E)-4-(7-methoxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (10) to have the best activity among the tested compounds, which included PX-478. In addition, compound 10 showed greater inhibitory

  合成了一系列爆酚酚衍生物，并使用PX-478作为阳性对照评估了它们的抗增殖和对SMMC7721细胞系迁移的抑制活性。结果显示（S，E）-4-（7-甲氧基-3,7-二甲基-3-乙烯基辛-1-烯-1-基）苯酚（10）在测试的化合物中具有最佳活性，其中包括PX-478。另外，在每种剂量下，在transwell迁移和侵袭试验中，化合物10的抑制活性均比补骨脂酚高。在蛋白质印迹试验中，化合物10显示出有希望的下调HIF-1α及其相关下游蛋白MMP-2和MMP-9表达的能力。而且，该作用是剂量依赖性的，并且可能代表化合物10的抗癌活性的可能作用机理。
• Novel bisstyryl derivatives of bakuchiol: Targeting oral cavity pathogens
  作者：Mallepally V. Reddy、Niranjan Thota、Payare L. Sangwan、Pankaj Malhotra、Furqan Ali、Inshad A. Khan、Swapandeep S. Chimni、Surrinder Koul

  DOI：10.1016/j.ejmech.2010.03.049

  日期：2010.7

  Novel bisstyryl derivatives of bakuchiol using Heck coupling reaction as the key step were synthesized and screened against a panel of six oral cavity pathogens for their antimicrobial activity. Four compounds (9-12) showed two to fourfold and four to eightfold better activity (MIC 0.25-16 mu g/ml) than bakuchiol and triclosan respectively. These compounds effectively inhibit the biofilm formation of single and multiple species at 2 - 8 x MICs. 4- and 4'-Hydroxy/methoxy styryl moieties of the bakuchiol derivatives play a pivotal role towards the activity as established in the SAR studies. Mechanism of action studies revealed microbial membrane structure disruption as the probable mode of action of these compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.