3-Aminobakuchiol | 1026776-60-2

• 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: 3-Aminobakuchiol
• 英文别名: 2-amino-4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenol
• CAS: 1026776-60-2
• 化学式: C₁₈H₂₅NO
• 分子量: 271.403
• InChiKey: BKVDKBGINROADH-NCUBBLFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  20
• 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：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Aminobakuchiol 、 尿素 在 吡啶 作用下， 反应 12.0h， 以99%的产率得到5-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]-3H-1,3-benzoxazol-2-one
  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：

  (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

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.
• 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.