14-octanoyl andrographolide | 1239575-68-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 14-octanoyl andrographolide
• 英文别名: 14-octanoylandrographolide；[(3S,4E)-4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-oxooxolan-3-yl] octanoate
• CAS: 1239575-68-8
• 化学式: C₂₈H₄₄O₆
• 分子量: 476.654
• InChiKey: TXLJIPPNWWDWMS-GYLKUQNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(3S,4E)-4-[2-[(4aR,6aS,7R,10aS,10bR)-3,3,6a,10b-tetramethyl-8-methylidene-1,4a,5,6,7,9,10,10a-octahydronaphtho[2,1-d][1,3]dioxin-7-yl]ethylidene]-5-oxooxolan-3-yl] octanoate 在 水 、 溶剂黄146 作用下， 反应 0.5h， 以37.9%的产率得到14-octanoyl andrographolide
  参考文献：
  名称：

  Design, synthesis and antibacterial activity of novel andrographolide derivatives

  摘要：

  A series of andrographolide derivatives were synthesized through a facile condensation reaction with different carboxylic acids. The new compounds were characterized and screened for their antibacterial activities. A number of the new compounds significantly reduced bacterial quorum sensing virulence factors production in Pseudomonas aeruginosa, essential for pathogenesis. Compound 11b showed the best activity among all the new compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.094

文献信息

• Enzymatic synthesis and antibacterial activity of andrographolide derivatives
  作者：Zhi-Gang Chen、Quan Zhu、Min-Hua Zong、Zhen-Xin Gu、Yong-Bin Han

  DOI：10.1016/j.procbio.2011.05.011

  日期：2011.8

  A series of andrographolide derivatives have been synthesized through enzymatic acylation reactions. Immobilized Candida antarctica lipase B (Novozym 435) was found to be a useful biocatalyst for the 35-gram scale syntheses of these acylated derivatives, and the biocatalyst displayed excellent regioselectivity and high operational stability during the transformation. The 14-substituted andrographolide derivative was the sole detectable product from each acylation reaction. The acylated andrographolides showed antibacterial activity against representative Gram-positive and Gram-negative bacteria [with minimal inhibitory concentrations (MICs) as low as 4 mu g/mL], whereas andrographolide exhibited no such activity. Chain length of acyl moiety on the lactone-ring at the C-14 position plays an important role in determining the potency of the antibacterial activity. These results indicate an enzymatic modification was not only facile and green, but an effective method for the preparation of an andrographolide monoester. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, synthesis and antibacterial activity of novel andrographolide derivatives
  作者：Zhongli Wang、Pei Yu、Gaoxiao Zhang、Lipeng Xu、Dingyuan Wang、Liang Wang、Xiangping Zeng、Yuqiang Wang

  DOI：10.1016/j.bmc.2010.04.094

  日期：2010.6.15

  A series of andrographolide derivatives were synthesized through a facile condensation reaction with different carboxylic acids. The new compounds were characterized and screened for their antibacterial activities. A number of the new compounds significantly reduced bacterial quorum sensing virulence factors production in Pseudomonas aeruginosa, essential for pathogenesis. Compound 11b showed the best activity among all the new compounds. (C) 2010 Elsevier Ltd. All rights reserved.