andrographolide-14-butanoate | 1201658-82-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: andrographolide-14-butanoate
• 英文别名: 14-butyrylandrographolide；[(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] butanoate
• CAS: 1201658-82-3
• 化学式: C₂₄H₃₆O₆
• 分子量: 420.546
• InChiKey: RJDBVBNMYCYART-DTBRIUQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  正丁酸乙烯酯 、 穿心莲内酯 以 丙酮 为溶剂， 反应 5.0h， 以96.3%的产率得到andrographolide-14-butanoate
  参考文献：
  名称：

  区域选择性和高效酶法合成抗菌穿心莲内酯衍生物

  摘要：

  拉丹烷二萜穿心莲内酯（1）是穿心莲的主要成分，已知具有广泛的生物活性。在这项研究中，通过使用Amano脂肪酶AK（荧光假单胞菌）作为生物催化剂合成了（1）的区域选择性单酯。在酰基供体的存在下，Amano脂肪酶AK能够对与（1）的C-14碳相连的羟基进行高效酯化。在各种合成的衍生物中，包括两种新化合物，如穿心莲内酯-14-丙酸酯（3）和穿心莲内酯-14-己酸酯（5）显示出对金黄色葡萄球菌的抗菌活性。最低抑菌浓度（MIC）较低，分别为4 µg / mL和16 µg / mL。此外，如FITC摄取和SEM成像研究所示，它们在各自的MIC处显示出较低的溶血活性，并且细菌细胞膜的通透性增加。

  DOI：

  10.1016/j.bmcl.2018.01.007

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.