5-O-hexadecanoyloxy-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-O-hexadecanoyloxy-1,4-naphthoquinone
• 英文别名: juglone palmitate；5-O-palmitoyljuglone；(5,8-Dioxonaphthalen-1-yl) hexadecanoate；(5,8-dioxonaphthalen-1-yl) hexadecanoate
• 化学式: C₂₆H₃₆O₄
• 分子量: 412.569
• InChiKey: OWMIMAVVSLLYQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-羟基对萘醌 、 棕榈酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到5-O-hexadecanoyloxy-1,4-naphthoquinone
  参考文献：
  名称：

  萘醌衍生物的合成，抗菌和抗真菌活性：结构-活性关系研究

  摘要：

  1,4-萘醌衍生物的合成备受关注，因为这些化合物作为抗疟疾，抗菌，抗真菌和抗癌剂具有很强的活性。合成了一系列50种萘醌衍生物，并使用肉汤微稀释法评估了其对大肠杆菌，铜绿假单胞菌，粪肠球菌，金黄色葡萄球菌，克鲁斯假丝酵母，副念珠菌和新隐球菌的抗菌和抗真菌活性。该念珠菌种是最易感的微生物。1,4-萘醌的卤素衍生物具有很强的活性，例如2-溴-5-羟基-1,4-萘醌，在金黄色葡萄球菌和2-chloro-5中的MIC为16 µg / mL时表现出抑制作用，8-二羟基-1,4-萘醌，在克鲁氏梭菌中的MIC为2 µg / mL 。这些化合物显示出较高的抗真菌活性，但抗菌活性非常低。由于药库的限制，结构-活性关系的研究对于寻找新的抗微生物药物非常重要。

  DOI：

  10.1007/s00044-016-1550-x

文献信息

• Synthesis, antibacterial and antifungal activities of naphthoquinone derivatives: a structure–activity relationship study
  作者：Juan M. Sánchez-Calvo、Gara R. Barbero、Guillermo Guerrero-Vásquez、Alexandra G. Durán、Mariola Macías、Manuel A. Rodríguez-Iglesias、José M. G. Molinillo、Francisco A. Macías

  DOI：10.1007/s00044-016-1550-x

  日期：2016.6

  4-naphthoquinone presented strong activity, e.g., 2-bromo-5-hydroxy-1,4-naphthoquinone, which exhibited inhibition at an MIC of 16 µg/mL in S. aureus, and 2-chloro-5,8-dihydroxy-1,4-naphthoquinone, with an MIC of 2 µg/mL in C. krusei. These compounds showed higher activity against fungi, but the antibacterial activities were very low. The study of structure–activity relationships is very important in the search

  1,4-萘醌衍生物的合成备受关注，因为这些化合物作为抗疟疾，抗菌，抗真菌和抗癌剂具有很强的活性。合成了一系列50种萘醌衍生物，并使用肉汤微稀释法评估了其对大肠杆菌，铜绿假单胞菌，粪肠球菌，金黄色葡萄球菌，克鲁斯假丝酵母，副念珠菌和新隐球菌的抗菌和抗真菌活性。该念珠菌种是最易感的微生物。1,4-萘醌的卤素衍生物具有很强的活性，例如2-溴-5-羟基-1,4-萘醌，在金黄色葡萄球菌和2-chloro-5中的MIC为16 µg / mL时表现出抑制作用，8-二羟基-1,4-萘醌，在克鲁氏梭菌中的MIC为2 µg / mL 。这些化合物显示出较高的抗真菌活性，但抗菌活性非常低。由于药库的限制，结构-活性关系的研究对于寻找新的抗微生物药物非常重要。
• A New, Simple and Efficient Method of Steglich Esterification of Juglone with Long-Chain Fatty Acids: Synthesis of a New Class of Non-Polymeric Wax Deposition Inhibitors for Crude Oil
  作者：Vitor Gilles、Mariana A. Vieira、Valdemar Lacerda Jr.、Eustáquio V. R. Castro、Reginaldo B. Santos、Ednilson Orestes、José W. M. Carneiro、Sandro J. Greco

  DOI：10.5935/0103-5053.20140216

  日期：——

  Direct esterification on naphthoquinone presented itself as a hard task. Usual methodologies apply acyl chloride in pyridine or anhydrides but with long-chain esters this procedure proved to be ineffective because of the low yields obtained. We present a new synthesis of long-chain esters of juglone based on Steglich esterification using a cheap Lewis acid as cocatalyst. Yields obtained are considerably better than those found previously. Computational chemistry was used to evaluate the effects of CeCl3 as cocatalyst. Prepared compounds were tested as wax deposition inhibitors in crude oil. Palmitic ester of juglone was able to lower 4 degrees C on the wax appearance temperature (WAT) of the studied oil, representing a reduction of precipitated normal paraffin of 1.5% m/m.
• Novel juglone and plumbagin 5- O derivatives and their in vitro growth inhibitory activity against apoptosis-resistant cancer cells
  作者：Serena Fiorito、Salvatore Genovese、Vito Alessandro Taddeo、Véronique Mathieu、Robert Kiss、Francesco Epifano

  DOI：10.1016/j.bmcl.2015.12.017

  日期：2016.1

  Juglone 1 an plumbagin 2 are plant secondary metabolites nowadays well known for their anticancer properties. In this study we synthesized analogues of 1 and 2 deriving from the functionalization of the OH group in position 5 with different side chains in form of esters and ethers. Therefore the growth inhibitory activities of these adducts were evaluated in vitro on six cancer cell lines using the MTT colorimetric assays along with the two natural parent compounds. The data revealed that these latter displayed the strongest growth inhibitory activities in vitro. Quantitative videomicroscopy analyses were then carried out on human U373 glioblastoma cells, which are characterized by various level of resistance to pro-apoptotic stimuli. We compared the naturally occurring reference compounds 1 and 2 with the derivatives exerting the best activities in terms of IC50 growth inhibitory values. These analyses showed that both juglone and plumbagin had a cytostatic effect on U373 cells and were able to overcome the intrinsic resistance of U373 cancer cells to pro-apoptotic stimuli. (C) 2015 Elsevier Ltd. All rights reserved.