5-O-octadecanoyloxy-1,4-naphthoquinone | 1340543-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-O-octadecanoyloxy-1,4-naphthoquinone
• 英文别名: 5-octadecanoyloxy-1,4-naphthoquinone；juglone stearate；(5,8-Dioxonaphthalen-1-yl) octadecanoate
• CAS: 1340543-23-8
• 化学式: C₂₈H₄₀O₄
• 分子量: 440.623
• InChiKey: MLNNBJMIFGETKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 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 、 硬脂酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 以52%的产率得到5-O-octadecanoyloxy-1,4-naphthoquinone
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.5935/0103-5053.20140216

文献信息

• Inhibitory effect of novel 5-O-acyl juglones on mammalian DNA polymerase activity, cancer cell growth and inflammatory response
  作者：Sayako Maruo、Isoko Kuriyama、Kouji Kuramochi、Kazunori Tsubaki、Hiromi Yoshida、Yoshiyuki Mizushina

  DOI：10.1016/j.bmc.2011.08.023

  日期：2011.10

  We previously found that vitamin K(3) (menadione, 2-methyl-1,4-naphthoquinone) inhibits the activity of human mitochondrial DNA polymerase gamma (pol gamma). In this study, we focused on juglone (5-hydroxy-1,4-naphthoquinone), which is a 1,4-naphthoquinone derivative, and chemically synthesized novel juglones conjugated with C2:0 to C22:6 fatty acid (5-O-acyl juglones). The chemically modified juglones enhanced mammalian pol inhibition and their cytotoxic and anti-inflammatory activities. The juglone conjugated with oleic acid (C18:1-acyl juglone) showed the strongest inhibition of DNA replicative pol alpha activity and human colon carcinoma (HCT116) cell growth in 10 synthesized 5-O-acyl juglones. C12:0-Acyl juglone was the strongest inhibitor of DNA repair-related pot lambda, as well as the strongest suppression of the production of tumor necrosis factor (TNF)-alpha production induced by lipopolysaccharide (LPS) in the compounds tested. Moreover, this compound caused the greatest reduction in 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced acute inflammation in mouse ears. C12:0- and C18:1-Acyl juglones selectively inhibited the activities of mammalian pol species, but did not influence the activities of other pols and DNA metabolic enzymes tested. These data indicate that the novel 5-O-acyl juglones target anti-cancer and/or anti-inflammatory agents based on mammalian pot inhibition. Moreover, the results suggest that acylation of juglone is an effective chemical modification to improve the anti-cancer and anti-inflammation of vitamin K(3) derivatives, such as juglone. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.
• 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.