juglone myristate | 64817-83-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: juglone myristate
• 英文别名: Myristoyljuglon；Myristoyljuglone；(5,8-dioxonaphthalen-1-yl) tetradecanoate
• CAS: 64817-83-0
• 化学式: C₂₄H₃₂O₄
• 分子量: 384.516
• InChiKey: MLHGIEIXYMQFHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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 、 肉豆蔻酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 生成 juglone myristate
  参考文献：
  名称：

  蒽醌（1,8-二羟基-9-蒽酮）类似物的结构和促肿瘤活性。

  摘要：

  在单次应用亚致癌剂量的7,12-二甲基苯并[蒽]蒽后，通过使用雌性ICR / Ha Swiss小鼠在小鼠皮肤上重复皮肤应用，测试了肿瘤促进剂anthralin的17种类似物的相同生物学特性。测试的化合物中有七个是新化合物。它们是1,8-二乙酰氧基-9-蒽酮，1,8-二肉豆蔻酰氧基-9-蒽酮，1,8-二羟基-10-乙酰基-9-蒽酮，1,8-二羟基-10-肉豆蔻酰基-9-蒽酮， 1,8,10-三羟基-9-蒽酮，1,8-二羟基-9,10-二氢蒽和肉豆蔻酰juglone。所有化合物均以纯净形式用于生物测定。在17种测试化合物中，有4种显示出明显的促肿瘤活性。它们是1,8-二羟基-10-乙酰基-9-蒽酮，1,8-二羟基-10-肉豆蔻酰基-9-蒽酮，1-羟基-9-蒽酮和juglone。为了确定在该系列中促进肿瘤的活性与金属螯合之间是否存在任何关系，使用二价金属离子Cu（II），Zn（）检测了蒽林及其非活性类似物1

  DOI：

  10.1021/jm00199a005

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。
• Structure and tumor-promoting activity of analogs of anthralin (1,8-dihydroxy-9-anthrone)
  作者：B. L. Van Duuren、A. Segal、S. S. Tseng、G. M. Rusch、G. Loewengart、U. Mate、D. Roth、A. Smith、S. Melchionne、I. Seidman

  DOI：10.1021/jm00199a005

  日期：1978.1

  10-dihydroanthracene, and myristoyljuglone. All compounds were used in pure form for the bioassays. Of the 17 test compounds four showed notable tumor-promoting activity. They are 1,8-dihydroxy-10-acetyl-9-anthrone, 1,8-dihydroxy-10-myristoyl-9-anthrone, 1-hydroxy-9-anthrone, and juglone. In order to determine whether there is any relationship between tumor-promoting activity and metal chelation in this series

  在单次应用亚致癌剂量的7,12-二甲基苯并[蒽]蒽后，通过使用雌性ICR / Ha Swiss小鼠在小鼠皮肤上重复皮肤应用，测试了肿瘤促进剂anthralin的17种类似物的相同生物学特性。测试的化合物中有七个是新化合物。它们是1,8-二乙酰氧基-9-蒽酮，1,8-二肉豆蔻酰氧基-9-蒽酮，1,8-二羟基-10-乙酰基-9-蒽酮，1,8-二羟基-10-肉豆蔻酰基-9-蒽酮， 1,8,10-三羟基-9-蒽酮，1,8-二羟基-9,10-二氢蒽和肉豆蔻酰juglone。所有化合物均以纯净形式用于生物测定。在17种测试化合物中，有4种显示出明显的促肿瘤活性。它们是1,8-二羟基-10-乙酰基-9-蒽酮，1,8-二羟基-10-肉豆蔻酰基-9-蒽酮，1-羟基-9-蒽酮和juglone。为了确定在该系列中促进肿瘤的活性与金属螯合之间是否存在任何关系，使用二价金属离子Cu（II），Zn（）检测了蒽林及其非活性类似物1
• 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.