methyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate | 5038-46-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: methyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate
• 英文别名: methyl 4-O-demethylbarbatate；metyl 4-O-demethylbarbatate；4-(2,4-dihydroxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester；4-(2,4-Dihydroxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoesaeure-methylester；4-O-Desmethylbarbatinsaeuremethylester；4-O-Demethylbarbatsaeuremethylester；(3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 2,4-dihydroxy-3,6-dimethylbenzoate
• CAS: 5038-46-0
• 化学式: C₁₉H₂₀O₇
• 分子量: 360.364
• InChiKey: ODMVDRJFBPXTRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,4-dihydroxy-3,6-dimethylbenzaldehyde 在 吡啶 、 sodium hydroxide 、 potassium permanganate 、 氯化亚砜 、 乙醚 、 magnesium sulfate 、 丙酮 作用下， 生成 methyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate
  参考文献：
  名称：

  Fujikawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1936, vol. 56, p. 237,245; dtsch. Ref. S. 25, 27

  摘要：

  DOI：

文献信息

• Depsides: Lichen Metabolites Active against Hepatitis C Virus
  作者：Thi Huyen Vu、Anne-Cécile Le Lamer、Claudia Lalli、Joël Boustie、Michel Samson、Françoise Lohézic-Le Dévéhat、Jacques Le Seyec

  DOI：10.1371/journal.pone.0120405

  日期：——

  A thorough phytochemical study of Stereocaulon evolutum was conducted, for the isolation of structurally related atranorin derivatives. Indeed, pilot experiments suggested that atranorin (1), the main metabolite of this lichen, would interfere with the lifecycle of hepatitis C virus (HCV). Eight compounds, including one reported for the first time (2), were isolated and characterized. Two analogs (5, 6) were also synthesized, to enlarge the panel of atranorin-related structures. Most of these compounds were active against HCV, with a half-maximal inhibitory concentration of about 10 to 70 µM, with depsides more potent than monoaromatic phenols. The most effective inhibitors (1, 5 and 6) were then added at different steps of the HCV lifecycle. Interestingly, atranorin (1), bearing an aldehyde function at C-3, inhibited only viral entry, whereas the synthetic compounds 5 and 6, bearing a hydroxymethyl and a methyl function, respectively, at C-3 interfered with viral replication.

  我们对 Stereocaulon evolutum 进行了深入的植物化学研究，以分离出结构相关的阿曲霉毒素衍生物。事实上，先导实验表明，这种地衣的主要代谢产物阿曲霉素（1）会干扰丙型肝炎病毒（HCV）的生命周期。研究人员分离并鉴定了八种化合物，包括一种首次报道的化合物（2）。此外，还合成了两种类似物（5、6），以扩大阿特拉诺林相关结构的研究范围。这些化合物大多对 HCV 有活性，半数最大抑制浓度约为 10 至 70 µM，其中苷类的作用比单芳香族酚类更强。最有效的抑制剂（1、5 和 6）随后被添加到 HCV 生命周期的不同阶段。有趣的是，C-3 处具有醛功能的阿曲霉素（1）只抑制病毒的进入，而 C-3 处分别具有羟甲基和甲基功能的合成化合物 5 和 6 则干扰病毒的复制。
• Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid
  作者：Sunil Kumar KC、Klaus Müller

  DOI：10.1016/s0223-5234(99)00132-4

  日期：1999.12

  A series of barbatic and diffractaic acid analogues has been synthesized and evaluated as inhibitors of leukotriene B-4 (LTB4) biosynthesis and as antiproliferative agents. The 4-O-demethyl barbatic and diffractaic acid derivatives were among the most active compounds in both assays. In particular, ethyl 4-O-demethylbarbatate was the most potent LTB4 biosynthesis inhibitor of this series, with an IC50 value in the submicromolar range. Because the compounds did not show appreciable reactivity against a stable free radical, 2,2-diphenyl-1-picrylhydrazyl, and did not produce appreciable amounts of deoxyribose degradation as a measure of their potency to generate hydroxyl radicals, a simple redox effect could not explain their biological activity. Also, there was no nonspecific cytotoxicity as documented by the activity of lactate dehydrogenase released from the cytoplasm of keratinocytes, which was in the control range. (C) 1999 Editions scientifiques et medicales Elsevier SAS.
• In the arms of morpheus: the development of morphine for postoperative pain relief
  作者：Gillian R. Hamilton、Thomas F. BAskett

  DOI：10.1007/bf03020955

  日期：2000.4

  Purpose: To analyse the historical development of morphine for postoperative analgesia and how this development was shaped by the evolution of anesthetic techniques.Methods: After a systematic review of the literature, information was gathered from primary sources.Principal Findings: in ancient medicine, some plant derivatives were used to alleviate pain including: alcohol, cannabis, mandrake, and opium. Over the past two centuries, opium and its derivatives have become the most widely used analgesics for severe pain. Before the development of general anesthesia, surgery was only performed out of extreme necessity. It is probable that an analgesic such as opium would have been given following surgery although its use may not have been recorded. The first description of postoperative opium was by James Moore in 1784, Morphine was isolated from opium by Friedrich Serturner in 1805. However, it was not until the development of the hypodermic needle and syringe nearly 50 yr later that the use of morphine became widespread. Over the last century, various delivery systems for morphine have been developed including sub-arachanoid and epidural injection, and more recently patient-controlled intravenous, epidural and intranasal analgesia. In addition, many new opioids have been synthesized.Conclusion: Since its isolation from opium almost 200 yr ago, morphine remains the most widely used analgesic and the standard against which all new opioids for postoperative pain relief are compared.
• Elix, John A.; Mahadevan, Indu; Wardlaw, Judith H., Australian Journal of Chemistry, 1987, vol. 40, # 9, p. 1581 - 1590
  作者：Elix, John A.、Mahadevan, Indu、Wardlaw, Judith H.、Arvidsson, Lars、Joergensen, Per Magnus

  DOI：——

  日期：——
• ELIX, JONN A.;MANADEVAN, INDU;WARDLAW, JUDITN N.;ARVIDSSON, LARS;JZHUSTOO+, AUSTRAL. J. CHEM., 40,(1987) N 9, 1581-1590
  作者：ELIX, JONN A.、MANADEVAN, INDU、WARDLAW, JUDITN N.、ARVIDSSON, LARS、JZHUSTOO+

  DOI：——

  日期：——