n-propyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate | 261174-60-1

• 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: n-propyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate
• 英文别名: (3-Hydroxy-2,5-dimethyl-4-propoxycarbonylphenyl) 2-hydroxy-3,6-dimethyl-4-phenylmethoxybenzoate
• CAS: 261174-60-1
• 化学式: C₂₈H₃₀O₇
• 分子量: 478.542
• InChiKey: JVUTXQMLCZRBSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  n-propyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以90%的产率得到n-propyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate
  参考文献：
  名称：

  Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(99)00132-4
• 作为产物：
  描述：

  ethyl 2,4-dihydroxy-3,6-dimethylbenzoate 在 氢氧化钾 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 24.0h， 生成 n-propyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate
  参考文献：
  名称：

  Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid

  摘要：

  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.

  DOI：

  10.1016/s0223-5234(99)00132-4

文献信息

• Semisynthesis, Biological Evaluation and Molecular Docking Studies of Barbatic Acid Derivatives as Novel Diuretic Candidates
  作者：Xiang Yu、Yi Sui、Yinkai Xi、Yan Zhang、Guoyong Luo、Yi Long、Wude Yang

  DOI：10.3390/molecules28104010

  日期：——

  variety of biological activities. In this study, a series of esters based on barbatic acid (6a–q′) were designed, synthesized, and evaluated for their diuretic and litholytic activity at a concentration of 100 μmol/L in vitro. All target compounds were characterized using 1H NMR, 13C NMR, and HRMS, and the spatial structure of compound 6w was confirmed using X-ray crystallography. The biological results

  Barbatic acid 是一种从地衣中分离出来的化合物，具有多种生物活性。在这项研究中，设计、合成了一系列基于半巴巴酸 (6a–q') 的酯类，并评估了它们在 100 μmol/L 浓度下的体外利尿和溶石活性。使用 1H NMR、13C NMR 和 HRMS 对所有目标化合物进行了表征，并使用 X 射线晶体学确认了化合物 6w 的空间结构。生物学结果表明，包括 6c、6b' 和 6f' 在内的一些衍生物表现出强大的利尿活性，而 6j 和 6m 则表现出良好的溶石活性。分子对接研究进一步表明，6b' 与利尿相关的 WNK1 激酶具有最佳结合亲和力，而 6j 可以通过多种力量与碳酸氢盐转运蛋白 CaSR 结合。