4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester | 81050-84-2

• 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: 4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester
• 英文别名: 6-Hydroxy-4-(4.6-dimethoxy-2.5-dimethyl-benzoyloxy)-2.5-dimethyl-benzoesaeure-methylester；4-(2,4-Dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoesaeure-methylester；Methyl 4-(2,4-dimethoxy-3,6-dimethylbenzoyl)oxy-2-hydroxy-3,6-dimethylbenzoate
• CAS: 81050-84-2
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: WVDQDUDKODKATA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 地弗地衣酸
  参考文献：
  名称：

  地弗地衣酸及其醚作为抗呼吸道合胞病毒剂

  摘要：

  地衣的主要次生代谢物地弗地衣酸对呼吸道合胞病毒 A2 株具有显着的抗病毒作用，EC 50为 4.8 µM，同时对测试细胞系显示出低毒性（CC 50为 221.9 µM）。我们开发了地弗地衣酸羟基衍生物的合成方法，获得了地弗地衣酸及其甲酯和苄酯三个系列的新衍生物。我们注意到，最有前途的化合物是二氢苯甲酯的衍生物，与二氢呋喃甲酯醚或具有羧基的化合物相比，通常发现其具有相同或更低的细胞毒性。这些修饰的组合允许找到一种有前途的化合物：带有吗啉-4-基-乙基取代基的苄基二氢呋喃酯（EC 50 2.1 µM，CC 50 368.5 µM，SI 175）。

  DOI：

  10.1007/s00044-024-03204-4
• 作为产物：
  描述：

  ethyl 2,4-dihydroxy-3,6-dimethylbenzoate 在 sodium methylate 、 三氟乙酸酐 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester
  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

• Asahina; Hashimoto, Chemische Berichte, 1933, vol. 66, p. 641,645
  作者：Asahina、Hashimoto

  DOI：——

  日期：——
• Asahina; Fujikawa, Chemische Berichte, 1932, vol. 65, p. 580,582
  作者：Asahina、Fujikawa

  DOI：——

  日期：——
• GARBARINO, JUAN A.;CHAMY, MARIA C.;GAMBARO, VICENTE;QUILHOT, WANDA;NARANJ+, J. NATUR. PROD., 50,(1987) N 4, 745-747
  作者：GARBARINO, JUAN A.、CHAMY, MARIA C.、GAMBARO, VICENTE、QUILHOT, WANDA、NARANJ+

  DOI：——

  日期：——
• 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.
• Diffractaic acid and its ethers as anti-respiratory syncytial virus agents
  作者：Aleksandr S. Filimonov、Diana U. Ismangulova、Anastasia A. Diveikina、Nina I. Komarova、Olga A. Luzina、Anna A. Shtro、Anastasia V. Galochkina、Yulia V. Nikolaeva、Artem M. Klabukov、Vera Z. Krivitskaya、Nariman F. Salakhutdinov

  DOI：10.1007/s00044-024-03204-4

  日期：2024.4

  metabolite of lichens, diffractaic acid, was found here to exert a significant antiviral action on respiratory syncytial virus strain A2 with a EC50 of 4.8 µM while showing low toxicity to a tested cell line (CC50 of 221.9 µM). We developed methods for the synthesis of derivatives at the hydroxyl group of diffractaic acid and obtained three series of new derivatives: those of diffractaic acid and of its

  地衣的主要次生代谢物地弗地衣酸对呼吸道合胞病毒 A2 株具有显着的抗病毒作用，EC 50为 4.8 µM，同时对测试细胞系显示出低毒性（CC 50为 221.9 µM）。我们开发了地弗地衣酸羟基衍生物的合成方法，获得了地弗地衣酸及其甲酯和苄酯三个系列的新衍生物。我们注意到，最有前途的化合物是二氢苯甲酯的衍生物，与二氢呋喃甲酯醚或具有羧基的化合物相比，通常发现其具有相同或更低的细胞毒性。这些修饰的组合允许找到一种有前途的化合物：带有吗啉-4-基-乙基取代基的苄基二氢呋喃酯（EC 50 2.1 µM，CC 50 368.5 µM，SI 175）。