methyl tri-O-methylbrevifolincarboxylate | 109155-54-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: methyl tri-O-methylbrevifolincarboxylate
• 英文别名: 7,8,9-trimethoxy-3,5-dioxo-1,2,3,5-tetrahydro-cyclopent[c]isochromene-1-carboxylic acid methyl ester；7,8,9-Trimethoxy-3,5-dioxo-1,2,3,5-tetrahydro-cyclopent[c]isochromen-1-carbonsaeure-methylester；methyl 7,8,9-trimethoxy-3,5-dioxo-1,2-dihydrocyclopenta[c]isochromene-1-carboxylate
• CAS: 109155-54-6
• 化学式: C₁₇H₁₆O₈
• 分子量: 348.309
• InChiKey: CYSWQMCNLSLKBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101.27
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 alkaline earth salt of/the/ methylsulfuric acid 在 甲醇 、 乙醚 作用下， 生成 methyl tri-O-methylbrevifolincarboxylate
  参考文献：
  名称：

  Schmidt; Bernauer, Justus Liebigs Annalen der Chemie, 1954, vol. 588, p. 211,221

  摘要：

  DOI：

文献信息

• Tannins and Related Polyphenols of Euphorbiaceous Plants. IX. Hydrolyzable Tannins with 1C4 Glucose Core from Phyllanthus flexuosus MUELL. ARG.
  作者：Takashi YOSHIDA、Hideyuki ITOH、Shunyo MATSUNAGA、Reiko TANAKA、Takuo OKUDA

  DOI：10.1248/cpb.40.53

  日期：——

  Four new hydrolyzable tannins (phyllanthusiins A-D), a new polyphenol of related structure (phyllanthusiin E), and eight known polyphenols have been isolated from the leaves of Phyllanthus flexuosus. On the basis of the spectroscopic methods including 1H-13C long-range two-dimensional nuclear magnetic resonance techniques, phyllanthusiins A (9), B (12) and C(14), were characterized as oxidative metabolites of geraniin, each having a different new acyl group biogenetically formed via an oxidative cleavage of the dehydrohexahydroxydiphenoyl group, on the 1C4 glucopyranose core. Phyllanthusiin D (15) was determined to be a condensate of geraniin with acetone, and phyllanthusiin E (16), was an oxidized congener of ellagic acid.

  从蛇菰（Phyllanthus flexuosus）的叶子中分离出了四种新的可水解单宁（Phyllanthusiins A-D）、一种相关结构的新型多酚（Phyllanthusiin E）以及八种已知多酚。根据包括1H-13C长程二维核磁共振技术在内的光谱学方法，Phyllanthusiins A（9）、B（12）和C（14）被鉴定为-geraniin的氧化代谢产物，每种都具有不同的新酰基，通过对去氢六羟基二苯酰基（dehydrohexahydroxydiphenoyl）基团的氧化裂解，在1C4葡萄糖吡喃核心上生成。Phyllanthusiin D（15）被确定为geraniin与丙酮的缩合物，而Phyllanthusiin E（16）则是鞣酸的氧化同类物。
• YOSHIDA, TAKASHI;JIN, ZHE-XIONG;OKUDA, TAKUO, CHEM. AND PHARM. BULL., 39,(1991) N, C. 49-54
  作者：YOSHIDA, TAKASHI、JIN, ZHE-XIONG、OKUDA, TAKUO

  DOI：——

  日期：——
• Selective inactivation of triosephosphate isomerase from Trypanosoma cruzi by brevifolin carboxylate derivatives isolated from Geranium bellum Rose
  作者：Juan Gayosso-De-Lucio、Martin Torres-Valencia、Arturo Rojo-Domínguez、Hugo Nájera-Peña、Beatriz Aguirre-López、José Salas-Pacheco、Claudia Avitia-Domínguez、Alfredo Téllez-Valencia

  DOI：10.1016/j.bmcl.2009.08.055

  日期：2009.10

  In the search of molecules that can serve as leads in the design of a new drug for the treatment of Chagas' disease, we found that some brevifolin carboxylate derivatives isolated from Geranium bellum Rose, inactivate triosephosphate isomerase from Trypanosoma cruzi (TcTIM) in a species-specific manner. After spectroscopic characterization, these compounds were identified as methylbrevifolin carboxylate (1), ethylbrevifolin carboxylate (2), butylbrevifolin carboxylate (3) and the methylated derivate methyl tri-O-methylbrevifolin carboxylate (4). The concentrations required to inactivate fifty percent the activity of TcTIM were 6.5, 8 and 14 mu M of 1, 2 and 3, respectively, while compound 4 had no inhibitory effect. Molecular docking simulations of 1 on the structure of TcTIM showed that residues of both monomers interact with the compound. These compounds are very selective with respect to the parasite enzyme, since they showed no effect on the activity of human TIM at concentrations as high as 1 mM. In conclusion, the brevifolin carboxylate derivatives described here are excellent leads in the search of a new chemotherapy for the treatment of this disease. (C) 2009 Elsevier Ltd. All rights reserved.