2-(acetoxymethyl)-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromene-3,4,8,10-tetrayl tetraacetate | 14531-47-6

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(acetoxymethyl)-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromene-3,4,8,10-tetrayl tetraacetate
• 英文别名: 3,4,8,10,11-penta-O-acetylbergenin；bergenin 3,4,8,10,11-pentaacetate；penta-O-acetyl bergenin；(4aS)-3t,4c,8,10-tetraacetoxy-2c-acetoxymethyl-9-methoxy-(4ar,10bt)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one；(4aS)-3t,4c,8,10-Tetraacetoxy-2c-acetoxymethyl-9-methoxy-(4ar,10bt)-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-on；Bergenin-pentaacetat；Bergenin Pentaacetate；[(2R,3R,4R,4aS,10bS)-3,4,8,10-tetraacetyloxy-9-methoxy-6-oxo-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-2-yl]methyl acetate
• CAS: 14531-47-6
• 化学式: C₂₄H₂₆O₁₄
• 分子量: 538.462
• InChiKey: NCBOXCFFSWALMZ-XTNBEGJDSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  乙酸酐 、 岩白菜素 在 吡啶 作用下， 以83%的产率得到2-(acetoxymethyl)-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromene-3,4,8,10-tetrayl tetraacetate
  参考文献：
  名称：

  佛手柑的结构。

  摘要：

  X射线分析的3,4,8,10,11-乙酸戊酯（3）已证实较早的结构分配。

  DOI：

  10.1016/0008-6215(91)80113-2

文献信息

• Synthesis, pH dependent, plasma and enzymatic stability of bergenin prodrugs for potential use against rheumatoid arthritis
  作者：Rohit Singh、Vikas Kumar、Sonali S. Bharate、Ram A. Vishwakarma

  DOI：10.1016/j.bmc.2017.08.011

  日期：2017.10

  plasma/esterase. The stability of synthesized prodrugs was evaluated in buffers at different pH, in biorelevant media such as SGF, SIF, rat plasma and in esterase enzyme. All prodrugs displayed significantly improved lipophilicity compared with bergenin, which was in accordance with the criteria of drug-like compounds. Acetyl ester 4a2 appeared to be the most promising prodrug as it remained stable at gastric/intestinal

  卑尔根是一个独特的C-糖苷天然产物具有抗炎和抗关节炎活性。它是亲水分子，在酸性条件下稳定，但是在中性碱性pH条件下不稳定。降解速率与pH值增加成正比，这可能是其口服生物利用度低的原因之一。因此，本文的目的是使用前药策略改善其稳定性。合成了各种酯和醚前药，并研究了它们在血浆/酯酶中的亲脂性，化学稳定性和酶促水解作用。在不同pH的缓冲液，生物相关培养基（如SGF，SIF，大鼠血浆和酯酶）中评估了合成前药的稳定性。所有的前药都显示出比bergenin显着改善的亲脂性，这符合类药物化合物的标准。乙酰酯4a 2似乎是最有前途的前药，因为它在胃/肠pH值下保持稳定，并根据理想前药的需要在血浆中完全转化为母体化合物bergenin。本文提供的数据将有助于设计结构相似的化学型中具有所需理化性质的不稳定分子的稳定前药。
• Hasegawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 313,316; engl. Ref. S. 98, 100
  作者：Hasegawa

  DOI：——

  日期：——
• 453. Bergenin, a C-glycopyranosyl derivative of 4-O-methylgallic acid
  作者：J. Evelyn Hay、L. J. Haynes

  DOI：10.1039/jr9580002231

  日期：——
• Murthy, Y. L. N.; Jairaj, M. A., Journal of the Indian Chemical Society, 1988, vol. 65, # 10, p. 738 - 739
  作者：Murthy, Y. L. N.、Jairaj, M. A.

  DOI：——

  日期：——
• Practical Synthesis and Biological Evaluation of Bergenin Analogs
  作者：Jae-Chul Jung、Eunyoung Lim、Seung Hwan Kim、Nam Soo Kim、Mankil Jung、Seikwan Oh

  DOI：10.1111/j.1747-0285.2011.01194.x

  日期：2011.10

  Here, we describe the practical synthesis and biological properties of bergenin and its structural analogs. Synthetic bergenin compounds were prepared by acylation of bergenin. These compounds were then evaluated for suppression of lipopolysaccharide‐induced nitric oxide (NO) generation in cultured cells and anti‐narcotic effects on morphine‐dependent mice. We found that bergenin derivatives showed potent anti‐inflammatory activity (suppression of NO generation) at concentrations ranging from 20 to 30 μmin vitro, and bergenin derivatives (10–20 mg/kg) exhibited significant anti‐narcotic effects on morphine dependence in mice. These results suggest the potential utility of bergenin and its analogs as anti‐narcotic agents and the design of more potent anti‐inflammatory compounds.