8-hydroxy-3-methoxy-11-oxo-1-pentanoyl-6-pentyl-11H-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid methyl ester | 20661-49-8

• 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: 8-hydroxy-3-methoxy-11-oxo-1-pentanoyl-6-pentyl-11H-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid methyl ester
• 英文别名: 8-hydroxy-3-methoxy-11-oxo-6-pentyl-1-valeryl-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid methyl ester；8-Hydroxy-3-methoxy-11-oxo-6-pentyl-1-valeryl-11H-dibenzo[b,e][1,4]dioxepin-7-carbonsaeure-methylester；Methyl 3-hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylate
• CAS: 20661-49-8
• 化学式: C₂₆H₃₀O₈
• 分子量: 470.519
• InChiKey: XQTRWYHOGMCUKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  肺衣酸 、 三甲基硅烷化重氮甲烷 在 吡啶 作用下， 生成 8-hydroxy-3-methoxy-11-oxo-1-pentanoyl-6-pentyl-11H-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid methyl ester
  参考文献：
  名称：

  柠檬酸和一种新的苯并呋喃，Sasarecaulon sasakii的sakisacaulon A的抗有丝分裂活性

  摘要：

  Lobaric酸（1）已被从地衣中分离，Stereocaulon纹枯病用新的苯并呋喃一起，sakisacaulon A（2）。肺酸（1）抑制微管蛋白的聚合。讨论了叶酸及其衍生物对微管蛋白聚合抑制活性的构效关系。

  DOI：

  10.1016/j.bmcl.2009.03.170

文献信息

• Antimitotic activity of lobaric acid and a new benzofuran, sakisacaulon A from Stereocaulon sasakii
  作者：Hiroshi Morita、Tomoe Tsuchiya、Koji Kishibe、Sayaka Noya、Motoo Shiro、Yusuke Hirasawa

  DOI：10.1016/j.bmcl.2009.03.170

  日期：2009.7

  Lobaric acid (1) has been isolated from lichen, Stereocaulon sasakii together with a new benzofuran, sakisacaulon A (2). Lobaric acid (1) inhibited the polymerization of tubulin. Structure–activity relationship of lobaric acid and its derivatives on inhibitory activity of tubulin polymerization was discussed.

  Lobaric酸（1）已被从地衣中分离，Stereocaulon纹枯病用新的苯并呋喃一起，sakisacaulon A（2）。肺酸（1）抑制微管蛋白的聚合。讨论了叶酸及其衍生物对微管蛋白聚合抑制活性的构效关系。
• Asahina; Nonomura, Chemische Berichte, 1935, vol. 68, p. 1698,1701
  作者：Asahina、Nonomura

  DOI：——

  日期：——
• Protein tyrosine phosphatase 1B inhibitory effects of depsidone and pseudodepsidone metabolites from the Antarctic lichen Stereocaulon alpinum
  作者：Changon Seo、Jae Hak Sohn、Jong Seog Ahn、Joung Han Yim、Hong Kum Lee、Hyuncheol Oh

  DOI：10.1016/j.bmcl.2009.03.108

  日期：2009.5

  Seven phenolic lichen metabolites (1-7) have been isolated from a methanol extract of the Antarctic lichen Stereocaulon alpinum by various chromatographic methods. The structures of these compounds were determined mainly by analysis of NMR spectroscopic data. A depsidone-type compound, lobaric acid (1) and two pseudodepsidone-type compounds, 2 and 3, exhibited potent inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 0.87 mu M, 6.86 mu M, and 2.48 mu M, respectively. Kinetic analyses of PTP1B inhibition by compounds 1 and 2 suggested that these compounds inhibited PTP1B activity in a non-competitive manner. (C) 2009 Elsevier Ltd. All rights reserved.