(1S,4S,5S,6R,7R,8S,9R,10S)-1,6,8-triacetoxy-4,9-dihydroxy-dihydro-β-agarofuran | 1304779-46-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,4S,5S,6R,7R,8S,9R,10S)-1,6,8-triacetoxy-4,9-dihydroxy-dihydro-β-agarofuran
• 英文别名: [(1S,2S,5S,6R,7R,8S,9R,12R)-8,12-diacetyloxy-2,7-dihydroxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecan-5-yl] acetate
• CAS: 1304779-46-1
• 化学式: C₂₁H₃₂O₉
• 分子量: 428.48
• InChiKey: AABFKSBKMOPMPR-HTFIHRAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-acetoxy-9-benzoyloxy-8-trans-cinnamoyloxy-4,6-dihydroxy-dihydro-β-agarofuran 在 甲醇 、 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 49.0h， 生成 (1S,4S,5S,6R,7R,8S,9R,10S)-1,6,8-triacetoxy-4,9-dihydroxy-dihydro-β-agarofuran 、 (1S,4S,5S,6R,7R,8S,9R,10S)-1,6,8,9-tetra-acetoxy-4-hydroxy-dihydro-β-agarofuran
  参考文献：
  名称：

  Dihydro-β-agarofuran sesquiterpenes isolated from Celastrus vulcanicola as potential anti-Mycobacterium tuberculosis multidrug-resistant agents

  摘要：

  In the present study, we report four new dihydro-beta-agarofuran sesquiterpenes (1-4), which were isolated from the leaves of Celastrus vulcanicola, in addition to five derivatives (5-9). Their stereostructures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques, X-ray studies, chemical correlations and biogenetic means. Compounds 1-9 and the previously reported sesquiterpenes 10-25 have been tested as potential antimycobacterial agents against sensitive and resistant Mycobacterium tuberculosis strains. 1 alpha-Acetoxy-6 beta,9 beta-dibenzoyloxy-dihydro-beta-agarofuran (20) exhibited antituberculosis activity against the MDR TB strain with a MIC value of 6.2 mu g/mL, comparable to or better than isoniazid or rifampin, two of the best first-line drugs commonly used in the treatment of TB. The structure-activity relationship is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.02.034

文献信息

• Dihydro-β-agarofuran sesquiterpenes isolated from Celastrus vulcanicola as potential anti-Mycobacterium tuberculosis multidrug-resistant agents
  作者：David Torres-Romero、Ignacio A. Jiménez、Rosario Rojas、Robert H. Gilman、Matías López、Isabel L. Bazzocchi

  DOI：10.1016/j.bmc.2011.02.034

  日期：2011.4

  In the present study, we report four new dihydro-beta-agarofuran sesquiterpenes (1-4), which were isolated from the leaves of Celastrus vulcanicola, in addition to five derivatives (5-9). Their stereostructures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques, X-ray studies, chemical correlations and biogenetic means. Compounds 1-9 and the previously reported sesquiterpenes 10-25 have been tested as potential antimycobacterial agents against sensitive and resistant Mycobacterium tuberculosis strains. 1 alpha-Acetoxy-6 beta,9 beta-dibenzoyloxy-dihydro-beta-agarofuran (20) exhibited antituberculosis activity against the MDR TB strain with a MIC value of 6.2 mu g/mL, comparable to or better than isoniazid or rifampin, two of the best first-line drugs commonly used in the treatment of TB. The structure-activity relationship is discussed. (C) 2011 Elsevier Ltd. All rights reserved.