cyclobutanecarbonyl-miliusol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclobutanecarbonyl-miliusol
• 英文别名: [(1R,5R,9S)-1-[(1E)-2,6-dimethylhepta-1,5-dienyl]-3,6-dioxo-2-oxaspiro[4.5]dec-7-en-9-yl] cyclobutanecarboxylate
• 化学式: C₂₃H₃₀O₅
• 分子量: 386.488
• InChiKey: SRNCFCHGNBPWES-QGZBLNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  9β-hydroxy-1β-(E-2,6-dimethylhepta-1,5-dienyl)-2-oxa-spiro[4.5]dec-7-ene-3,6-dione 、 环丁基甲酰氯 在 吡啶 作用下， 反应 18.0h， 以52.5%的产率得到cyclobutanecarbonyl-miliusol
  参考文献：
  名称：

  Miliusanes, A Class of Cytotoxic Agents from Miliusa sinensis

  摘要：

  Bioassay-directed fractionation of the leaves, twigs, and flowers of Miliusa sinensis Finet and Gagnep. (Annonaceae) led to the isolation of a new class of potential anticancer lead molecules. They are a cluster of compounds composed of a C-18 carbon skeleton, a known but heretofore unnamed type, which we have designated as miliusane. Two known (1 and 2) as well as 20 new miliusanes (3-22) have been isolated and identified. They belong to two substructural classes of miliusanes. One subclass (1-19) was determined to be composed of a gamma-lactone spiro-ring system, the opening of which led to the second group of compounds (21 and 22) containing a tetrahydrofuran ring system. Compounds 1-3, 5, 8, 9, 18, 20, and 21 demonstrated significant cytotoxic activity in our cancer cell line panel comprising KB, Col-2, LNCaP, Lu-1, MCF-7, and HUVEC. The structures were determined by spectroscopic and chemical methods. The structure of miliusate was further confirmed by X-ray crystallographic analysis. The absolute stereochemistry of miliusanes was established by the Mosher ester method. Forty-two modified miliusane derivatives were also prepared and evaluated for their cytotoxic activities.

  DOI：

  10.1021/jm0509492

文献信息

• Miliusanes, A Class of Cytotoxic Agents from <i>Miliusa sinensis</i>
  作者：Hong-Jie Zhang、Cuiying Ma、Nguyen Van Hung、Nguyen Manh Cuong、Ghee Teng Tan、Bernard D. Santarsiero、Andrew D. Mesecar、D. Doel Soejarto、John M. Pezzuto、Harry H. S. Fong

  DOI：10.1021/jm0509492

  日期：2006.1.1

  Bioassay-directed fractionation of the leaves, twigs, and flowers of Miliusa sinensis Finet and Gagnep. (Annonaceae) led to the isolation of a new class of potential anticancer lead molecules. They are a cluster of compounds composed of a C-18 carbon skeleton, a known but heretofore unnamed type, which we have designated as miliusane. Two known (1 and 2) as well as 20 new miliusanes (3-22) have been isolated and identified. They belong to two substructural classes of miliusanes. One subclass (1-19) was determined to be composed of a gamma-lactone spiro-ring system, the opening of which led to the second group of compounds (21 and 22) containing a tetrahydrofuran ring system. Compounds 1-3, 5, 8, 9, 18, 20, and 21 demonstrated significant cytotoxic activity in our cancer cell line panel comprising KB, Col-2, LNCaP, Lu-1, MCF-7, and HUVEC. The structures were determined by spectroscopic and chemical methods. The structure of miliusate was further confirmed by X-ray crystallographic analysis. The absolute stereochemistry of miliusanes was established by the Mosher ester method. Forty-two modified miliusane derivatives were also prepared and evaluated for their cytotoxic activities.