cleistetroside-new-1 | 1415255-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cleistetroside-new-1
• 英文别名: [(2S,3S,4S,5R,6S)-4-[(2S,3R,4R,5S,6S)-3-acetyloxy-5-hydroxy-6-methyl-4-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6-[(2S,3R,4S,5R,6R)-6-dodecoxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-5-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 1415255-44-5
• 化学式: C₄₆H₇₆O₂₂
• 分子量: 981.096
• InChiKey: OLMAIRVUORQWBM-IPWJGJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  68
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  286
• 氢给体数：
  4
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  tert-butyl ((2S,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl) carbonate 在 吡啶 、 原乙酸三甲酯 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 四丁基碘化铵 、 二正丁基氧化锡 、 碳酸氢钠 、 对甲苯磺酸 、 溶剂黄146 、 N-甲基吗啉氧化物 、 硫脲 、 三苯基膦 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 64.67h， 生成 cleistetroside-new-1
  参考文献：
  名称：

  Structure–Activity Relationship Study of the Cleistriosides and Cleistetrosides for Antibacterial/Anticancer Activity

  摘要：

  Two known cleistriosides and six known cleistetrosides were synthesized and evaluated for anticancer and antibacterial activities. This study, for the first time, reports anticancer activity and comprehensively the antibacterial activity for these oligosaccharide natural products. In addition, two new unnatural cleistetroside analogues were synthesized and tested. Biological activities for the 10 oligosaccharides against B. subtilis were found to range between 4 and >64 mu M and for NCI-H460 human lung cancer epithelial cells between 7.5 and 90.9 mu M. Similar activities were found for seven of the oligosaccharides against the NCI panel of 60 cell lines. The degree of acylation and location of the specific acetate groups had significant effects on the anticancer and antibacterial activity of both the cleistriosides and the cleistetrosides.

  DOI：

  10.1021/ml300303g