p-iodophenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside | 596847-04-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-iodophenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,5-diacetyloxy-6-(4-iodophenoxy)-4-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 596847-04-0
• 化学式: C₂₁H₂₅IO₉
• 分子量: 548.329
• InChiKey: AXXTVHJJZHZYHJ-YMQHIKHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  p-iodophenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 在 吡啶 、 甲醇 、 tetrafluoroboric acid 、 sodium methylate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 p-iodophenyl 3-O-allyl-4,6-O-benzylidene-2-O-propionyl-β-D-glucopyranoside
  参考文献：
  名称：

  Functionalized Glycomers as Growth Inhibitors and Inducers of Apoptosis in Human Glioblastoma Cells

  摘要：

  The effects of functionalized aryl beta-D-glycopyranosides (glycomers) on the proliferation, survival, and apoptosis of human glioblastoma cells in culture were evaluated as a way to control tumor progression. The results showed that inhibition of growth and/or induction of apoptosis can be achieved by these molecules in human glioblastoma cells. Inhibition of DNA synthesis precedes induction of apoptosis and growth inhibition. The substituents at C-1, C-2, C-3,C-4, and C-6 on the pyranosidic scaffold are important to modulate the action and the efficacy of these molecules. Human fibroblasts and brain-derived endothelial cells were less sensitive to glycomers than tumor cells. Thus, functionalized aryl beta-D-glycopyranosides represent a new class of molecules potentially able to control the progression of brain tumors.

  DOI：

  10.1021/jm0205853
• 作为产物：
  描述：

  1,2,4,6-四-O-乙酰基-3-O-烯丙基-β-D-吡喃葡萄糖 在 氢溴酸 、 四氯化锡 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 p-iodophenyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside
  参考文献：
  名称：

  Functionalized Glycomers as Growth Inhibitors and Inducers of Apoptosis in Human Glioblastoma Cells

  摘要：

  The effects of functionalized aryl beta-D-glycopyranosides (glycomers) on the proliferation, survival, and apoptosis of human glioblastoma cells in culture were evaluated as a way to control tumor progression. The results showed that inhibition of growth and/or induction of apoptosis can be achieved by these molecules in human glioblastoma cells. Inhibition of DNA synthesis precedes induction of apoptosis and growth inhibition. The substituents at C-1, C-2, C-3,C-4, and C-6 on the pyranosidic scaffold are important to modulate the action and the efficacy of these molecules. Human fibroblasts and brain-derived endothelial cells were less sensitive to glycomers than tumor cells. Thus, functionalized aryl beta-D-glycopyranosides represent a new class of molecules potentially able to control the progression of brain tumors.

  DOI：

  10.1021/jm0205853

文献信息

• Design and synthesis of functionalized glycomers as non-peptidic ligands for SH2 binding and as inhibitors of A-431 human epidermoid and HT-29 colon carcinoma cell lines
  作者：Stephen Hanessian、Oscar M. Saavedra、Fang Xie、Nadia Amboldi、Carlo Battistini

  DOI：10.1016/s0960-894x(00)00022-6

  日期：2000.3

  A set of O-subsiitutsd aryl beta-D-glucopyranosides were prepared and found to have inhibitory activity on the growth of two carcinona cell lines. (C) 2000 Elsevier Science Ltd. All rights reserved.