4-Retinamidophenyl-β-D-glucopyranoside

• 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: 4-Retinamidophenyl-β-D-glucopyranoside
• 英文别名: (2E,4E,6E,8E)-3,7-dimethyl-N-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
• 化学式: C₃₂H₄₃NO₇
• 分子量: 553.696
• InChiKey: BDODYAROMXLLAI-DARQXHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 palladium dihydroxide 4-二甲氨基吡啶 、 bismuth(III) bromide 、 三甲基溴硅烷 、 氨 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 51.33h， 生成 4-Retinamidophenyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide

  摘要：

  Three glycosyl (glucosyl, galactosyl, mannosyl) conjugates of 4-hydroxyphenylretinamide have been synthesized and tested on a broad variety of tumor cells. All three compounds are active on promyelocytic leukemia cell lines HL60 but less than the parent compound 4-HPR. Among them, the mannosyl analog stands out by its very low toxicity. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01074-6

文献信息

• Synthesis and biological activity of glycosyl conjugates of N-(4-hydroxyphenyl)retinamide
  作者：Jean-Yves Winum、Alain Leydet、Michel Seman、Jean-Louis Montero

  DOI：10.1016/s0014-827x(01)01074-6

  日期：2001.4

  Three glycosyl (glucosyl, galactosyl, mannosyl) conjugates of 4-hydroxyphenylretinamide have been synthesized and tested on a broad variety of tumor cells. All three compounds are active on promyelocytic leukemia cell lines HL60 but less than the parent compound 4-HPR. Among them, the mannosyl analog stands out by its very low toxicity. (C) 2001 Elsevier Science S.A. All rights reserved.