O-tert-butyl-N-(4-methylbenzyl)-N-(D-glucosyl)-hydroxylamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-tert-butyl-N-(4-methylbenzyl)-N-(D-glucosyl)-hydroxylamine
• 化学式: C₁₈H₂₉NO₆
• 分子量: 355.431
• InChiKey: LYKBLSPHJAVSRL-VDWCLKJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  102.62
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  O-tert-butyl-N-(4-methylbenzyl)-N-(D-glucosyl)-hydroxylamine 在 水 作用下， 以 二甲基亚砜 为溶剂， 反应 60.0h， 生成 可得然胶 、 O-tert-butyl-N-(4-methylbenzyl)hydroxylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of RON-neoglycosides as tumor cytotoxins

  摘要：

  Cardenolides such as digitoxin have been shown to inhibit cancer cell growth, to reduce cancer metastasis, and to induce apoptosis in tumor cells. Among the most potent digitoxin-based cytotoxins identified to date are MeON-neoglycosides generated via oxyamine neoglycosylation. Here, we report our studies of oxyamine neoglycosylation aimed at facilitating the elucidation of linkage-diversified digitoxin neoglycoside structure-activity relationships. We identified conditions suitable for the convenient synthesis of digitoxin neoglycosides and found that sugar structure, rather than RON-glycosidic linkage, exerts the strongest influence on neoglycoside yield and stereochemistry. We synthesized a library of digitoxin neoglycosides and assessed their cytotoxicity against eight human cancer cell lines. Consistent with previous findings, our data show that the structure of RON-neoglycosidic linkages influences both the potency and selectivity of digitoxin neoglycosides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.019
• 作为产物：
  描述：

  在 盐酸 、 硼烷-三甲胺络合物 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 54.0h， 生成 O-tert-butyl-N-(4-methylbenzyl)-N-(D-glucosyl)-hydroxylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of RON-neoglycosides as tumor cytotoxins

  摘要：

  Cardenolides such as digitoxin have been shown to inhibit cancer cell growth, to reduce cancer metastasis, and to induce apoptosis in tumor cells. Among the most potent digitoxin-based cytotoxins identified to date are MeON-neoglycosides generated via oxyamine neoglycosylation. Here, we report our studies of oxyamine neoglycosylation aimed at facilitating the elucidation of linkage-diversified digitoxin neoglycoside structure-activity relationships. We identified conditions suitable for the convenient synthesis of digitoxin neoglycosides and found that sugar structure, rather than RON-glycosidic linkage, exerts the strongest influence on neoglycoside yield and stereochemistry. We synthesized a library of digitoxin neoglycosides and assessed their cytotoxicity against eight human cancer cell lines. Consistent with previous findings, our data show that the structure of RON-neoglycosidic linkages influences both the potency and selectivity of digitoxin neoglycosides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.019

文献信息

• Synthesis and biological evaluation of RON-neoglycosides as tumor cytotoxins
  作者：Joseph M. Langenhan、Matthew M. Endo、Jeffrey M. Engle、Liane L. Fukumoto、Derek R. Rogalsky、Lauren K. Slevin、Lindsay R. Fay、Ryan W. Lucker、James R. Rohlfing、Kyle R. Smith、Anja E. Tjaden、Halina M. Werner

  DOI：10.1016/j.carres.2011.09.019

  日期：2011.12

  Cardenolides such as digitoxin have been shown to inhibit cancer cell growth, to reduce cancer metastasis, and to induce apoptosis in tumor cells. Among the most potent digitoxin-based cytotoxins identified to date are MeON-neoglycosides generated via oxyamine neoglycosylation. Here, we report our studies of oxyamine neoglycosylation aimed at facilitating the elucidation of linkage-diversified digitoxin neoglycoside structure-activity relationships. We identified conditions suitable for the convenient synthesis of digitoxin neoglycosides and found that sugar structure, rather than RON-glycosidic linkage, exerts the strongest influence on neoglycoside yield and stereochemistry. We synthesized a library of digitoxin neoglycosides and assessed their cytotoxicity against eight human cancer cell lines. Consistent with previous findings, our data show that the structure of RON-neoglycosidic linkages influences both the potency and selectivity of digitoxin neoglycosides. (C) 2011 Elsevier Ltd. All rights reserved.