3β-ethoxyaminodigitoxigenin | 1012079-82-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-ethoxyaminodigitoxigenin
• 英文别名: 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-(ethoxyamino)-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• CAS: 1012079-82-1
• 化学式: C₂₅H₃₉NO₄
• 分子量: 417.589
• InChiKey: IPMIUHXPJBOYIK-WQFRYHCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-ethoxyaminodigitoxigenin 、 L-ribose 在 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 96.0h， 以61%的产率得到4-((3S,5R,8R,9S,10S,13R,14S,17R)-3-(ethoxy((3S,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)amino)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
  参考文献：
  名称：

  Modifying the glycosidic linkage in digitoxin analogs provides selective cytotoxins

  摘要：

  A chemoselective reaction between oxyamines and unprotected, unactivated reducing sugars was used to construct for the first time a panel of linkage-diversified neoglycosides. This panel of digitoxin analogs included potent and selective tumor cytotoxins; cytotoxicity was dependent on the structure of the glycosidic linkage. These results validate linkage diversification through neoglycosylation as a unique and simple strategy to powerfully complement existing methods for the optimization of glycoconjugates. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.058
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醇 为溶剂， 生成 3β-ethoxyaminodigitoxigenin
  参考文献：
  名称：

  Modifying the glycosidic linkage in digitoxin analogs provides selective cytotoxins

  摘要：

  A chemoselective reaction between oxyamines and unprotected, unactivated reducing sugars was used to construct for the first time a panel of linkage-diversified neoglycosides. This panel of digitoxin analogs included potent and selective tumor cytotoxins; cytotoxicity was dependent on the structure of the glycosidic linkage. These results validate linkage diversification through neoglycosylation as a unique and simple strategy to powerfully complement existing methods for the optimization of glycoconjugates. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.058

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.