(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(2-(2,2-dimethyl-3-oxo-3-((2-tetradecanamidoethyl)amino)propanamido)ethoxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1445768-47-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(2-(2,2-dimethyl-3-oxo-3-((2-tetradecanamidoethyl)amino)propanamido)ethoxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[2-[[2,2-dimethyl-3-oxo-3-[2-(tetradecanoylamino)ethylamino]propanoyl]amino]ethoxy]-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 1445768-47-7
• 化学式: C₄₉H₇₉N₃O₂₁
• 分子量: 1046.17
• InChiKey: WAIXWFJEJGSWEF-JZLUWYMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  73
• 可旋转键数：
  39
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  308
• 氢给体数：
  3
• 氢受体数：
  21

反应信息

• 作为产物：
  描述：

  β-乳糖 在 吡啶 、 sodium azide 、 palladium on activated charcoal 、 三氟化硼乙醚 、 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.08h， 生成 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(2-(2,2-dimethyl-3-oxo-3-((2-tetradecanamidoethyl)amino)propanamido)ethoxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Glycosylation enhances the anti-migratory activities of isomalyngamide A analogs

  摘要：

  Three, new, fully synthetic glycosylated isomalyngamide A analogs 4-6 were prepared and evaluated for their anti-migratory activities in human breast cancer cells. The results of the study show that two glycosylated derivatives 4 and 5, containing mannose and galactose appendages, suppress metastatic events (e.g., migration, invasion and adhesion) in human breast adenocarcinoma MDA-MB-231 cells at "nontoxic" concentration levels. In contrast, derivative 6 that contains a lactose moiety, displays a less potent activity. The findings show that monosaccharide rather than disaccharide appendages to the isomalyngamide A backbone more greatly influence cell migration and invasive ability. Evidence has been gained for a mechanism for inhibition of metastatic activities in MDA-MB-231 cells by 4 and 5, involving inactivation of the expression of p-FAR and paxillin through the integrin-mediated anti-metastatic pathway. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.044

文献信息

• Glycosylation enhances the anti-migratory activities of isomalyngamide A analogs
  作者：Shivaji V. More、Tzu Ting Chang、Yu-Pin Chiao、Shu-Chuan Jao、Chung-Kuang Lu、Wen-Shan Li

  DOI：10.1016/j.ejmech.2013.03.044

  日期：2013.6

  Three, new, fully synthetic glycosylated isomalyngamide A analogs 4-6 were prepared and evaluated for their anti-migratory activities in human breast cancer cells. The results of the study show that two glycosylated derivatives 4 and 5, containing mannose and galactose appendages, suppress metastatic events (e.g., migration, invasion and adhesion) in human breast adenocarcinoma MDA-MB-231 cells at "nontoxic" concentration levels. In contrast, derivative 6 that contains a lactose moiety, displays a less potent activity. The findings show that monosaccharide rather than disaccharide appendages to the isomalyngamide A backbone more greatly influence cell migration and invasive ability. Evidence has been gained for a mechanism for inhibition of metastatic activities in MDA-MB-231 cells by 4 and 5, involving inactivation of the expression of p-FAR and paxillin through the integrin-mediated anti-metastatic pathway. (C) 2013 Elsevier Masson SAS. All rights reserved.