2,2-Dimethyl-3-oxo-3-[2-(tetradecanoylamino)ethylamino]propanoic acid | 1445768-43-3

• 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: 2,2-Dimethyl-3-oxo-3-[2-(tetradecanoylamino)ethylamino]propanoic acid
• 英文别名: 2,2-dimethyl-3-oxo-3-[2-(tetradecanoylamino)ethylamino]propanoic acid
• CAS: 1445768-43-3
• 化学式: C₂₁H₄₀N₂O₄
• 分子量: 384.56
• InChiKey: IAWSZIDTEALBQU-UHFFFAOYSA-N

物化性质

• 沸点：
  615.2±40.0 °C(predicted)
• 密度：
  1.007±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-3-oxo-3-[2-(tetradecanoylamino)ethylamino]propanoic acid 、 2'-aminoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 (2R,3R,4S,5S,6S)-2-(acetoxymethyl)-6-(2-(2,2-dimethyl-3-oxo-3-((2-tetradecanamidoethyl)amino)propanamido)ethoxy)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
• 作为产物：
  描述：

  2,2-二甲基丙二酸单甲酯 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.17h， 生成 2,2-Dimethyl-3-oxo-3-[2-(tetradecanoylamino)ethylamino]propanoic acid
  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.