tert-butyl N-[2-(tetradecanoylamino)ethyl]carbamate | 1335231-54-3

• 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: tert-butyl N-[2-(tetradecanoylamino)ethyl]carbamate
• CAS: 1335231-54-3
• 化学式: C₂₁H₄₂N₂O₃
• 分子量: 370.576
• InChiKey: SNFRFTAHUWPJFC-UHFFFAOYSA-N

物化性质

• 沸点：
  522.8±33.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-(tetradecanoylamino)ethyl]carbamate 在 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2-(2,2-dimethyl-3-oxo-3-(2-tetradecanamidoethylamino)propanamido)acetic acid
  参考文献：
  名称：

  Isomalyngamide A, A-1 and their analogs suppress cancer cell migration in vitro

  摘要：

  Isomalyngamide A (1) and A-1 (2) were isolated from the Taiwanese Lyngbya majuscule and the latter structure was elucidated by a combination of NMR spectroscopic analysis and HRESIMS measurement. We report the isolation of isomalyngamide A (1), discovery of isomalyngamide A-1 (2) and their synthetic analogs (3-9), which are further demonstrated to have therapeutic potential against tumor cell migration at the level of nanomolar to micromolar ranges, perhaps, by inactivating the expression of p-FAK, FAK, p-Akt and Akt through beta 1 integrin-mediated antimetastatic pathway. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.049
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 生成 tert-butyl N-[2-(tetradecanoylamino)ethyl]carbamate
  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

• Carbon nanodot-induced gelation of a histidine-based amphiphile: application as a fluorescent ink, and modulation of gel stiffness
  作者：Subir Paul、Kousik Gayen、Nibedita Nandi、Arindam Banerjee

  DOI：10.1039/c7cc09824c

  日期：——

  This is a unique example of fluorescent carbon dot-induced hydrogelation of an amino acid-based amphiphile. The carbon dot-to-amphiphile ratio dictates the gel stiffness. Moreover, this hydrogel can be used as a prominent fluorescent ink and the dried gel shows a remarkable, unusual green fluorescence in the solid state.

  这是基于氨基酸的两亲物的荧光碳点诱导的水凝胶化的独特实例。碳点与两亲物的比率决定了凝胶的硬度。此外，该水凝胶可用作显着的荧光墨水，干燥后的凝胶在固态时显示显着的异常绿色荧光。
• Isomalyngamide A, A-1 and their analogs suppress cancer cell migration in vitro
  作者：Tzu Ting Chang、Shivaji V. More、I.-Hsuan Lu、Jui-Ching Hsu、Ting-Ju Chen、Ya Ching Jen、Chung-Kuang Lu、Wen-Shan Li

  DOI：10.1016/j.ejmech.2011.05.049

  日期：2011.9

  Isomalyngamide A (1) and A-1 (2) were isolated from the Taiwanese Lyngbya majuscule and the latter structure was elucidated by a combination of NMR spectroscopic analysis and HRESIMS measurement. We report the isolation of isomalyngamide A (1), discovery of isomalyngamide A-1 (2) and their synthetic analogs (3-9), which are further demonstrated to have therapeutic potential against tumor cell migration at the level of nanomolar to micromolar ranges, perhaps, by inactivating the expression of p-FAK, FAK, p-Akt and Akt through beta 1 integrin-mediated antimetastatic pathway. (C) 2011 Elsevier Masson SAS. All rights reserved.
• 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.