N,N-dihexadecyl-6-methoxybenzothiazol-2-amine | 1577230-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N,N-dihexadecyl-6-methoxybenzothiazol-2-amine
• CAS: 1577230-72-8
• 化学式: C₄₀H₇₂N₂OS
• 分子量: 629.09
• InChiKey: PJCPTUBDSIZFBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.07
• 重原子数：
  44.0
• 可旋转键数：
  32.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  25.36
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N,N-dihexadecyl-6-methoxybenzothiazol-2-amine 在 吡啶盐酸盐 作用下， 以 甲醇 、 melt 、 氯仿 为溶剂， 反应 15.0h， 生成 N,N-dihexadecyl-6-hydroxy-N-methylbenzothiazol-2-ammonium chloride
  参考文献：
  名称：

  Benzothiazole head group based cationic lipids: Synthesis and application for gene delivery

  摘要：

  A series of benzothiazole based lipids (1-10) containing different derivatives of benzothiazole in the head group region were synthesized to determine the structure activity relationship for gene delivery. The liposomes formulated were mixed with plasmid DNA encoding green fluorescent protein (alpha 5GFP) or beta-galactosidase (pCMV-SPORT-beta-gal) and transfected into B16F10 (Human melanoma cancer cells), CHO (Chinese hamster ovary), A-549 (Human lung carcinoma cells) and MCF-7 (Human breast carcinoma cells) types of cell lines. The efficiencies of lipids 9 and 10 in particular, were found to be comparable and even more when compared to that of LipofectAmine-2000. The transfection profiles of the efficient lipids are proved to be maintained even in the presence of serum. Thus, the benzothiazole head group based lipids developed have the potential to be used as transfection reagents in vitro and in vivo. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.034
• 作为产物：
  描述：

  2-氨基-6-甲氧基苯并噻唑 、 溴代十六烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以54%的产率得到N,N-dihexadecyl-6-methoxybenzothiazol-2-amine
  参考文献：
  名称：

  Benzothiazole head group based cationic lipids: Synthesis and application for gene delivery

  摘要：

  A series of benzothiazole based lipids (1-10) containing different derivatives of benzothiazole in the head group region were synthesized to determine the structure activity relationship for gene delivery. The liposomes formulated were mixed with plasmid DNA encoding green fluorescent protein (alpha 5GFP) or beta-galactosidase (pCMV-SPORT-beta-gal) and transfected into B16F10 (Human melanoma cancer cells), CHO (Chinese hamster ovary), A-549 (Human lung carcinoma cells) and MCF-7 (Human breast carcinoma cells) types of cell lines. The efficiencies of lipids 9 and 10 in particular, were found to be comparable and even more when compared to that of LipofectAmine-2000. The transfection profiles of the efficient lipids are proved to be maintained even in the presence of serum. Thus, the benzothiazole head group based lipids developed have the potential to be used as transfection reagents in vitro and in vivo. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.034