4,6-dichloro-N-hexadecyl-1,3,5-triazin-2-amine | 1221971-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 4,6-dichloro-N-hexadecyl-1,3,5-triazin-2-amine
• CAS: 1221971-58-9
• 化学式: C₁₉H₃₄Cl₂N₄
• 分子量: 389.412
• InChiKey: NAEIBGSNMMPZPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-N-hexadecyl-1,3,5-triazin-2-amine 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Efficient Cell Transfection with Melamine-Based Gemini Surfactants

  摘要：

  Gemini surfactants consisting of two melamine scaffolds connected by a n-hexyl linker and functionalized with a 1-propylammonium polar head and a lipophilic chain having variable carbon length (from C8 to C16) were synthesized. These were then used successfully for the transfection of A549, U87 MG, and Bristol 8 cell lines with maxGFP expressing plasmid. The transfection protocol was optimized appropriately (confluence, reagent/pcDNA ratio, compaction time, and transfection time) for each cell line. Under optimized conditions, the C12 and C14 melamine gemini surfactants showed little toxicity and remarkable transfection efficiency, superior to the gold-standard Lipofectamine 2000. These reagents were also able to efficiently transfect primary DRG neurons, which are notoriously difficult to transfect. The presence of serum completely inhibited the transfection capacity of these reagents. Owing to their ready availability, straightforward synthesis, high chemical stability (even in solution), ease of use (no formulation is required), improved transfection ability, and low toxicity, melamine-based gemini surfactants are very promising reagents for cellular DNA transfection.

  DOI：

  10.1021/bc3004292
• 作为产物：
  描述：

  三聚氯氰 、 十六胺 反应 1.5h， 生成 4,6-dichloro-N-hexadecyl-1,3,5-triazin-2-amine
  参考文献：
  名称：

  作为抗菌剂的可持续三嗪衍生季铵盐

  摘要：

  报道了高效抗菌三嗪衍生双咪唑季铵盐 (TQAS) 的第一个例子。 TQAS 采用简单、原子效率高、经济上可持续的策略制备，并作为抗菌剂进行测试，达到 MIC 值低于 10 mg L -1 。独特的是，TQAS 具有低 MIC 和低细胞毒性。

  DOI：

  10.1039/d1ra03455c

文献信息

• A Novel Alkyl Sulphobetaine Gemini Surfactant Based on S-triazine: Synthesis and Properties
  作者：Ruixia Niu、Chao Wang、Zhigang Sun、Biao Long、Hua Song、Weidong Ren、Daqiang Wang、Junyao He

  DOI：10.1007/s11743-017-1996-y

  日期：2017.11

  A series of alkyl sulphobetaine Gemini surfactants Cn‐GSBS (n = 8, 10, 12, 14, 16) was synthesized, using aliphatic amine, cyanuric chloride, ethylenediamine, N,N′‐dimethyl‐1,3‐propyldiamine and sodium 2‐chloroethane sulfonate as main raw materials. The chemical structures were confirmed by FT‐IR, 1H NMR and elemental analysis. The Krafft points differ markedly with different carbon chain length, for

  使用脂肪族胺，氰尿酰氯，乙二胺，N，N′-二甲基-1,3-丙二胺和钠合成了一系列烷基磺基甜菜碱双子表面活性剂C n -GSBS（n = 8、10、12、14、16 ）2-氯乙烷磺酸盐为主要原料。化学结构通过FT-IR，1 H NMR和元素分析确认。不同碳链长度的Krafft点明显不同，对于C 8‐ GSBS，C 10‐ GSBS和C 12‐ GSBS被认为低于0°C，而C 14‐ GSBS，C 16被认为低于0°C‐GSBS高于0°C但低于室温。通过表面张力和电导率研究了表面活性性质。临界胶束浓度远低于十二烷基磺基甜菜碱（BS-12），并且随着碳链长度从8增加到16而降低，对于C 16 -GSBS，其最低浓度可低至5×10 -5 mol L -1。还研究和讨论了碳链长度和C n -GSBS浓度对原油乳液稳定性的影响。
• Sustainable triazine-derived quaternary ammonium salts as antimicrobial agents
  作者：Andrea Morandini、Emanuele Spadati、Benedetta Leonetti、Roberto Sole、Vanessa Gatto、Flavio Rizzolio、Valentina Beghetto

  DOI：10.1039/d1ra03455c

  日期：——

  The first examples of highly efficient antimicrobial triazine-derived bis imidazolium quaternary ammonium salts (TQAS) are reported. TQAS have been prepared with an easy, atom efficient, economically sustainable strategy and tested as antimicrobial agents, reaching MIC values below 10 mg L−1. Distinctively, TQAS have low MIC and low cytotoxicity.

  报道了高效抗菌三嗪衍生双咪唑季铵盐 (TQAS) 的第一个例子。 TQAS 采用简单、原子效率高、经济上可持续的策略制备，并作为抗菌剂进行测试，达到 MIC 值低于 10 mg L -1 。独特的是，TQAS 具有低 MIC 和低细胞毒性。
• Efficient Cell Transfection with Melamine-Based Gemini Surfactants
  作者：Serena Perrone、Michele Usai、Paolo Lazzari、Steven J. Tucker、Heather M. Wallace、Matteo Zanda

  DOI：10.1021/bc3004292

  日期：2013.2.20

  Gemini surfactants consisting of two melamine scaffolds connected by a n-hexyl linker and functionalized with a 1-propylammonium polar head and a lipophilic chain having variable carbon length (from C8 to C16) were synthesized. These were then used successfully for the transfection of A549, U87 MG, and Bristol 8 cell lines with maxGFP expressing plasmid. The transfection protocol was optimized appropriately (confluence, reagent/pcDNA ratio, compaction time, and transfection time) for each cell line. Under optimized conditions, the C12 and C14 melamine gemini surfactants showed little toxicity and remarkable transfection efficiency, superior to the gold-standard Lipofectamine 2000. These reagents were also able to efficiently transfect primary DRG neurons, which are notoriously difficult to transfect. The presence of serum completely inhibited the transfection capacity of these reagents. Owing to their ready availability, straightforward synthesis, high chemical stability (even in solution), ease of use (no formulation is required), improved transfection ability, and low toxicity, melamine-based gemini surfactants are very promising reagents for cellular DNA transfection.