6-amino-2-dodecanoylaminopyridine | 160413-48-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-amino-2-dodecanoylaminopyridine
• 英文别名: 2-amino-6-lauroylaminopyridine；N-(6-aminopyridin-2-yl)dodecanamide
• CAS: 160413-48-9
• 化学式: C₁₇H₂₉N₃O
• 分子量: 291.437
• InChiKey: WJCCTERAGQHSLN-UHFFFAOYSA-N

物化性质

• 熔点：
  67.5-68.5 °C(Solv: heptane (142-82-5))
• 沸点：
  490.4±30.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-amino-2-dodecanoylaminopyridine 在 sodium azide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 48.0h， 生成 N-[6-[(2-叠氮乙酰基)氨基]吡啶-2-基]十二烷酰胺
  参考文献：
  名称：

  Self-Assembly and Characterization of Supramolecular [60]Fullerene-Containing 2,6-Diacylamidopyridine with Uracil Derivative by Hydrogen-Bonding Interaction

  摘要：

  [GRAPHICS]Novel self-assembly systems of uracil derivatives with organofullerene by a three-point hydrogen-bonding interaction were designed and established. The formation of hydrogen bonding was established by H-1 NMR studies in CDCl3.

  DOI：

  10.1021/ol025614i
• 作为产物：
  描述：

  月桂酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 6-amino-2-dodecanoylaminopyridine
  参考文献：
  名称：

  Self-Assembly and Characterization of Supramolecular [60]Fullerene-Containing 2,6-Diacylamidopyridine with Uracil Derivative by Hydrogen-Bonding Interaction

  摘要：

  [GRAPHICS]Novel self-assembly systems of uracil derivatives with organofullerene by a three-point hydrogen-bonding interaction were designed and established. The formation of hydrogen bonding was established by H-1 NMR studies in CDCl3.

  DOI：

  10.1021/ol025614i

文献信息

• Synthesis and cellular uptake of cell delivering 2,6-pyridinediylbisalkanamide submicron-sized sheets in HeLa cells
  作者：J. S. Yadav、Manoj Kumar Gupta、I. Prathap、Manika Pal Bhadra、Parsi K. Mohan、Bulusu Jagannadh

  DOI：10.1039/b706371g

  日期：——

  2,6-Pyridinediylbisalkanamides were synthesized, using diaminopyridine (DAP) as a linker and alkyl chains of varying lengths, that upon self-assembly form submicron-sized sheets and their uptake into the cytoplasm of HeLa cells was studied by confocal microscopy.

  合成了2,6-吡啶二基双烷酰胺，以二氨基吡啶（DAP）作为连接剂，并使用不同长度的烷基链，经过自组装形成亚微米级的薄片，并通过共聚焦显微镜研究了其在HeLa细胞胞质中的摄取情况。
• DAP derived fatty acid amide organogelators as novel carrier for drug incorporation and pH-responsive release
  作者：Eqvinshi Yadav、Anil Kumar Khatana、Sharol Sebastian、Manoj K. Gupta

  DOI：10.1039/d0nj04611f

  日期：——

  transdermal applications of the NSAIDs with enhanced properties. For this purpose, low molecular mass DAP (2,6-diaminopyridine) derived fatty acid amides with varying alkyl chain lengths are synthesized. These fatty acid amides form stable self-assembled aggregates in organic solvents as well as in organic and aqueous solvent mixtures affording organogels and bigels, respectively. The minimum gelation concentration

  炎症与许多不同类别的疾病有关，长期使用NSAID（非甾体类抗炎药）最为理想。尽管它们可以安全使用，但这类化合物仍会产生一些严重的副作用。因此，局部给药是减少副作用的一种选择。在这项研究中，我们设计了一种新的凝胶制剂，用于具有增强特性的NSAID的局部和透皮应用。为此目的，合成了具有变化的烷基链长的低分子量DAP（2，6-二氨基吡啶）衍生的脂肪酸酰胺。这些脂肪酸酰胺在有机溶剂中以及在有机溶剂和水性溶剂混合物中形成稳定的自组装聚集体，分别提供有机凝胶和双峰。有机凝胶的最小胶凝浓度（MGC）为0.5％w / v，表现得像超级胶凝剂。DAP衍生的脂肪酸酰胺胶凝剂中存在的各种功能在自聚集中起重要作用，例如通过π-π和烷基链的吡啶部分堆叠通过范德华相互作用，形成稳定的有机和Bigels网络。制备的具有这些脂肪酸酰胺的有机凝胶乳液能够在室温下封装和释放药物分子布洛芬，而不会改变其结构和活性。因此，这些类
• N-Long-chain Monoacylated Derivatives of 2,6-Diaminopyridine with Antiviral Activity
  作者：Nobuko Mibu、Kazumi Yokomizo、Nobuhiro Kashige、Fumio Miake、Takeshi Miyata、Masaru Uyeda、Kunihiro Sumoto

  DOI：10.1248/cpb.55.111

  日期：——

  N-Monoacyl-2,6-diaminopyridines (2a—c) and N,N′-diacyl-2,6-diaminopyridines (3a—c) were synthesized from 2,6-diaminopyridine by acylation with the corresponding acyl halide or by dehydration with the corresponding carboxylic acid using 1,3-dicyclohexylcarbodiimide (DCC). The antiviral activities of N-monoacyl- and N,N′-diacyl-2,6-diaminopyridines (2a—c and 3a—c) were estimated using plaque reduction assay with HSV-1. All N-monoacyl derivatives (2a—c) showed significant anti-herpes simplex virus (HSV)-1 activity (EC50=15.3—18.5 μg/ml). The CC50 values of 2a—c measured using Vero cells ranged at 37.5—50.0 μg/ml. These compounds showed no significant antibacterial activities with Escherichia coli or Staphylococcus aureus even at a concentration of 1 mg/ml. The N,N′-diacyl derivatives (3a—c) showed no significant anti-HSV-1 activity.

  N-monoacyl- 2,6-二氨基吡啶（2a-c）和 N,N′-diacyl-2,6-二氨基吡啶（3a-c）是以 2,6-二氨基吡啶为原料，通过与相应的酰基卤进行酰化或使用 1,3-二环己基碳二亚胺（DCC）与相应的羧酸进行脱水而合成的。通过用 HSV-1 进行斑块还原试验，估算了 N-单酰基和 N,N′-二酰基-2,6-二氨基吡啶（2a-c 和 3a-c）的抗病毒活性。所有 N-单酰基衍生物（2a-c）都显示出显著的抗单纯疱疹病毒（HSV）-1 活性（EC50=15.3-18.5 μg/ml）。使用 Vero 细胞测定的 2a-c 的 CC50 值为 37.5-50.0 μg/ml。即使浓度为 1 mg/ml，这些化合物对大肠杆菌或金黄色葡萄球菌也没有明显的抗菌活性。N,N′-二乙酰基衍生物（3a-c）没有显示出明显的抗 HSV-1 活性。
• Tamura, Norio; Mitsui, Keita; Nabeshima, Tatsuya, Journal of the Chemical Society. Perkin transactions II, 1994, # 10, p. 2229 - 2238
  作者：Tamura, Norio、Mitsui, Keita、Nabeshima, Tatsuya、Yano, Yumihiko

  DOI：——

  日期：——
• Self-Assembly and Characterization of Supramolecular [60]Fullerene-Containing 2,6-Diacylamidopyridine with Uracil Derivative by Hydrogen-Bonding Interaction
  作者：Zhiqiang Shi、Yuliang Li、Haofei Gong、Minghua Liu、Shengxiong Xiao、Huibiao Liu、Hongmei Li、Shengqiang Xiao、Daoben Zhu

  DOI：10.1021/ol025614i

  日期：2002.4.1

  [GRAPHICS]Novel self-assembly systems of uracil derivatives with organofullerene by a three-point hydrogen-bonding interaction were designed and established. The formation of hydrogen bonding was established by H-1 NMR studies in CDCl3.