N-(5-chloropyridin-2-yl)butamide | 13606-93-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-chloropyridin-2-yl)butamide
• 英文别名: 2-(N-Butyrylamino)-5-chlor-pyridin；5-chloro-2-aminepyridylbutyramide；N-(5-Chloro-2-pyridyl)butyramide；N-(5-chloropyridin-2-yl)butanamide
• CAS: 13606-93-4
• 化学式: C₉H₁₁ClN₂O
• mdl: MFCD02767272
• 分子量: 198.652
• InChiKey: VNGFAYBNZABZRA-UHFFFAOYSA-N

物化性质

• 沸点：
  370.9±27.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(5-chloropyridin-2-yl)butamide 、 cobalt(II) chloride 以 乙醇 为溶剂， 生成 Co(5-chloro-2-aminepyridybutyramide)2Cl2
  参考文献：
  名称：

  Synthesis, characterization and thermal behavior of cobalt(II) 5-chloro-piridylamides complexes

  摘要：

  Purple cobalt(II) complexes containing 5-chloro-2-aminepyridylacetamide (CPA), 5-chloro-2-aminepyridylpropionamide (CPP) and 5-chloro-2-aminepyridylbutyramide (CPB) ligands were prepared from ethanolic solutions. The general stoichiometry CoL2Cl2 (L = ligand) was determined from elemental analysis data. Infrared results show monodentate CPA and CPP ligands through the aromatic nitrogen atom, CPB is bidentate through the aromatic nitrogen atom and carboxyl group. Thermogravimetric curves under nitrogen showed in the final stage all complexes presented a mixture of cobalt(II) chloride and metallic cobalt as residue. The complexes containing CPA and CPP ligands decomposed in various stages with integral loss of ligand or partial loss of the chloride. Only two steps of decomposition are seen for CPB compound. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0040-6031(03)00285-5
• 作为产物：
  描述：

  2-氨基-5-氯吡啶 、 丁酸 反应 1.5h， 以91%的产率得到N-(5-chloropyridin-2-yl)butamide
  参考文献：
  名称：

  N-Heterocycles Scaffolds as Quorum Sensing Inhibitors. Design, Synthesis, Biological and Docking Studies

  摘要：

  广义上说，群体感知是细菌之间的一种通信系统，用于感知适当的时间来表达它们的毒力因子。群体感知抑制是一种阻断细菌毒力机制的治疗策略。本研究旨在合成和评估新的N-酰基同源半乳糖酮类生物同构体，作为Chromobacterium violaceum CV026中群体感知抑制剂，通过定量测定紫色素的特定产量。合成了五个不同杂环骨架的化合物系列，产率良好：噻唑类化合物16a–c，噻唑啉类17a–c，苯并咪唑类18a–c，吡啶类19a–c和咪唑啉类32a–c。所有15个化合物都显示出作为群体感知抑制剂的活性，除了16a。化合物16b，17a–c，18a，18c，19c和32b在浓度为10 µM和100 µM时表现出活性，突出显示了苯并咪唑18a（IC50 = 36.67 µM）和32b（IC50 = 85.03 µM）的活性。吡啶19c显示出最佳的群体感知抑制活性（IC50 = 9.66 µM）。对所有测试化合物在Chromobacterium violaceum CviR蛋白上进行了分子对接模拟，以深入了解群体感知抑制的过程。计算机辅助数据显示，所有15个化合物与蛋白的亲和力均高于天然的AHL配体（1）。理论结果与实验结果之间存在较强的相关性。

  DOI：

  10.3390/ijms21249512

文献信息

• N-Heterocycles Scaffolds as Quorum Sensing Inhibitors. Design, Synthesis, Biological and Docking Studies
  作者：Alfredo Fuentes-Gutiérrez、Everardo Curiel-Quesada、José Correa-Basurto、Alberto Martínez-Muñoz、Alicia Reyes-Arellano

  DOI：10.3390/ijms21249512

  日期：——

  Quorum sensing is a communication system among bacteria to sense the proper time to express their virulence factors. Quorum sensing inhibition is a therapeutic strategy to block bacterial mechanisms of virulence. The aim of this study was to synthesize and evaluate new bioisosteres of N-acyl homoserine lactones as Quorum sensing inhibitors in Chromobacterium violaceum CV026 by quantifying the specific production of violacein. Five series of compounds with different heterocyclic scaffolds were synthesized in good yields: thiazoles, 16a–c, thiazolines 17a–c, benzimidazoles 18a–c, pyridines 19a–c and imidazolines 32a–c. All 15 compounds showed activity as Quorum sensing inhibitors except 16a. Compounds 16b, 17a–c, 18a, 18c, 19c and 32b exhibited activity at concentrations of 10 µM and 100 µM, highlighting the activity of benzimidazole 18a (IC50 = 36.67 µM) and 32b (IC50 = 85.03 µM). Pyridine 19c displayed the best quorum sensing inhibition activity (IC50 = 9.66 µM). Molecular docking simulations were conducted for all test compounds on the Chromobacterium violaceum CviR protein to gain insight into the process of quorum sensing inhibition. The in-silico data reveal that all 15 the compounds have higher affinity for the protein than the native AHL ligand (1). A strong correlation was found between the theoretical and experimental results.

  广义上说，群体感知是细菌之间的一种通信系统，用于感知适当的时间来表达它们的毒力因子。群体感知抑制是一种阻断细菌毒力机制的治疗策略。本研究旨在合成和评估新的N-酰基同源半乳糖酮类生物同构体，作为Chromobacterium violaceum CV026中群体感知抑制剂，通过定量测定紫色素的特定产量。合成了五个不同杂环骨架的化合物系列，产率良好：噻唑类化合物16a–c，噻唑啉类17a–c，苯并咪唑类18a–c，吡啶类19a–c和咪唑啉类32a–c。所有15个化合物都显示出作为群体感知抑制剂的活性，除了16a。化合物16b，17a–c，18a，18c，19c和32b在浓度为10 µM和100 µM时表现出活性，突出显示了苯并咪唑18a（IC50 = 36.67 µM）和32b（IC50 = 85.03 µM）的活性。吡啶19c显示出最佳的群体感知抑制活性（IC50 = 9.66 µM）。对所有测试化合物在Chromobacterium violaceum CviR蛋白上进行了分子对接模拟，以深入了解群体感知抑制的过程。计算机辅助数据显示，所有15个化合物与蛋白的亲和力均高于天然的AHL配体（1）。理论结果与实验结果之间存在较强的相关性。
• Synthesis, characterization and thermal behavior of cobalt(II) 5-chloro-piridylamides complexes
  作者：C Lima

  DOI：10.1016/s0040-6031(03)00285-5

  日期：2003.12.5

  Purple cobalt(II) complexes containing 5-chloro-2-aminepyridylacetamide (CPA), 5-chloro-2-aminepyridylpropionamide (CPP) and 5-chloro-2-aminepyridylbutyramide (CPB) ligands were prepared from ethanolic solutions. The general stoichiometry CoL2Cl2 (L = ligand) was determined from elemental analysis data. Infrared results show monodentate CPA and CPP ligands through the aromatic nitrogen atom, CPB is bidentate through the aromatic nitrogen atom and carboxyl group. Thermogravimetric curves under nitrogen showed in the final stage all complexes presented a mixture of cobalt(II) chloride and metallic cobalt as residue. The complexes containing CPA and CPP ligands decomposed in various stages with integral loss of ligand or partial loss of the chloride. Only two steps of decomposition are seen for CPB compound. (C) 2003 Elsevier B.V. All rights reserved.