N-(4-bromophenyl)-4-pyridinecarboxamide | 14547-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-bromophenyl)-4-pyridinecarboxamide
• 英文别名: Isonicotinsaeure-4-brom-anilid；Isonicotinamide, N-(4-bromophenyl)-；N-(4-bromophenyl)pyridine-4-carboxamide
• CAS: 14547-70-7
• 化学式: C₁₂H₉BrN₂O
• mdl: MFCD00777904
• 分子量: 277.12
• InChiKey: GGRSQPUETTVASD-UHFFFAOYSA-N

物化性质

• 熔点：
  214 °C(Solv: ethanol (64-17-5))
• 沸点：
  311.4±22.0 °C(Predicted)
• 密度：
  1.559±0.06 g/cm3(Predicted)
• 保留指数：
  2278

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-(4-bromophenyl)-4-pyridinecarboxamide 、 1,10-二溴癸烷 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到1,1'-(1,10-decanediyl)bis[4-[[4-(bromo)phenylamino]carbonyl]pyridinium bromide]
  参考文献：
  名称：

  Pyridinium cationic-dimer antimalarials, unlike chloroquine, act selectively between the schizont stage and the ring stage of Plasmodium falciparum

  摘要：

  Malaria is a leading cause of death in developing countries, and the emergence of strains resistant to the main therapeutic agent, chloroquine, has become a serious problem. We have developed cationic-dimer type antimalarials, MAP-610 and PMAP-H10, which are structurally different from chloroquine. In this study, we introduced several substituents on the terminal phenyl rings of PMAP-H10. The electronic and hydrophobic properties of the substituents were correlated with the antimalarial activity and cytotoxicity of the compounds, respectively. Studies with synchronized cultures of malarial plasmodia showed that our cationic-dimers act selectively between the schizont stage and the ring stage of the parasitic cycle, unlike chloroquine, which has a stage-independent action. Thus, the mechanism of action of our antimalarials appears to be different from that of chloroquine, and our compounds may be effective against chloroquine-resistant strains. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.04.051
• 作为产物：
  描述：

  异烟酸 、 4-溴苯胺 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以65%的产率得到N-(4-bromophenyl)-4-pyridinecarboxamide
  参考文献：
  名称：

  Pyridinium cationic-dimer antimalarials, unlike chloroquine, act selectively between the schizont stage and the ring stage of Plasmodium falciparum

  摘要：

  Malaria is a leading cause of death in developing countries, and the emergence of strains resistant to the main therapeutic agent, chloroquine, has become a serious problem. We have developed cationic-dimer type antimalarials, MAP-610 and PMAP-H10, which are structurally different from chloroquine. In this study, we introduced several substituents on the terminal phenyl rings of PMAP-H10. The electronic and hydrophobic properties of the substituents were correlated with the antimalarial activity and cytotoxicity of the compounds, respectively. Studies with synchronized cultures of malarial plasmodia showed that our cationic-dimers act selectively between the schizont stage and the ring stage of the parasitic cycle, unlike chloroquine, which has a stage-independent action. Thus, the mechanism of action of our antimalarials appears to be different from that of chloroquine, and our compounds may be effective against chloroquine-resistant strains. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.04.051

文献信息

• Rhodium(iii)-catalyzed oxidative mono- and di-olefination of isonicotinamides
  作者：Xiaohong Wei、Feng Wang、Guoyong Song、Zhengyin Du、Xingwei Li

  DOI：10.1039/c2ob25773d

  日期：——

  [RhCp*Cl2]2 can catalyze the oxidative coupling of secondary isonicotinamides with activated olefins using Cu(OAc)2 as an oxidant. The selectivity can be controlled by the solvent. In MeCN, the mono-olefination and two-fold oxidation reaction is the major pathway, while in THF this reaction gave mostly diolefination products. In both cases, the coupled products contain an exocyclic CC bond.

  [RhCp*Cl2]2能催化次异烟酰胺与活泼烯烃的氧化偶联反应，以Cu(OAc)2作为氧化剂。通过溶剂可以选择性地控制反应。在乙腈中，单烯化与双氧化反应是主要途径，而在四氢呋喃中该反应主要得到二烯化产物。两种情况下，偶联产物都含有一个环外碳碳键。
• Sulfur–DMSO promoted oxidative coupling of active methylhetarenes with amines: access to amides
  作者：Thi Thu Tram Nguyen、Viet Dung Duong、Thi Ngoc Nga Pham、Quoc Thanh Duong、Thanh Binh Nguyen

  DOI：10.1039/d2ob01709a

  日期：——

  The elemental sulfur–DMSO couple was found to efficiently promote the oxidative coupling of active methylhetarenes with amines to yield amides under simple heating conditions. When 2-methylquinoline was used as the methylhetarene component, the formation of the expected 2-quinolinecarboxamides from anilines could be efficiently catalyzed by iron, nickel and cobalt salts. The method displayed good functional

  发现元素硫-DMSO 对在简单的加热条件下有效地促进活性甲基杂芳烃与胺的氧化偶联生成酰胺。当使用 2-甲基喹啉作为甲基杂芳烃组分时，铁盐、镍盐和钴盐可以有效地催化苯胺生成预期的 2-喹啉甲酰胺。该方法表现出良好的官能团耐受性，适用于芳香胺、杂芳香胺和脂肪胺。其他底物，如苯乙酸、二苄基二硫化物和苄胺，可以代替甲基杂环烯作为有效的伙伴。
• LETTAU, H.;MUELLER, J.;BERGMANN, I.;SCHUBERT, H.;SEEWALD, I.;WEISER, H.
  作者：LETTAU, H.、MUELLER, J.、BERGMANN, I.、SCHUBERT, H.、SEEWALD, I.、WEISER, H.

  DOI：——

  日期：——