4-chloro-N-(pyrazin-2-yl)benzamide | 91182-98-8

• 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: 4-chloro-N-(pyrazin-2-yl)benzamide
• 英文别名: 2-(4'-chlorobenzoyl)aminopyrazine；4-chloro-N-pyrazin-2-yl-benzamide；4-chloro-N-pyrazin-2-yl-benzamide；p-chlorobenzamidopyrazine；N-Pyrazinyl-4-chlorbenzamide；4-chloro-N-pyrazin-2-ylbenzamide
• CAS: 91182-98-8
• 化学式: C₁₁H₈ClN₃O
• mdl: MFCD00828782
• 分子量: 233.657
• InChiKey: LWTIAYDDQRFEMY-UHFFFAOYSA-N

物化性质

• 溶解度：
  34.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(pyrazin-2-yl)benzamide 在 sodium azide 、 五氯化磷 、 sodium acetate 作用下， 以 水 、 丙酮 为溶剂， 反应 13.0h， 生成 2-[5-(4-Chloro-phenyl)-tetrazol-1-yl]-pyrazine
  参考文献：
  名称：

  Sambaiah, T; Reddy,K Kondal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 7, p. 444 - 445

  摘要：

  DOI：
• 作为产物：
  描述：

  氨基吡嗪 、 4-氯苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以11%的产率得到4-chloro-N-(pyrazin-2-yl)benzamide
  参考文献：
  名称：

  N-吡嗪基苯甲酰胺作为潜在抗分枝杆菌药物的设计、合成和评价

  摘要：

  三个系列的 N-（吡嗪-2-基）苯甲酰胺被设计为先前发表的 N-苯基吡嗪-2-甲酰胺的逆酰胺类似物，具有体外抗分枝杆菌活性。对合成的逆酰胺类化合物对结核分枝杆菌 H37Rv (Mtb)、三种非结核分枝杆菌菌株（鸟分枝杆菌、堪萨斯分枝杆菌、耻垢分枝杆菌）和选定的具有临床重要性的细菌和真菌菌株的体外生长抑制活性进行了评估。关于对 Mtb 的活性，与具有相同取代模式的相应 N-苯基吡嗪-2-甲酰胺相比，大多数 N-吡嗪基苯甲酰胺（逆酰胺）具有较低或没有活性。然而，活性逆酰胺倾向于具有较低的 HepG2 细胞毒性和更好的选择性。与它们的 6-氯位置异构体或非氯化类似物相比，在吡嗪环上具有 5-氯取代的衍生物通常更具活性。在苯环的第 4 位具有短烷基（2h：R2 = Me；2i：R2 = Et）的 N-（5-氯吡嗪-2-基）苯甲酰胺中发现了对 Mtb 的最佳抗分枝杆菌活性（MIC = 6.25 和 3

  DOI：

  10.3390/molecules23092390

文献信息

• Cyclopentadienyl-Free Rare-Earth Metal Amides [{(CH₂SiMe₂){(2,6-<i>i</i>Pr₂C₆H₃)N}₂}Ln{N(SiMe₃)₂}(THF)] as Highly Efficient Versatile Catalysts for C–C and C–N Bond Formation
  作者：Yunjun Wu、Shaowu Wang、Lijun Zhang、Gaosheng Yang、Xiancui Zhu、Zhihong Zhou、Hong Zhu、Shihong Wu

  DOI：10.1002/ejoc.200901015

  日期：2010.1

  Efficient methods have been developed for the direct synthesis of amides from aldehydes and a straightforward route to propiolamidines using cyclopentadienyl-free rare-earth metal amides [(CH 2 SiMe 2 )(2,6-iPr 2 C 6 H 3 )N} 2 }LnN(SiMe 3 ) 2 }-(THF)] [Ln = Yb (1), Y (2), Dy (3), Sm (4), Nd (5)] as versatile catalysts. The results indicate that in the direct synthesis of amides from aldehydes the

  已经开发出从醛直接合成酰胺的有效方法和使用不含环戊二烯基的稀土金属酰胺 [(CH 2 SiMe 2 )(2,6-iPr 2 C 6 H 3 )N } 2 }LnN(SiMe 3 ) 2 }-(THF)] [Ln = Yb (1), Y (2), Dy (3), Sm (4), Nd (5)] 作为通用催化剂。结果表明，在醛直接合成酰胺中，催化剂的活性顺序为2>1∼3∼4∼5。这些方法具有催化剂制备容易、催化剂载量低、底物转化产物转化率高、反应条件温和以及与多种底物相容等优点。
• Diimidazopyrazines and tetracarboxamidopyrazines
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US03959277A1

  公开（公告）日：1976-05-25

  Diimidazopyrazines of the formula: ##SPC1## Wherein R.sup.1 and R.sup.2 are selected from the group consisting of lower alkyl and aryl of 6 to 12 carbons which may be optionally substituted are described. These compounds are useful as brightening agents. They are prepared from tetracarboxamidopyrazines of the formula: ##SPC2## Wherein the R's are as specified above for R.sup.1 and R.sup.2.

  化合物的名称为Diimidazopyrazines，分子式为：##SPC1## 其中R.sup.1和R.sup.2选自以下组合：低碳基和6至12碳的芳基，可以是可选择置换的。这些化合物可用作增白剂。它们是从分子式为：##SPC2## 的四羧酰胺吡嗪中制备而来，其中R的取值与R.sup.1和R.sup.2的取值相同。
• Electrochemistry of Aminoazines and Nitrones: Electrochemical Reductions of 2-Amino-1,4-pyrazine with Nitrones to Form Amide Compounds and Electrochemical Oxidations of Anilines with Nitrones to Form Imine Compounds and Benzaldehydes
  作者：Katsuhiro Saito、Ayako Kawamura、Takashi Kanie、Yosuke Ueda、Satoru Kondo

  DOI：10.3987/com-01-9191

  日期：——

  Electrochemical reductions of 2-amino-1,4-pyrazine in the presence of nitrone derivatives afforded two types of amide compounds, one of which was derived from both the pyrazine and the nitrones and the other from only the nitrones. The analogous reactions but using 2-aminopyridine or aniline instead of the pyrazine resulted in the recovery of the starting materials. On the other hand, electrochemical oxidations of the aminoazine derivatives in the presence of nitrones did not afford any isolatable products. However the reaction using aniline derivatives formed imine compounds accompanied by benzaldehyde derivatives.
• Research on heterocyclic compounds. XXXI. Synthesis and antiinflammatory activity of 2-arylimidazo[1,2-a]pyrazine-3-carboxylic acids
  作者：E Abignente、P de Caprariis、MG Rimoli、L Avallone、L Gomez Paloma、F Rossi、M D'Amico、V Calderaro、C Parrillo

  DOI：10.1016/0223-5234(93)90150-d

  日期：1993.1

  The synthesis of a series of 2-phenyl- and 2-(p-chlorophenyl)imidazo[1,2-a]pyrazine-3-carboxylic esters and acids is described. The structures of the new compounds were supported by H-1- and C-13-NMR spectra. These compounds were evaluated in vivo for their antiinflammatory and analgesic activities as well as for their ulcerogenic potential. Acids 8c and 8e were found to be the most potent antiinflammatory agents (almost-equal-to 1/8 x indomethacin), while 8a, 8d and 8f displayed analgesic activity (almost-equal-to 1/16 x indomethacin). The inhibitory activity on cyclooxygenase action was evaluated in vitro and discussed in comparison with results obtained in vivo.