N-(pyridin-4-ylmethylideneamino)benzamide | 1507-93-3

• 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-(pyridin-4-ylmethylideneamino)benzamide
• CAS: 1507-93-3
• 化学式: C₁₃H₁₁N₃O
• mdl: MFCD00161048
• 分子量: 225.25
• InChiKey: IDBRDJFOFNLZRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  N-(pyridin-4-ylmethylideneamino)benzamide 在 N-氯代丁二酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine
  参考文献：
  名称：

  N-Chlorosuccinimide/1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) – 2,5-Di 取代 1,3,4-Oxadiazoles 的介导合成

  摘要：

  N-氯代琥珀酰亚胺和1,8-二氮杂双环[5.4.0]十一碳-7-烯的混合物氧化环化结构多样的酰基腙，从而为合成各种2,5-二取代的1,3、 4-恶二唑。该方法的显着特点是反应条件温和、反应时间短、收率高、后处理程序简单。

  DOI：

  10.1080/00397910903134592
• 作为产物：
  描述：

  苯甲酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N-(pyridin-4-ylmethylideneamino)benzamide
  参考文献：
  名称：

  Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs

  摘要：

  Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.040

文献信息

• Indium(I)-Catalyzed Asymmetric Allylation, Crotylation, and α-Chloroallylation of Hydrazones with Rare Constitutional and High Configurational Selectivities
  作者：Ananya Chakrabarti、Hideyuki Konishi、Miyuki Yamaguchi、Uwe Schneider、Shū Kobayashi

  DOI：10.1002/anie.200906308

  日期：2010.3.1

  The hydra‐zone: The first example of asymmetric InI catalysis had been developed. InI combined with a chiral semicorrin ligand (L*) is an effective catalyst for enantioselective allylation, crotylation, and α‐chloroallylation of hydrazones. In the two latter cases, CC bond formations proceeded with high selectivity where both reactive aliphatic CCl and aromatic OH bonds were tolerated.

  区：开发了不对称In I催化的第一个例子。InI与手性半corrin配体（L *）结合是hydr的对映选择性烯丙基化，丁烯酰化和α-氯代烯丙基化的有效催化剂。在后两种情况下，CC键的形成过程具有很高的选择性，同时可以容忍反应性脂族CCl和芳族OH键。
• Convenient preparation of unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess–Martin reagent
  作者：Cristian Dobrotă、Codruţa C. Paraschivescu、Ioana Dumitru、Mihaela Matache、Ion Baciu、Lavinia L. Ruţă

  DOI：10.1016/j.tetlet.2009.02.054

  日期：2009.4

  2,5-Disubstituted 1,3,4-oxadiazoles have been conveniently prepared by oxidative cyclization of N-acyl-N'-aryliden-hydrazines promoted by all excess or Dess-Martin periodinane under Mild conditions (23 examples, up to 92% isolated yields). (C) 2009 Elsevier Ltd. All rights reserved.
• Potent antimicrobial agents against azole-resistant fungi based on pyridinohydrazide and hydrazomethylpyridine structural motifs
  作者：Gregory L. Backes、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmc.2015.04.040

  日期：2015.7

  Schiff base derivatives have recently been shown to possess antimicrobial activity, and these derivatives include a limited number of salicylaldehyde hydrazones. To further explore this structure-activity relationship between salicylaldehyde hydrazones and antifungal activity, we previously synthesized and analyzed a large series of salicylaldehyde and formylpyridinetrione hydrazones for their ability to inhibit fungal growth of both azole-susceptible and azole-resistant species of Candida. While many of these analogs showed excellent growth inhibition with low mammalian cell toxicity, their activity did not extend to azole-resistant species of Candida. To further dissect the structural features necessary to inhibit azole-resistant fungal species, we synthesized a new class of modified salicylaldehyde derivatives and subsequently identified a series of modified pyridine-based hydrazones that had potent fungicidal antifungal activity against multiple Candida spp. Here we would like to present our synthetic procedures as well as the results from fungal growth inhibition assays, mammalian cell toxicity assays, time-kill assays and synergy studies of these novel pyridine-based hydrazones on both azole-susceptible and azole-resistant fungal species. (C) 2015 Elsevier Ltd. All rights reserved.
• N-Chlorosuccinimide/1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)–Mediated Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles
  作者：Santosh P. Pardeshi、Sachin S. Patil、Vivek D. Bobade

  DOI：10.1080/00397910903134592

  日期：2010.5.11

  N-chlorosuccinimide and 1,8-diazabicyclo[5.4.0]undec-7-ene oxidatively cyclizes structurally diverse acyl hydrazone, thereby providing an efficient and convenient method for the synthesis of various 2,5-disubstituted 1,3,4-oxadiazoles. The salient features of this method are mild reaction conditions, short reaction time, excellent yields, and simple workup procedure.

  N-氯代琥珀酰亚胺和1,8-二氮杂双环[5.4.0]十一碳-7-烯的混合物氧化环化结构多样的酰基腙，从而为合成各种2,5-二取代的1,3、 4-恶二唑。该方法的显着特点是反应条件温和、反应时间短、收率高、后处理程序简单。