3-pyridylformaldehyde benzoylhydrazone | 1215-53-8

• 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: 3-pyridylformaldehyde benzoylhydrazone
• 英文别名: N-(pyridin-3-ylmethylideneamino)benzamide
• CAS: 1215-53-8
• 化学式: C₁₃H₁₁N₃O
• mdl: MFCD00033798
• 分子量: 225.25
• InChiKey: JCVMRRDGCPODBY-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：

  3-pyridylformaldehyde benzoylhydrazone 在 碘 、 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以77%的产率得到3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine
  参考文献：
  名称：

  恶二唑的流动合成与连续在线萃取和色谱相结合

  摘要：

  据报道，通过碘介导的氧化环化方法合成各种 1,3,4-恶二唑的有效连续流程。这需要使用填充有固体K 2 CO 3作为基底的加热填充床反应器。该流动方法使用 DMSO 作为溶剂，在 10 分钟的短停留时间内生成目标杂环，收率高达 93%。该流程已实现放大（34 mmol/h），并具有集成的淬灭和萃取步骤。最后，利用自动化在线色谱系统实现了用于生成杂环目标的强大流动平台。

  DOI：

  10.3762/bjoc.18.27
• 作为产物：
  描述：

  苯甲酸乙酯 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 13.5h， 生成 3-pyridylformaldehyde benzoylhydrazone
  参考文献：
  名称：

  一类用于治疗心力衰竭的酰腙类衍生物

  摘要：

  本发明属于医药技术领域，涉及如下通式I所示的一类酰腙类衍生物的设计及制备方法，可用于治疗包括充血性心力衰竭的收缩性心力衰竭。

  公开号：

  CN105481765A

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。
• Development of General Catalytic Allylation of Acylhydrazones with Pinacolyl Allylboronate Using an Indium(I) Catalyst
  作者：Uwe Schneider、I-Hon Chen、Shū Kobayashi

  DOI：10.1021/ol702756k

  日期：2008.3.1

  Catalytic allylation of various acylhydrazones using a group 13 metal reagent (boron) in combination with a group 13 metal catalyst in its low-oxidation state (indium) has been developed. This operationally simple carbon-carbon bond-forming reaction displays remarkable substrate scope and functional group tolerance.

  已经开发了使用第13族金属试剂（硼）与处于低氧化态（铟）的第13族金属催化剂结合的各种酰基hydr的催化烯丙基化反应。这种操作简单的碳-碳键形成反应显示出显着的底物范围和官能团耐受性。
• 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.