N-(pyridine-2-carboxaldehyde)benzhydrazone | 5475-70-7

• 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-(pyridine-2-carboxaldehyde)benzhydrazone
• 英文别名: 2-pyridylcarboxaldehyde benzoyl hydrazone；N-(pyridin-2-ylmethylideneamino)benzamide
• CAS: 5475-70-7
• 化学式: C₁₃H₁₁N₃O
• mdl: MFCD00434535
• 分子量: 225.25
• InChiKey: FEHWEDNVSQUYNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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

反应信息

• 作为反应物：
  描述：

  N-(pyridine-2-carboxaldehyde)benzhydrazone 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  羧酰亚胺铁(II)配合物的制备与表征

  摘要：

  摘要 C5H4NCH NNHC(O)Ph (1) 与氯化 Fe(II) 反应得到 [Fe2(C5H4NC(OEt) NNHC(O)Ph)2(μ-OEt)2Cl2]) (2) 在乙醇和 [Fe2 (C5H4NC(OMe) NNHC(O)Ph)2(μ-OMe)2Cl2] (3) 在甲醇中以及 [Fe(C5H4NCH NNHC(O)Ph)Cl2] (4) 在四氢呋喃中。X 射线衍射分析揭示了它们的结构，配合物 4 被认为是形成配合物 2 和 3 的中间体。

  DOI：

  10.1016/j.inoche.2004.10.019
• 作为产物：
  描述：

  苯甲酸 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N-(pyridine-2-carboxaldehyde)benzhydrazone
  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

• Rapid and reversible hydrazone bioconjugation in cells without the use of extraneous catalysts
  作者：Rahul Nisal、Gregor P. Jose、Chitra Shanbhag、Jeet Kalia

  DOI：10.1039/c8ob00946e

  日期：——

  typically performed in the presence of a large excess of cytotoxic aniline-based nucleophilic catalysts, rendering hydrazones unsuitable for biological applications that entail their formation in cells. Herein, we report a hydrazine scaffold—o-amino benzyl hydrazine—that rapidly forms hydrazones via intramolecular nucleophilic catalysis, thereby obviating the use of extraneous catalysts. We demonstrate

  of键易于通过在弱酸性水溶液中水解或在胺类亲核试剂处理后进行氨基转移而分解的能力，使其在化学生物学，药物递送和材料科学中的应用极具吸引力。但是，不幸的是，from的使用因其肼和羰基前体形成的固有速率极慢而受到阻碍。因此，的形成通常在大量过量的基于细胞毒性苯胺的亲核催化剂存在下进行，从而使不适合需要在细胞中形成的生物应用。在此，我们报道了一种肼基骨架-邻氨基苄基肼-可通过以下方式快速形成分子内亲核催化，从而避免了使用外来催化剂。我们证明了这种支架用于快速和可逆的肽和蛋白质生物共轭作用，也可用于哺乳动物细胞中唾液酸化糖蛋白和胆碱脂类的可逆荧光标记。
• Hydrazone–diacetyl platinum(II) complexes: Substituent effect on intramolecular N–H⋯O hydrogen-bond strength
  作者：Tim Kluge、Eileen Bette、Martin Bette、Jürgen Schmidt、Dirk Steinborn

  DOI：10.1016/j.jorganchem.2014.03.030

  日期：2014.7

  to yield diacetyl platinum(II) complexes [Pt(COMe)2(2-pyCRNNH2)] (R = H, 4a; Me, 4b; Ph, 4c) and [Pt(COMe)2(H2NNCMe–CMeNNH2)] (5). These complexes showed weak intramolecular N–H⋯O hydrogen bonds where the hydrazone and the acetyl ligand act as H donor and H acceptor, respectively. Using hydrazones 2-pyCRNNHR′ substituted with electron-withdrawing groups R′ resulted in complexes [Pt(COMe)2(2-pyCRNNHR′)]

  双（苄胺）二乙酰铂（II）（3）与2-吡啶基官能化的和二乙酰二hydr反应生成二乙酰铂（II）配合物[Pt（COMe）2（2-pyCR NNH 2）]（R = H，4a ; Me，4b ; Ph，4c）和[Pt（COMe）2（H 2 NN CMe–CMe NNH 2）]（5）。这些配合物显示出较弱的分子内N–H⋯O氢键，其中and和乙酰基配体分别充当H供体和H受体。使用被吸电子基团R'取代的2- 2-pyCR NNHR'生成配合物[Pt（COMe）2（2- pyCR NNHR'）]（R / R'= H / C 6 H ^ 4 - p -F，6D ;我/ C 6 H ^ 4 - p -F，6E ; H /来，图7a ; ME /来，7b ; H / COPh，7c ; Me / COPh，7d ; H / CO（C 6 H 4 - p -F），7e ; Me / CO（C 6 H 4 - p
• Indoline Catalyzed Acylhydrazone/Oxime Condensation under Neutral Aqueous Conditions
  作者：Yuntao Zhou、Irene Piergentili、Jennifer Hong、Michelle P. van der Helm、Mariano Macchione、Yao Li、Rienk Eelkema、Sanzhong Luo

  DOI：10.1021/acs.orglett.0c02128

  日期：2020.8.7

  condensation rate under neutral conditions limits its application. Herein, indolines with electron-donating groups are reported as a new catalyst scaffold, which can catalyze acylhydrazone, hydrazone, and oxime formation via an iminium ion intermediate. This new type of catalyst showed up to 15-fold rate enhancement over the traditional aniline-catalyzed reaction at neutral conditions. The identified

  酰基hydr的形成已广泛应用于材料科学和生物标记中。然而，它们在中性条件下的凝结速率缓慢，限制了其应用。在本文中，具有电子给体基团的二氢吲哚被报道为新的催化剂支架，其可以通过亚胺离子中间体催化酰基hydr，和肟的形成。在中性条件下，这种新型催化剂显示出比传统苯胺催化反应高出15倍的速率增强。鉴定出的二氢吲哚催化剂已成功应用于水凝胶的形成。
• I₂-Mediated Oxidative C–O Bond Formation for the Synthesis of 1,3,4-Oxadiazoles from Aldehydes and Hydrazides
  作者：Wenquan Yu、Gang Huang、Yueteng Zhang、Hongxu Liu、Lihong Dong、Xuejun Yu、Yujiang Li、Junbiao Chang

  DOI：10.1021/jo401751h

  日期：2013.10.18

  A practical and transition-metal-free oxidative cyclization of acylhydrazones into 1,3,4-oxadiazoles has been developed by employing stoichiometric molecular iodine in the presence of potassium carbonate. The conditions of this cyclization reaction also work well with crude acylhydrazone substrates obtained from the condensation of aldehydes and hydrazides. A series of symmetrical and asymmetrical

  通过在碳酸钾存在下使用化学计量的分子碘，已开发出一种实用且无过渡金属的酰基hydr酮成1,3,4-恶二唑的氧化环化反应。该环化反应的条件也适用于由醛和酰肼的缩合得到的粗酰基hydr底物。可以以有效和可扩展的方式方便地生成一系列对称和不对称的2,5-二取代的（芳基，烷基和/或乙烯基）1,3,4-恶二唑。
• Pseudohalide-induced structural variations in hydrazone-based metal complexes: Syntheses, electrochemical studies and structural aspects
  作者：Sambuddha Banerjee、Aurkie Ray、Soma Sen、Samiran Mitra、David L. Hughes、Ray J. Butcher、Stuart R. Batten、David R. Turner

  DOI：10.1016/j.ica.2008.01.019

  日期：2008.6

  The effects of pseudohalides on the modes of binding of a hydrazone ligand are investigated and we report here four new hydrazone complexes [Co(L) 2 ] · ClO 4 ( 1 ), [Co(L) 2 ] 2 [Co(SCN) 4 ] ( 2 ), [Mn(L) 2 ] ( 3 ) and [Mn(N 3 ) 2 ( LH ) 2 ] · H 2 O ( 4 ) [where LH = condensation product of pyridine-2-carboxaldehyde and benzhydrazide]. The hydrazone ligand is quite diverse in its chelating ability

  假卤化物对a配体的结合模式的影响进行了调查，我们在这里报告了四个新的complex配合物[Co（L）2]·ClO 4（1），[Co（L）2] 2 [Co（SCN） 4]（2），[Mn（L）2]（3）和[Mn（N 3）2（LH）2]·H 2 O（4）[其中LH =吡啶-2-羧醛与苯甲酰肼的缩合产物]。配体的螯合能力非常不同，可以用作中性或单负性配体，也可以用作二齿或三齿单元。在本文中，我们报告了结构，这些结构显示了具有不同电荷的配体的不同密度。通过IR，UV-Vis光谱学和循环伏安法研究对复合物进行表征，并通过单晶X射线衍射研究最终确定了结构。在综合体中