(E)-4-nitro-N'-(pyridine-2-ylmethylene)benzohydrazide

• 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: (E)-4-nitro-N'-(pyridine-2-ylmethylene)benzohydrazide
• 英文别名: (E)-4-nitro-N'-(pyridin-2-ylmethylene)benzohydrazide；(E)-4-nitro-N'-(pyridin-2-ylmethylene)benzhydrazide；4-nitro-benzoic acid-([2]pyridylmethylene-hydrazide)；4-Nitro-benzoesaeure-([2]pyridylmethylen-hydrazid)；4-nitro-N-[(E)-pyridin-2-ylmethylideneamino]benzamide
• 化学式: C₁₃H₁₀N₄O₃
• 分子量: 270.247
• InChiKey: SSGCHTFAHFBUJG-OQLLNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 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：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-4-nitro-N'-(pyridine-2-ylmethylene)benzohydrazide 以 氘代甲醇 为溶剂， 生成 (Z)-4-nitro-N'-(pyridin-2-ylmethylene)benzhydrazide
  参考文献：
  名称：

  构造和构造信息存储：基于吡啶基和酰基Hy的系统中的多种动力学

  摘要：

  的CN基团可以经历E / Z通过光化学和热异构化，可以生成一个封闭的过程，该过程可以通过这两个物理刺激中的任何一个进行调整。另一方面，肼交换反应可以使给定的发生结构变化。这两类过程：1）构造（物理刺激）和2）构造（化学刺激）分别允许访问短期和长期信息存储。本文报道了两个（双吡啶yl和2-吡啶羧甲醛苯hydr）经历了封闭，化学或物理驱动的过程，并且可以通过金属离子配位或去除随意锁定或解锁，从而实现了这种转化。这些特征还扩展到源自2-吡啶甲醛的酰基。类似于类吡啶的 此类酰基可同时发生结构和构型变化，以及金属离子配位变化。所有这些类型的均代表能够充当多态分子装置的动力学系统，其中配位位点的存在还允许金属离子控制的锁定和解锁不同状态之间的相互转化。

  DOI：

  10.1002/chem.201002308
• 作为产物：
  描述：

  (Z)-4-nitro-N'-(pyridin-2-ylmethylene)benzhydrazide 生成 (E)-4-nitro-N'-(pyridine-2-ylmethylene)benzohydrazide
  参考文献：
  名称：

  构造和构造信息存储：基于吡啶基和酰基Hy的系统中的多种动力学

  摘要：

  的CN基团可以经历E / Z通过光化学和热异构化，可以生成一个封闭的过程，该过程可以通过这两个物理刺激中的任何一个进行调整。另一方面，肼交换反应可以使给定的发生结构变化。这两类过程：1）构造（物理刺激）和2）构造（化学刺激）分别允许访问短期和长期信息存储。本文报道了两个（双吡啶yl和2-吡啶羧甲醛苯hydr）经历了封闭，化学或物理驱动的过程，并且可以通过金属离子配位或去除随意锁定或解锁，从而实现了这种转化。这些特征还扩展到源自2-吡啶甲醛的酰基。类似于类吡啶的 此类酰基可同时发生结构和构型变化，以及金属离子配位变化。所有这些类型的均代表能够充当多态分子装置的动力学系统，其中配位位点的存在还允许金属离子控制的锁定和解锁不同状态之间的相互转化。

  DOI：

  10.1002/chem.201002308

文献信息

• Configurational and Constitutional Information Storage: Multiple Dynamics in Systems Based on Pyridyl and Acyl Hydrazones
  作者：Manuel N. Chaur、Daniel Collado、Jean-Marie Lehn

  DOI：10.1002/chem.201002308

  日期：2011.1.3

  acyl hydrazones can undergo both constitutional and configurational changes, as well as metal‐ion coordination. All these types of hydrazones represent dynamic systems capable of acting as multiple state molecular devices, in which the presence of coordination sites furthermore allows the metal ion‐controlled locking and unlocking of the interconversion of the different states.

  的CN基团可以经历E / Z通过光化学和热异构化，可以生成一个封闭的过程，该过程可以通过这两个物理刺激中的任何一个进行调整。另一方面，肼交换反应可以使给定的发生结构变化。这两类过程：1）构造（物理刺激）和2）构造（化学刺激）分别允许访问短期和长期信息存储。本文报道了两个（双吡啶yl和2-吡啶羧甲醛苯hydr）经历了封闭，化学或物理驱动的过程，并且可以通过金属离子配位或去除随意锁定或解锁，从而实现了这种转化。这些特征还扩展到源自2-吡啶甲醛的酰基。类似于类吡啶的 此类酰基可同时发生结构和构型变化，以及金属离子配位变化。所有这些类型的均代表能够充当多态分子装置的动力学系统，其中配位位点的存在还允许金属离子控制的锁定和解锁不同状态之间的相互转化。
• 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.
• Grammaticakis, Bulletin de la Societe Chimique de France, 1956, p. 109,115
  作者：Grammaticakis

  DOI：——

  日期：——
• Structure–Activity Relationships of Novel Iron Chelators for the Treatment of Iron Overload Disease: The Methyl Pyrazinylketone Isonicotinoyl Hydrazone Series
  作者：Danuta S. Kalinowski、Philip C. Sharpe、Paul V. Bernhardt、Des R. Richardson

  DOI：10.1021/jm7012562

  日期：2008.1.1

  The design of novel Fe chelators with high Fe mobilization efficacy and low toxicity remains an important priority for the treatment of Fe overload disease. We have designed and synthesized the novel methyl pyrazinylketone isonicotinoyl hydrazone (HMPIH) analogs based on previously investigated aroylhydrazone chelators. The HMPIH series demonstrated high Fe mobilization efficacy from cells and showed limited to moderate antiproliferative activity. Importantly, this novel series demonstrated irreversible electrochemistry, which was attributed to the electron-withdrawing effects of the noncoordinating pyrazine N-atom. The latter functionality played a major role in forming redox-inactive complexes that prevent reactive oxygen species generation. In fact, the Fe complexes of the HMPIH series prevented the oxidation of ascorbate and hydroxylation of benzoate. We determined that the incorporation of electron-withdrawing groups is an important feature in the design of N,N,O-aroylhydrazones as candidate drugs for the treatment of Fe overload disease.
• Some trans-chlorobis(triphenylphosphine)ruthenium(II) complexes with N,N,O-donor N-(aroyl)-N′-(picolinylidene)hydrazines
  作者：Raji Raveendran、Samudranil Pal

  DOI：10.1016/j.poly.2004.09.027

  日期：2005.1

  The reactions of [Ru(PPh3)(3)Cl-2] and N-(aroyl)-N'-(picolinylidene)hydrazines (HL): derived from 2-pyridinecarbaldehyde and 4-substituted aroylhydrazines in boiling methanol provide mixed-ligand complexes having the general formula trans-[RuL(PPh3)(2)Cl]. The complexes were characterized by analytical, spectroscopic and electrochemical measurements. The +2 oxidation state of the metal ions in these complexes is confirmed by their diamagnetic nature in the solid state and electrically non-conducting behavior in solution. The X-ray structure of a representative complex has been determined. The metal ion is in a distorted octahedral N2OP2Cl coordination sphere. The monoanionic pyridine-N. imine-N and deprotonated amide-O donor ligand and the chlorine atom form an N2OCl square-plane around the metal centre and the P-atoms of the PPh3 Molecules OCCUPY the remaining two axial sites. The P-31 NMR spectra of all the complexes in CDCl3 solutions are consistent with the irons orientation of the PPh3 molecules. Electronic spectra of the complexes in dichloromethane solution display several bands in the range 590-261 nm due to metal-to-ligand charge transfer and intraligand transitions. Cyclic voltammograms of the complexes in dimethylformamide solution display the reversible Ru(III)/Ru(II) couple in the potential range 0.40-0.52 V (versus saturated calomel electrode). The trend in these potential values reflects the polar effect of the substituents on the aroyl moiety of the ligand (L-). (C) 2004 Elsevier Ltd. All rights reserved.