pyridoxal nicotinoyl hydrazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: pyridoxal nicotinoyl hydrazone
• 英文别名: H2pydx-nh；N-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methylideneamino]pyridine-3-carboxamide
• 化学式: C₁₄H₁₄N₄O₃
• mdl: MFCD00763289
• 分子量: 286.29
• InChiKey: TZVNADAFGGITNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 pyridoxal nicotinoyl hydrazone 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  吡ido并的双核铜（II）配合物的合成，磁性和电化学性质

  摘要：

  摘要合成了吡new醛苯甲酰hydr（PBH），吡ido醛邻羟基苯甲酰hydr（PHBH），吡ido吡啶甲基酰yl（PPH），吡ido烟酰yl（PNH）和吡x异烟酰yl（PINH）合成的双核铜（II）配合物。分析，磁性，光谱，ESR和电化学方法。所有复合物在室温下均表现出正常的磁矩。然而，可变温度磁矩表明在配合物中的铜（II）中心之间存在非常弱的分子内反铁磁相互作用（-2J≈〜90 cm-1）。在77 K处的ESR光谱数据是双核CuCu络合物的特征，并且在低场gl区域表现出七线模式。

  DOI：

  10.1016/s0020-1693(00)85517-6
• 作为产物：
  描述：

  nicotinic 在 intestinal mucosa bovine alkaline phosphatase 作用下， 以 aq. buffer 为溶剂， 反应 0.17h， 生成 pyridoxal nicotinoyl hydrazone
  参考文献：
  名称：

  在牛碱性磷酸酶存在下，吡哆醛 5'-磷酸衍生的 Schiff 碱的去磷酸化

  摘要：

  本论文报道了由牛碱性磷酸酶从肠粘膜中诱导的 5'-磷酸吡哆醛和四种衍生腙（含有吡嗪、2-呋喃、2-噻吩、3-吡啶羧酸残基）的去磷酸化作用的研究。 298.2 K 和 pH 10（0.05 m Tris-HCl 缓冲液）。我们观察并讨论了底物的 UV-vis 和荧光光谱的特征变化。计算酶促脱磷酸的 Michaelis-Menten 参数。碱性磷酸酶在腙存在下的稳定性得到证实。分析了 Zn(II) 复合物与吡哆醛 5'-磷酸衍生腙的去磷酸化作用。

  DOI：

  10.1002/kin.21541

文献信息

• Dioxovanadium( <scp>V</scp> ) Complexes of ONO Donor Ligands Derived from Pyridoxal and Hydrazides: Models of Vanadate‐Dependent Haloperoxidases
  作者：Mannar R. Maurya、Shalu Agarwal、Cerstin Bader、Dieter Rehder

  DOI：10.1002/ejic.200400211

  日期：2005.1

  [VO2HL] (H2L = I: 2; H2L = II: 5; H2L = III: 7). Aqueous solutions of vanadate and the ligands at pH = 7.5 give rise to the formation of [K(H2O)3][VO2(pydx-inh)] (3), [K(H2O)2][VO2(pydx-nh)] (6) and [K(H2O)2][VO2(pydx-bhz)] (8). Treatment of 6 and 8 with H2O2 generates the oxo(peroxo)vanadium complexes [VO(O2)L] (H2L = II: 9; H2L = III: 10). Complexes 9 and 10 are capable of transferring an oxo group

  [VO(acac)2] 与 H2L 反应 [H2L 是腙 H2pydx-inh (I)、H2pydx-nh (II) 或 H2pydx-bhz (III)；pydx = 吡哆醛，inh = 异烟酰肼，nh = 烟酰肼，bhz = 苯甲酰肼] 在无水甲醇中生成氧钒 (IV) 配合物 [VOL] (H2L = I: 1; H2L = II: 4) 或 [VO(pydx-bhz) )]。当这些配合物暴露在空气中时，会转化为相应的二氧钒 (V) 配合物 [VO2HL] (H2L = I: 2; H2L = II: 5; H2L = III: 7)。钒酸盐和配体在 pH = 7.5 的水溶液中形成 [K(H2O)3][VO2(pydx-inh)] (3), [K(H2O)2][VO2(pydx-nh) ] (6) 和 [K(H2O)2][VO2(pydx-bhz)] (8)。用 H2O2 处理 6 和
• Novel multifunctional iron chelators of the aroyl nicotinoyl hydrazone class that markedly enhance cellular NAD ⁺ /NADH ratios
  作者：Zhixuan Wu、Duraippandi Palanimuthu、Nady Braidy、Nor Hawani Salikin、Suhelen Egan、Michael L.H. Huang、Des R. Richardson

  DOI：10.1111/bph.14963

  日期：2020.5

  Background and PurposeAlzheimer's disease (AD) is a multifactorial condition leading to cognitive decline and represents a major global health challenge in ageing populations. The lack of effective AD therapeutics led us to develop multifunctional nicotinoyl hydrazones to target several pathological characteristics of AD.Experimental ApproachWe synthesised 20 novel multifunctional agents based on the nicotinoyl hydrazone scaffold, which acts as a metal chelator and a lipophilic delivery vehicle, donating a NAD+ precursor to cells, to target metal dyshomeostasis, oxidative stress, β‐amyloid (Aβ) aggregation, and a decrease in the NAD+/NADH ratio.Key ResultsThe most promising compound, 6‐methoxysalicylaldehyde nicotinoyl hydrazone (SNH6), demonstrated low cytotoxicity, potent iron (Fe)‐chelation efficacy, significant inhibition of copper‐mediated Aβ aggregation, oxidative stress alleviation, effective donation of NAD+ to NAD‐dependent metabolic processes (PARP and sirtuin activity) and enhanced cellular NAD+/NADH ratios, as well as significantly increased median Caenorhabditis elegans lifespan (to 1.46‐fold of the control); partly decreased BACE1 expression, resulting in significantly lower soluble amyloid precursor protein‐β (sAPPβ) and Aβ1–40 levels; and favourable blood–brain barrier‐permeation properties. Structure–activity relationships demonstrated that the ability of these nicotinoyl hydrazones to increase NAD+ was dependent on the electron‐withdrawing or electron‐donating substituents on the aldehyde‐ or ketone‐derived moiety. Aldehyde‐derived hydrazones containing the ONO donor set and electron‐donating groups were required for NAD+ donation and low cytotoxicity.Conclusions and ImplicationsThe nicotinoyl hydrazones, particularly SNH6, have the potential to act as multifunctional therapeutic agents and delivery vehicles for NAD+ precursors for AD treatment.
• Synthesis, magnetic and electrochemical properties of binuclear copper(II) complexes of pyridoxal hydrazones
  作者：Madan Mohan、Niranjan K. Gupta、Munesh Kumar、Narendra K. Jha、William E. Antholine

  DOI：10.1016/s0020-1693(00)85517-6

  日期：1992.7

  variable temperature magnetic moments, however, indicate the presence of very weak intramolecular antiferro- magnetic interactions (−2J ≈~90 cm−1) in between the copper(II) centers in the complexes. The ESR spectral data at 77 K are characteristic of binuclear CuCu complexes and exhibit a seven-line pattern in the low field gl region. The cyclic voltammograms of each complex showed two oxidation waves

  摘要合成了吡new醛苯甲酰hydr（PBH），吡ido醛邻羟基苯甲酰hydr（PHBH），吡ido吡啶甲基酰yl（PPH），吡ido烟酰yl（PNH）和吡x异烟酰yl（PINH）合成的双核铜（II）配合物。分析，磁性，光谱，ESR和电化学方法。所有复合物在室温下均表现出正常的磁矩。然而，可变温度磁矩表明在配合物中的铜（II）中心之间存在非常弱的分子内反铁磁相互作用（-2J≈〜90 cm-1）。在77 K处的ESR光谱数据是双核CuCu络合物的特征，并且在低场gl区域表现出七线模式。
• Dephosphorylation of pyridoxal 5′‐phosphate‐derived Schiff bases in the presence of bovine alkaline phosphatase
  作者：George Gamov、Anastasia Murekhina、Viktor Aleksandriiskii

  DOI：10.1002/kin.21541

  日期：2022.1

  The present paper reports on the study of the dephosphorylation of pyridoxal 5′-phosphate and four derived hydrazones (containing the residues of pyrazine, 2-furan, 2-thiophene, 3-pyridine carboxylic acids) induced by bovine alkaline phosphatase from intestinal mucosa at 298.2 K and pH 10 (0.05 m Tris–HCl buffer). We observed and discussed characteristic changes in the UV–vis and fluorescent spectra

  本论文报道了由牛碱性磷酸酶从肠粘膜中诱导的 5'-磷酸吡哆醛和四种衍生腙（含有吡嗪、2-呋喃、2-噻吩、3-吡啶羧酸残基）的去磷酸化作用的研究。 298.2 K 和 pH 10（0.05 m Tris-HCl 缓冲液）。我们观察并讨论了底物的 UV-vis 和荧光光谱的特征变化。计算酶促脱磷酸的 Michaelis-Menten 参数。碱性磷酸酶在腙存在下的稳定性得到证实。分析了 Zn(II) 复合物与吡哆醛 5'-磷酸衍生腙的去磷酸化作用。