2-pyridylcarboxaldehyde isonicotinoyl hydrazone | 15017-32-0

• 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: 2-pyridylcarboxaldehyde isonicotinoyl hydrazone
• 英文别名: pyridine-2-carboxaldehyde isonicotinoyl hydrazone；N'-[(1E)-pyridin-2-ylmethylene]isonicotinohydrazide；N-[(E)-pyridin-2-ylmethylideneamino]pyridine-4-carboxamide
• CAS: 15017-32-0
• 化学式: C₁₂H₁₀N₄O
• 分子量: 226.238
• InChiKey: WRHZTTISLCLBBE-OQLLNIDSSA-N

物化性质

• 溶解度：
  >33.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  67.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-pyridylcarboxaldehyde isonicotinoyl hydrazone 以 乙腈 为溶剂， 反应 0.33h， 以61%的产率得到(Z)-N'-(pyridin-2-ylmethylene)isonicotinic hydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  异烟酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-pyridylcarboxaldehyde isonicotinoyl hydrazone
  参考文献：
  名称：

  N-acylhydrazones confer inhibitory efficacy against New Delhi metallo-β-lactamase-1

  摘要：

  DOI：

  10.1016/j.bioorg.2021.105138

文献信息

• [EN] METAL ION CHELATORS AND THERAPEUTIC USE THEREOF<br/>[FR] CHELATEURS D'IONS METALLIQUES ET LEUR UTILISATION THERAPEUTIQUE
  申请人：UNISEARCH LTD

  公开号：WO2004069801A1

  公开（公告）日：2004-08-19

  The present invention relates to compounds which are capable of chelating metal ions. In particular, the present invention relates to (thio)semicarbazone compounds and (thio)hydrazone compounds which are capable of chelating metal ions, including iron ions. Also disclosed are therapeutic use of such compounds and/or their metal ion complexes, including methods of treating diseases associated with cell proliferation.

  本发明涉及能够螯合金属离子的化合物。具体而言，本发明涉及能够螯合金属离子，包括铁离子的（硫）氨基甲酮类化合物和（硫）醛肟类化合物。还披露了这些化合物及/或它们的金属离子络合物的治疗用途，包括治疗与细胞增殖相关的疾病的方法。
• Synthesis and analgesic activity of novel N-acylarylhydrazones and isosters, derived from natural safrole##This paper represents contribution # 36 of the LASSBio, UFRJ (Br.) (LASSBio, http://acd.ufrj.br/≈pharma/lassbio); For contribution # 35, see [24].
  作者：Patrícia C. Lima、Lídia M. Lima、Kelli Cristine M. da Silva、Paulo Henrique O. Léda、Ana Luisa P. de Miranda、Carlos A.M. Fraga、Eliezer J. Barreiro

  DOI：10.1016/s0223-5234(00)00120-3

  日期：2000.2

  Anew series of antinociceptive compounds belonging to the N-acylarylhydrazone (NAH) class were synthesized from natural safrole (7). The most analgesic derivative represented by 10f, [(4'-N,N-dimethylaminobenzylidene-3-(3', 4'-methylenedioxyphenyl)propionylhydrazine], was more potent than dipyrone and indomethacin, used as standards. The NAH compounds described herein were structurally planned by molecular

  从天然黄樟脑合成了一系列新的N-酰基芳基hydr（NAH）类抗伤害感受化合物（7）。以10f表示的最止痛衍生物，[（4'-N，N-二甲基氨基苄叉基-3-（3'，4'-亚甲基二氧苯基）丙酰肼]]比双嘧啶和消炎痛更有效，用作标准品。我们通过分子杂交和经典生物立体异构策略对先前报道的止痛NAH进行结构规划，以鉴定N-酰基芳基hydr部分的药效学作用并研究这些系列中的构效关系（SAR）。
• Syntheses, characterization and crystal structures of potassium and barium complexes of a Schiff base ligand with different anions
  作者：BHAVESH PARMAR、KAMAL KUMAR BISHT、PRATYUSH MAITI、PARIMAL PAUL、ERINGATHODI SURESH

  DOI：10.1007/s12039-014-0701-1

  日期：2014.9

  2-pyridylcarboxaldehyde isonicotinoylhydrazone (L) and its discrete complexes with K+ and Ba2+ have been reported. L forms isostructural dinuclear complexes with K+ when bromide and iodide were employed as counter anions. However, a monomeric complex in the case of Ba2+ with existence of coordinated as well as lattice perchlorate counter anions was observed. All compounds were characterized by single crystal

  已经报道了O，N，N'-供体配体，2-吡啶基甲醛异烟酰2-（L）及其与K +和Ba 2+的离散复合物的新假多晶型物。当溴化物和碘化物用作抗衡阴离子时，L与K +形成同构的双核配合物。然而，在Ba 2+的情况下，观察到单体配合物存在配位的以及晶格的高氯酸盐抗衡阴离子。所有化合物均通过单晶X射线分析和其他物理化学技术表征。详细介绍了所有化合物的结构分析和光谱特征。 所述schiiff碱配体O，N，N'-腙供体配体（2- pyridylcarboxaldehyde isonicotinoylhydrazone）（新psuedopolymorpic形式大号）和它们与碱金属和碱土金属配合物已经通过各种物理-化学技术如FTIR研究， TGA，PXRD和固态吸收光谱，包括X射线晶体学。当使用溴化物和碘化物作为抗衡阴离子时，L与K +形成同构双核络合物，而与Ba 2+形成的单核络合物既具有配位阴离子也具有未配位的高氯酸盐抗衡阴离子。
• Iron chelators and uses thereof
  申请人：University of Queensland

  公开号：US06989397B1

  公开（公告）日：2006-01-24

  The present invention provides 2-pyridylcarboxaldehyde isonicotinoyl hydrazone (PCIH) analogues suitable for use as an in vivo iron chelators, the PCIH analogue having Formula 1: wherein R1 is an aromatic or heterocyclic group and R2 is either H or OH; isomers thereof or salts thereof; pharmaceutical compositions containing the analogues; and uses of the analogues in the treatment of iron-overload diseases.

  本发明提供适用于体内铁螯合剂的2-吡啶甲醛异烟肼酰肼（PCIH）类似物，其中PCIH类似物具有公式1：其中R1是芳香族或杂环基团，R2是H或OH；其异构体或盐；含有这些类似物的制药组合物；以及这些类似物在治疗铁过载疾病中的用途。
• Heteronuclear, mixed-metal Ag(<scp>i</scp>)–Mn(<scp>ii</scp>) coordination polymers with bridging N-pyridinylisonicotinohydrazide ligands: synthesis, crystal structures, magnetic and photoluminescence properties
  作者：Rahman Bikas、Hassan Hosseini-Monfared、Vera Vasylyeva、Joaquín Sanchiz、Javier Alonso、Jose Manuel Barandiaran、Christoph Janiak

  DOI：10.1039/c4dt01390e

  日期：——

  Mixed-metal dicyanoargentate-bridged coordination polymers of Ag(I)–Mn(II) have been prepared and their structure and magnetic properties were determined. Reaction of manganese(II) chloride and potassium dicyanoargentate(I) with (X)(pyridin-2-ylmethylene)isonicotinohydrazide ligands (HL1 X = Ph, HL2 X = Me, HL3 X = H) produced the coordination polymer 2D-[Mn(μ-L1)(Cl)(μ-NCAgCN)Mn0.5(CH3OH)]n (1),

  制备了Ag（I）-Mn（II）的混合金属双氰基桥接的配位聚合物，并确定了它们的结构和磁性能。氯化锰（II）和二氰基Argantate钾（I）与（X）（吡啶-2-基亚甲基）异烟酰肼配体（HL 1 X = Ph，HL 2 X = Me，HL 3 X = H）反应生成配位聚合物2D - [锰（μ-L 1）（CL）（μ-NCAgCN）的Mn 0.5（CH 3 OH）] ñ（1），1D - [锰（L 2）（Cl）的（μ-NCAgCN）的Mn 0.5（ CH 3 OH）] CH 3OH} n（2）和[Mn（L 3）（Cl）（μ-NCAgCN）Mn 0.5（CH 3 OH）] n（3），收率高。三核锰（μ-L 1）的Mn（μ-L 1）的Mn}，并将[Ag（CN）2 ] -构建单元形成在一个二维板坯1支中和1D链2。可变温度磁化率测量显示，尽管高自旋Mn（II）离子之间的距离很长[10.4676（12）Å和10