(E)-N'-((2-hydroxynaphthalen-1-yl)methylene)isonicotinohydrazide | 796-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N'-((2-hydroxynaphthalen-1-yl)methylene)isonicotinohydrazide
• 英文别名: N'-[(2-hydroxynaphthalen-1-yl)methylidene]pyridine-4-carbohydrazide；N-[(E)-(2-hydroxynaphthalen-1-yl)methylideneamino]pyridine-4-carboxamide
• CAS: 796-42-9
• 化学式: C₁₇H₁₃N₃O₂
• mdl: MFCD00033110
• 分子量: 291.309
• InChiKey: WQSHHAVECQJKLX-YBFXNURJSA-N

物化性质

• 溶解度：
  溶于DMSO(45mg/ml)；乙醇（10mg/ml加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090
• 储存条件：
  | 温度范围：0-10°C；存储在惰性气体中；防止湿气（吸湿）和受热 |

制备方法与用途

生物活性

AS8351 是一种 KDM5B 抑制剂，能够诱导和维持有活性的染色质标记，从而促进心肌细胞样细胞的产生。

靶点

KDM5B

体外研究

AS8351 能够通过与 α-酮戊二酸 (α-KG) 竞争铁 [Fe(II)] 来影响表观遗传修饰，从而抑制依赖于 α-KG 和铁作为辅助因子的 JmjC 域含组蛋白去甲基酶（JmjC-KDMs）活性。

反应信息

• 作为反应物：
  描述：

  (E)-N'-((2-hydroxynaphthalen-1-yl)methylene)isonicotinohydrazide 、 二甲基二氯化锡 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到
  参考文献：
  名称：

  Synthesis, spectral characterization, crystal structure and antibacterial studies of diorganotin(IV) complexes with isonicotinoyl hydrazone derivatives

  摘要：

  The new diorganotin(IV) complexes R2SnL (L = L-a: R = Me 1, Ph 2; L = L-b: R = Me 3, Ph 4, L = L-c: R = Me 5, Ph 6, Bu 7) have been synthesized by the reaction of the hydrazone ligands N'-(5-bromo-2-hydroxybenzylidene) isonicotinohydrazide (H2La), N'((2-hydroxynaphthalen-1-yl)methylene) isonicotinohydrazide (H2Lb) and N'-(2,4-dihydroxybenzylidene) isonicotinohydrazide (H2L(c)) with diorganotin(IV) dichloride. The synthesised compounds have been investigated by elemental analysis, together with IR, H-1 and Sn-119 NMR spectroscopy. The structures of H2La, H2Lb and 3 have also been confirmed by X-ray crystallography. On the basis of these data, H2La and H2Lb are present in the keto-amine tautomeric form and intermolecular N-H center dot center dot center dot N hydrogen bonds form 1D chain structures. The hydrazone ligands act as tridentate dibasic in the enol form and are coordinated via the imine nitrogen, phenolate and enolate oxygen atoms. The in vitro antibacterial activity of the ligands and their complexes has been evaluated against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria and compared with standard antibacterial drugs. The R2SnLc complexes exhibited greater activities than the other compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2014.04.061
• 作为产物：
  描述：

  异烟肼 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 4.0h， 以74%的产率得到(E)-N'-((2-hydroxynaphthalen-1-yl)methylene)isonicotinohydrazide
  参考文献：
  名称：

  Heteroleptic Oxidovanadium(V) Complexes with Activity against Infective and Non-Infective Stages of Trypanosoma cruzi

  摘要：

  五种异配合物，[VVO(IN-2H)(L-H)]，其中L为8-羟基喹啉衍生物，IN为席夫碱配体，已在固态和溶液状态下合成并表征。这些化合物在Trypanosoma cruzi的表皮马斯蒂哥特和三型马斯蒂哥特以及VERO细胞上进行了评估，作为哺乳动物细胞模型。这些化合物对三型马斯蒂哥特表现出活性，IC50值为0.29-3.02μM。IN配体和新的[VVO2(IN-H)]复合物显示微弱活性。最活性的化合物[VVO(IN-2H)(L2-H)]，其中L2=5-氯-7-碘-8-羟基喹啉，对寄生虫具有良好的选择性，并被选择进行进一步的生物学研究。稳定性研究表明在溶液中存在部分分解。[VVO(IN-2H)(L2-H)]影响细胞来源的三型马斯蒂哥特的感染潜力。确定了寄生虫对钒的摄取量较低，并且在可溶蛋白分数中有优先积累。在将表皮马斯蒂哥特与[VVO(IN-2H)(L2-H)]的10×IC50值孵育后观察到了杀锁效应，并建议治疗后会产生ROS。与DNA：溴化乙锭加合物的荧光竞争测量显示了复合物的中等DNA相互作用。在C. elegans模型上进行的体内毒性研究表明，[VVO(IN-2H)(L2-H)]的浓度高达100μM时没有毒性。这种化合物可能被视为有前景的抗T. cruzi药物，值得进一步研究。

  DOI：

  10.3390/molecules26175375

文献信息

• Electronic Effects of Aromatic Rings on the Catalytic Activity of Dioxidomolybdenum(VI)–Hydrazone Complexes
  作者：Rahman Bikas、Vito Lippolis、Nader Noshiranzadeh、Hossein Farzaneh‐Bonab、Alexander J. Blake、Milosz Siczek、Hassan Hosseini‐Monfared、Tadeusz Lis

  DOI：10.1002/ejic.201601359

  日期：2017.2.10

  peroxide as environmental friendly oxidant. In order to ‎achieve the highest catalytic activity, the effects of important ‎parameters such as solvent, temperature and the molar ratio of ‎oxidant to substrate were optimized. The results indicate that ‎electron-withdrawing substituents on the ligands increase the ‎catalytic activity of dioxidomolybdenum(VI)-hydrazone complexes.‎

  九种二氧化钼 (VI) 配合物是通过 MoO3 与三齿腙席夫碱配体的反应合成的，该配体是从芳香酰肼（3-羟基-2-萘甲酰肼、4-吡啶羧酸酰肼或 2-呋喃羧酸酰肼）和邻羟基醛衍生物（5-碘-2-羟基苯甲醛、2-羟基-1-萘醛或 2-羟基-3-甲氧基苯甲醛）。所有配体和配合物均通过元素分析和光谱方法表征。通过单晶 X 射线衍射分析进一步阐明了七种配合物的结构，表明金属中心存在扭曲的八面体几何形状。光谱和 X 射线分析表明，由于络合时酚类 OH 和酰胺基 NH 基团的去质子化，配体与钼 (VI) 离子配位为双负性配体。这些配合物在作为环境友好型氧化剂的过氧化氢存在下，在环辛烯和茴香硫醚的氧化中用作催化剂。为了达到最高的催化活性，对溶剂、温度和氧化剂与底物的摩尔比等重要参数的影响进行了优化。结果表明配体上的吸电子取代基提高了二氧化钼 (VI)-腙络合物的催化活性。这些配合物在作为环境友好型氧化剂的
• Spectral studies on cobalt(II), nickel(II) and copper(II) complexes of naphthaldehyde substituted aroylhydrazones
  作者：Pramod Kumar Singh、Deo Nandan Kumar

  DOI：10.1016/j.saa.2005.08.014

  日期：2006.7

  A series of new coordination complexes of cobalt(II), nickel(II) and copper(II) with two new aroylhydrazones, 2-hydroxy-1-naphthaldehyde isonicotinoylhydrazone (H(2)L(1)) and 2-hydroxy-1-naphthaldehyde-2-thenoyl-hydrazone (H(2)L(2)) have been synthesized and characterized by elemental analysis, conductance measurements, magnetic susceptibility measurements, (1)H NMR spectroscopy, IR spectroscopy, electronic

  钴（II），镍（II）和铜（II）的一系列新配位配合物与两个新的芳酰hydr，2-羟基-1-萘醛异烟酰yl（H（2）L（1））和2-羟基-1 -萘甲醛-2-thenoyl-hydr（H（2）L（2））已合成并通过元素分析，电导率测量，磁化率测量，（1）H NMR光谱，IR光谱，电子光谱，EPR光谱和热分析。红外光谱表明，配体作为三齿二元供体，通过去质子化的萘氧原子，偶氮甲碱氮原子和烯醇氧原子进行配位。EPR和配体场光谱表明Co（II）和Ni（II）配合物为八面体几何形状，Cu（II）配合物为正方形平面几何形状。
• A three-dimensional manganese(II) coordination polymer: synthesis, structure and catecholase activity
  作者：Prama Bhattacherjee、Partha Mitra、Prasenjit Sarkar、Rohith P. John

  DOI：10.1080/00958972.2020.1740213

  日期：2020.2.1

  Abstract A manganese-based coordination polymer, [Mn2L2(µ-MeOH)2]n (H2L = 2-hydroxy-1-naphthaldehyde isonicotinoylhydrazone) was obtained by self-assembly of 2-hydroxy-1-naphthaldehyde isonicotinoylhydrazone and manganese(II) acetate. The coordination polymer was characterized by IR, EPR and UV–Vis spectroscopy. The single-crystal X-ray diffraction study reveals that the dibasic tridentate ligand (L2−)

  摘要 2-羟基-1-萘醛异烟酰腙和锰(II)自组装得到锰基配位聚合物[Mn2L2(μ-MeOH)2]n(H2L=2-羟基-1-萘醛异烟酰腙)醋酸盐。配位聚合物通过 IR、EPR 和 UV-Vis 光谱进行表征。单晶 X 射线衍射研究表明，二元三齿配体 (L2-) 通过 ONO 供体位点与锰 (II) 结合。两个这样的 [ML] 片段通过 μ2 桥接甲醇 (MeOH) 连接形成二锰物种。每个锰的第六位被异烟酰基的吡啶基N原子占据。这种排列产生式[Mn2L2(μ-MeOH)2]n的多核配合物。锰的配位几何是扭曲的八面体。复合物在 77 K 的 X 波段电子顺磁共振 (EPR) 测量显示六线谱和半场信号，g = 4.88。半场信号表明复合物在溶液状态下的二聚性质。复合物的循环伏安测量显示了可逆的 MnIII/MnII 氧化还原对。该复合物催化 3,5-二叔丁基邻苯二酚转化为相应的邻醌，催化转化率为
• Sah; Peoples, Journal of the American Pharmaceutical Association (1912), 1954, vol. 43, p. 513,514
  作者：Sah、Peoples

  DOI：——

  日期：——
• Synthesis and evaluation of isonicotinoyl hydrazone derivatives as antimycobacterial and anticancer agents
  作者：H. S. Naveen Kumar、Thaigarajan Parumasivam、Fatimah Jumaat、Pazilah Ibrahim、Mohd. Zaini Asmawi、Amirin Sadikun

  DOI：10.1007/s00044-013-0632-2

  日期：2014.1

  A new series of isonicotinoyl hydrazone derivatives (3a-3o) have been synthesized, characterized and evaluated for in vitro antimycobacterial activity against M. tuberculosis H37Rv and two clinical isolates using tetrazolium microplate assay (TEMA). Some of these compounds showed moderate to good antimycobacterial activity at micro molar concentrations. Among them, 3k and 3m were the most potent analogues with an inhibition concentration at 0.59 and 0.65 mu M, respectively, against M. tuberculosis H37Rv compared to parent drug, isoniazid (0.57 mu M). Additionally, all the synthesized compounds were subjected to in vitro anticancer activity against human colorectal cancer cell lines (HCT 116). Compounds 3b and 3l displayed antiproliferative activity at inhibitory concentration 3.1 and 0.29 mu M, respectively, when compared to standard, 5-fluorouracil (5 mu M). These results can be considered as an important start point for the rational design of new leads for antitubercular and anticancer drug discovery.