N'-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N'-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide
• 英文别名: N’-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-3-carbohydrazone；(E)-N’-(2'-hydroxy-3'-methoxybenzylidene)nicotinohydrazide；(E)-N′(2-hydroxy-3-methoxybenzylidene)nicotinohydrazide；nicotinic acid-(2-hydroxy-3-methoxy-benzylidenehydrazide)；Nicotinsaeure-(2-hydroxy-3-methoxy-benzylidenhydrazid)；N'-[(E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-3-carbohydrazide；N-[(E)-(2-hydroxy-3-methoxyphenyl)methylideneamino]pyridine-3-carboxamide
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: DCBGFHCZZYSUBC-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N'-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide 、 二正丁基氧化锡 反应 8.0h， 以83%的产率得到
  参考文献：
  名称：

  Organotin(IV) complexes derived from Schiff base N’-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-3-carbohydrazone: Synthesis, in vitro cytotoxicities and DNA/BSA interaction

  摘要：

  Five organotin(IV) hydrazone compounds have been synthesized from N'-[(1E)-(2-hydroxyl-3-methoxyphenyl) methylidene]pyridine-3-carbohydrazone and the corresponding organotin(IV). Solid state structures of five complexes were determined by elemental analysis, IR, NMR spectroscopy and for 1, 2, 3, 4 and 5 single crystal X-ray diffraction analysis. For compounds 4 and 5, structural analysis shows that each complex is a monomer with the tin atom five-coordinated in a distorted trigonal bipyramid chelating by the Schiff base ligand in an enolic tridentate fashion. Fascinatingly, in compounds 1, 2 and 3, structural analysis of them shows that each complex is a centrosymmetric trimers, in which the central Sn atom adopts six-coordinated geometry and the other Sn atom adopts five-coordinated geometry. In vitro cytotoxicities of five compounds on three human drug resistant tumor cells lines (A549, HeLa and MCF-7) were assessed by MTT assay. The interaction of the complexes with calf thymus DNA (CT-DNA) has been explored by absorption titration method, which revealed that complexes interact with CT-DNA through groove-binding and partial intercalation of the extended planar ligand with the DNA base stack. Furthermore, the protein fluorescence quenching studies reveal that there are strong binding interactions between compounds and bovine serum albumins (BSA). Studies reveal that di-n-butyltin(IV) complexes 2 and 4 with significant antiproliferative effects in the cells show stronger DNA/ BSA interaction than the other complexes. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2015.12.041
• 作为产物：
  描述：

  3-吡啶甲酰肼 、 邻香草醛 以 甲醇 为溶剂， 反应 3.0h， 以87%的产率得到N'-(2-hydroxy-3-methoxyphenylmethylidene)-3-pyridinecarbohydrazide
  参考文献：
  名称：

  用于在热和超声条件下制备苯并咪唑、苯并恶唑和苯并噻唑的新型钒和钼席夫碱配合物的合成、表征和催化潜力

  摘要：

  合成了一种源自 3-甲氧基水杨醛和烟碱酰肼的新型 ONO-三齿席夫碱配体 (H 2 L)，并通过元素分析、FT-IR、1 H NMR、13 C NMR、UV-Vis 和粉末 XRD 研究进行表征。然后，氧钒（V）和二氧钼（VI）席夫碱络合物，VOL和MoO 2L, 也用不同的技术制备和表征。此外，研究了这两种配合物在回流条件下以及通过超声辐照合成苯并咪唑、苯并恶唑和苯并噻唑的催化活性。结果揭示了该方法的几个优点，包括产品收率高、反应时间短、后处理简单、操作简单、反应条件环保，以及避免使用有毒催化剂和溶剂的绿色方面。 图形摘要

  DOI：

  10.1007/s00706-021-02780-0

文献信息

• Comparative studies on conventional and solvent-free synthesis toward hydrazones: application of PXRD and chemometric data analysis in mechanochemical reaction monitoring
  作者：Jana Pisk、Tomica Hrenar、Mirta Rubčić、Gordana Pavlović、Vladimir Damjanović、Jasna Lovrić、Marina Cindrić、Višnja Vrdoljak

  DOI：10.1039/c7ce02136d

  日期：——

  chemometric study using principal component analysis for mechanochemical synthesis monitoring was implemented for the first time to provide an insight into the reaction profiles. A thoughtful combination of ex situ powder X-ray diffraction and chemometric analysis was essential to identify a stepwise mechanism for the hydrazone formation via an intermediate phase. In five investigated reactions the first

  the的合成是通过常规方法和无溶剂方法，使用相应的酰肼（异烟肼，烟碱酰肼，2-氨基苯甲酰肼或4-氨基苯甲酰肼）和适当的醛（水杨醛，3-甲氧基水杨醛或4-甲氧基水杨醛）进行的。专门用于溶剂多态性或多态性筛选的系统研究导致形成了十二种新的晶型，其中八种通过单晶X射线衍射法。在所有研究的结构中，分子都组装成无尽的超分子链，不连续的环，环或网的链。还应用了采用液体辅助研磨的机械化学合成方法，发现烟碱和异烟碱基易于从其相应的前体中形成。首次进行了使用主成分分析进行机械化学合成监测的化学计量学研究，以提供对反应曲线的深入了解。异位粉末X射线衍射和化学计量分析的周到结合对于确定通过via形成formation的逐步机理至关重要中间阶段。在五个调查的反应中，第一个主要成分至少占总方差的75％，而在两个反应的情况下，这一成分占总方差的69.72和46.23％。还评估了hydr在体外的细胞毒性活性。所有化合物
• Xanthine oxidase inhibitory activity of nicotino/isonicotinohydrazides: A systematic approach from in vitro , in silico to in vivo studies
  作者：Humaira Zafar、Muhammad Hayat、Sumayya Saied、Momin Khan、Uzma Salar、Rizwana Malik、M. Iqbal Choudhary、Khalid Mohammed Khan

  DOI：10.1016/j.bmc.2017.02.044

  日期：2017.4

  involved in regulation of serum uric acid, xanthine oxidase (XO) is the best pharmacological target to control the levels of serum uric acid as it catalyzes the final steps in uric acid production. In the current study, a systemic search for the inhibitors of xanthine oxidase, starting from synthesis to in vitro screening and leading to in vivo studies is presented. Benzylidene nicotino/isonicotinohydrazides

  生活方式和饮食习惯的改变导致全球高尿酸血症的患病率增加。高尿酸血症的作用不再局限于痛风，而在CVD，高血压，代谢综合征和关节炎的进展中起着核心作用。在涉及调节血清尿酸的不同因素中，黄嘌呤氧化酶（XO）是控制血清尿酸水平的最佳药理学靶标，因为它催化了尿酸生产的最终步骤。在当前的研究中，从合成到体外筛选，再到体内研究，对黄嘌呤氧化酶抑制剂进行了系统的研究。通过用取代的芳族醛处理烟碱/异烟碱酰肼来合成苄叉烟碱/异烟碱酰肼（1-54），并通过EI-MS和1H NMR进行表征。还进行了元素分析。首先使用体外光谱XO抑制试验筛选所有合成化合物的黄嘌呤氧化酶抑制活性。与标准药物别嘌呤醇IC50 = 2.00±0.01μM相比，发现其中22种衍生物的IC50值为0.96至330.4μM。对五种活性最高的化合物（8、35、36、39和45）进行了动力学研究，其IC50值在0.96至54.8μM之间，具有抑制
• Design, synthesis and in vitro antimalarial activity of an acylhydrazone library
  作者：Patricia Melnyk、Virginie Leroux、Christian Sergheraert、Philippe Grellier

  DOI：10.1016/j.bmcl.2005.09.058

  日期：2006.1

  A library of acylhydrazone iron chelators was synthesized and tested for its ability to inhibit the growth of a chloroquine-resistant strain of Plasmodium falciparum. Some of these new compounds are significantly more active than desferrioxamine DFO, the iron chelator in widespread clinical use and also than the most effective chelators. (c) 2005 Elsevier Ltd. All rights reserved.
• Roboter lackieren mit 2K-Technik
  作者：Frank Reiter

  DOI：10.1007/bf03251522

  日期：2001.12
• Structural and spectroscopic characteristics of aroylhydrazones derived from nicotinic acid hydrazide
  作者：N. Galić、B. Perić、B. Kojić-Prodić、Z. Cimerman

  DOI：10.1016/s0022-2860(00)00703-1

  日期：2001.1

  Aroylhydrazones derived from salicylaldehyde, o-vanillin and nicotinic acid hydrazide have been synthesized and characterized on the basis of NMR, IR and UV/Vis spectral data. The crystal and molecular structure of N'-salicylidene-3-pyridine-carbohydrazide has been determined by X-ray diffraction. (C) 2001 Elsevier Science B.V. All rights reserved.