(E)-N′-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide | 732-91-2

• 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: (E)-N′-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide
• 英文别名: N′-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide；(E)-N'-(5-bromo-2-hydroxybenzaldehyde)isonicotinohydrazide；(E)-N’-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide；(E)-N'-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide；isonicotinic acid-(5-bromo-2-hydroxy-benzylidenehydrazide)；Isonicotinsaeure-(5-brom-2-hydroxy-benzylidenhydrazid)；2-Hydroxy-5-brom-benzaldehyd-isonicotinoylhydrazon；Isonicotinsaeure-5-bromsalicyliden-hydrazon；N'-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide；N-[(E)-(5-bromo-2-hydroxyphenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 732-91-2
• 化学式: C₁₃H₁₀BrN₃O₂
• 分子量: 320.145
• InChiKey: UFNBDHGHPMABQB-LZYBPNLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 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：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N′-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide 、 二苯基二氯化锡 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以75.8%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 、 5-溴水杨醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以75%的产率得到(E)-N′-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide
  参考文献：
  名称：

  (E)-N'-(5-bromo-2-hydroxybenzylidene)isonicotinohydrazide的合成、晶体结构、hirshfeld表面分析、DFT计算、抗糖尿病活性和分子对接研究

  摘要：

  摘要 在目前的工作中，新合成的化合物 E)-N'-(5-溴-2-羟基亚苄基)异烟酰肼 (2) 已被合成并通过 IR、1H 和 13C NMR、ESI-MS 和单晶 X 射线表征。使用实验和理论方法进行衍射分析。使用密度泛函理论 (DFT) 计算通过 B3LYP 方法和 6-31++G (d,p) 基组，探索了标题分子的分子几何、振动频率、前沿分子轨道 (HOMO-LUMO) 能量和热力学性质. 此外，研究了 Hirshfeld 和分子静电势 (MEP) 表面分析。此外，还评估了标题化合物对 α-葡萄糖苷酶和 α-淀粉酶的体外抗糖尿病活性。最后，在标题配体和 1CLV/2ZE0 酶之间进行了分子对接研究。对接计算表明2-2ZE0复合物比2-1CLV复合物更稳定，因为它具有最好的抑制作用，其总能量得分等于-108.68 kcal/mol。对接结果表明，主要的相互作用力是氢键和范德瓦尔斯相互作用。

  DOI：

  10.1016/j.molstruc.2020.128800

文献信息

• Synthesis and characterization of a series of isoniazid hydrazones. Spectroscopic and theoretical study
  作者：Verónica Ferraresi-Curotto、Gustavo A. Echeverría、Oscar E. Piro、Reinaldo Pis-Diez、Ana C. González-Baró

  DOI：10.1016/j.molstruc.2016.12.018

  日期：2017.4

  Abstract A family of hydrazones of isoniazid and a group of hydroxybenzalaldehydes (vanillin, 5-bromovanillin, 5-chlorosalicylaldehyde and 5-bromosalicylaldehyde) were obtained and fully characterized. The results, including theoretical data, are comparatively analyzed along with the already reported hydrazone of o -vanillin. The crystal structures of three compounds were determined. The hydrazones

  摘要 获得了一系列异烟肼腙和一组羟基苯甲醛（香兰素、5-溴香兰素、5-氯水杨醛和5-溴水杨醛）并对其进行了充分表征。结果，包括理论数据，与已经报道的邻香兰素腙进行了比较分析。测定了三种化合物的晶体结构。由卤代醛得到的腙是同晶型的，并且彼此具有手性。(pyr)NH + ⋯Cl - 和 OwH⋯Cl - 键进一步稳定了结构。香草醛腙显示出不同于先前报道的构象异构体。相邻的分子通过 OH⋯N(pyr) 键相互连接，产生近乎平面的聚合物结构。在气相中搜索构象空间并优化几何形状，包括通过 DFT 的溶剂效应。结果扩展到描述 5-溴香草醛腙。在计算计算的帮助下测量和分配了 FTIR、NMR 和电子光谱。
• Novel oxo–peroxo W(VI) Schiff base complex: synthesis, SC-XRD, spectral characterization, supporting on chloromethylated polystyrene, and catalytic oxidation of sulfides
  作者：Hadi Kargar、Majid Moghadam、Leyla Shariati、Nourollah Feizi

  DOI：10.1007/s13738-022-02517-8

  日期：2022.7

  oxo–peroxo tungsten(VI) Schiff base complex, [WO(O2)L(CH3OH)], as a homogeneous catalyst for sulfoxidation was synthesized by treating WO3 in H2O2 with an ONO–tridentate Schiff base ligand. The complex was characterized by FT-IR, UV–Vis, 1H NMR and 13C1H} NMR spectroscopy. Moreover, the structure of the crystalline tungsten(VI) complex was further investigated by SC-XRD. The crystal structure analysis revealed

  通过在 H 2 O 2中用 ONO-三齿 Schiff处理 WO 3合成一种新型的氧代-过氧钨 (VI) 席夫碱配合物 [WO(O 2 )L(CH 3 OH)] 作为磺化氧化的均相催化剂碱基配体。该配合物通过 FT-IR、UV-Vis、1 H NMR 和13 C 1进行了表征H}核磁共振光谱。此外，通过SC-XRD进一步研究了结晶钨（VI）配合物的结构。晶体结构分析表明，W配合物的配位环境为七配位，被扭曲的五边形-双锥体中的配位体的ONO组占据。此外，固定在氯甲基化聚苯乙烯上的 W(VI) 席夫碱在非均相条件下显示出高效的硫化物氧化。通过 FT-IR、漫反射 UV-Vis、XRD、FE-SEM、EDX 和 ICP-AES 技术系统地表征了多相催化剂。相比之下，固定化非均相催化剂表现出优于其均相对应物的活性，并且可以重复使用多次。
• Sah; Peoples, Journal of the American Pharmaceutical Association (1912), 1954, vol. 43, p. 513,514
  作者：Sah、Peoples

  DOI：——

  日期：——
• 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.
• Tsukamoto; Yuhi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 706
  作者：Tsukamoto、Yuhi

  DOI：——

  日期：——