3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridinecarboxaldehyde semicarbazone | 781-66-8

• 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: 3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridinecarboxaldehyde semicarbazone
• 英文别名: pyridoxal-semicarbazide Schiff base；pyridoxal semicarbazone；[[3-Hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methylideneamino]urea
• CAS: 781-66-8
• 化学式: C₉H₁₂N₄O₃
• 分子量: 224.219
• InChiKey: IGAITZANDFTCMJ-UHFFFAOYSA-N

物化性质

• 熔点：
  230 °C (decomp)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  chromium(III) nitrate nonahydrate 、 3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridinecarboxaldehyde semicarbazone 以 乙醇 为溶剂， 反应 24.0h， 以38%的产率得到[Cr(PLSC)(PLSC-H)](NO₃)₂*H₂O
  参考文献：
  名称：

  Transition metal complexes with thiosemicarbazide-based ligands. Part 63. Syntheses, structures and physicochemical characterization of the first chromium(III) complexes with pyridoxal semi- and thiosemicarbazones

  摘要：

  With pyridoxal semi-/thiosemicarbazones (PLSC/PLTSC) ligands for the first time chromium complexes were obtained. In the reaction of ethanolic solution of Cr(NO3)(3) and K-3[Cr(NCS)(6)] and the ligands in mole ratio 1:1 or 1:2, the following complexes were formed: [Cr(PLSC)(PLSC-H)](NO3)(2)center dot H2O (1), K[Cr(PLSC-H) (NCS)(3)]center dot EtOH (2), [Cr(PLTSC)(PLTSC-H)](NO3)(2)center dot 2H(2)O (3), [Cr(PLTSC)(2)](NO3)(3) (4) and [Cr(PLTSC)(NCS)(3)]center dot 2H(2)O (5). All the complexes have mer-octahedral structure which in the cases of the complexes 2, 4 and 5 was proved by single-crystal X-ray diffraction analysis. The Schiff bases coordinate in the usual tridentate ONX manner (X = O/S; PLSC/PLTSC). The pyridoxalic fragment is zwitter ion regardless of the form of the coordinated ligands: neutral (keto/thion) and monoanionic (enolic/thiolic). In addition to the above complexes, X-ray crystallography was used to characterize neutral and protonated forms of PLSC, i.e., PLSC center dot 2H(2)O and PLSC center dot HNCS, the latter one being obtained as a by-product of the reaction of formation of the complex 2 using K-3[Cr(NCS)(6)] and PLSC in the mole ratio 1:2. The X-ray analyses of these ligand forms have shown that in the case of PLSC center dot HNCS the ligators O-phenolic, N-azomethine, O-keto due to strong hydrogen O2-H center dot center dot center dot N3 bond are placed in cis-position to each other (pro-binding conformation) which is not the case with PLSC center dot 2H(2)O. The compounds are characterized thoroughly by also IR/UV-Vis spectral analyses, electrochemical and thermal methods. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.09.017
• 作为产物：
  描述：

  [Cu(pyridoxal-semicarbazide Schiff base)Cl₂]·2H₂O 在 L-组氨酸 作用下， 以 水 为溶剂， 反应 0.67h， 生成 3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridinecarboxaldehyde semicarbazone
  参考文献：
  名称：

  打开基于ESIPT的组氨酸化学传感器：在尿液分析和活细胞成像中的应用

  摘要：

  摘要含有基于激发态分子内质子转移（ESIPT）的维生素B6辅助因子的荧光传感器[Cu（LH2）Cl2]·2H2O [LH2为吡ido醛-半氨基肼基希夫碱]是一种选择性的“裸眼”荧光传感器通过配体置换法在水性介质中在pH 7.4下测定-组氨酸。Uv-Vis分光光度法和循环伏安法也可用于通过Cu（II）络合物检测1-组氨酸。DFT计算还支持感测现象。荧光成像研究表明，Cu（II）-络合物可用于可视化活细胞中的细胞内组氨酸。我们的化学传感器还可用于定量测定尿液中的组氨酸。它可作为对组氨酸进行生理和病理评估的有用工具。它还显示了“浸入式”方法的高效率。

  DOI：

  10.1016/j.ica.2018.06.017

文献信息

• Synthesis, Crystal Structure, Theoretical Calculations, Antibacterial Activity, Electrochemical Behavior, and Molecular Docking of Ni(II) and Cu(II) Complexes with Pyridoxal-Semicarbazone
  作者：Violeta Jevtovic、Njood Alshammari、Salman Latif、Abdulmohsen Khalaf Dhahi Alsukaibi、Jamal Humaidi、Tahani Y. A. Alanazi、Fahad Abdulaziz、Samah I. Matalka、Nebojša Đ. Pantelić、Milica Marković、Aleksandra Rakić、Dušan Dimić

  DOI：10.3390/molecules27196322

  日期：——

  New Ni (II) and Cu (II) complexes with pyridoxal-semicarbazone were synthesized and their structures were solved by X-ray crystallography. This analysis showed the bis-ligand octahedral structure of [Ni(PLSC-H)2]·H2O and the dimer octahedral structure of [Cu(PLSC)(SO4)(H2O)]2·2H2O. Hirshfeld surface analysis was employed to determine the most important intermolecular interactions in the crystallographic

  合成了新的 Ni (II) 和 Cu (II) 与吡哆醛-缩氨基脲的配合物，并通过 X 射线晶体学解析了它们的结构。该分析表明[Ni(PLSC-H) 2 ]·H 2 O的双配体八面体结构和[Cu(PLSC)(SO 4 )(H 2 O)] 2 ·2H 2 O的二聚八面体结构。 Hirshfeld 表面分析用于确定晶体结构中最重要的分子间相互作用。使用密度泛函理论和自然键轨道分析进一步检查了这两种配合物的结构。研究了在两种化合物存在下亚甲基蓝的光催化分解。两种化合物都对大肠杆菌和金黄色葡萄球菌，最低抑制浓度与氯霉素相似。所获得的复合物导致自由基物质的形成，正如在二氯荧光素-二乙酸酯的实验中所证明的那样。推测这是抗菌和光催化活性的机理途径。化合物的循环伏安图显示金属离子的还原峰。一项分子对接研究表明，Ni(II) 复合物对 Janus 激酶 (JAK) 表现出有希望的活性，可作为炎症性疾病、癌症和免疫疾病的潜在疗法。
• Dibromo(pyridoxal semicarbazone-κ³<i>N</i>¹,<i>O</i>³,<i>O</i>^3′)copper(II)
  作者：Dejan Poleti、Ljiljana Karanović、Vukadin M. Leovac、Violeta S. Jevtović

  DOI：10.1107/s0108270103001215

  日期：2003.3.15

  The title compound, dibromo(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridinecarboxaldehyde semicarbazone-kappa(3)N(1), O-3, -O-3')copper(II), [CuBr2(C9H12N4O3)], consists of discrete complex units with the tridentate pyridoxal semicarbazone ligand as a zwitterion in an almost planar configuration. The Cu-II ions are in a distorted square-pyramidal coordination, with the equatorial Br atom at a distance of 2.4017 (6) Angstrom and the apical Br atom at a distance of 2.6860 (6) Angstrom.
• Turn on ESIPT based chemosensor for histidine: Application in urine analysis and live cell imaging
  作者：Chandrima Das、Bholanath Pakhira、Arnold L. Rheingold、Shyamal Kumar Chattopadhyay

  DOI：10.1016/j.ica.2018.06.017

  日期：2018.10

  intramolecular proton transfer (ESIPT) based fluorescent sensor [Cu(LH2)Cl2]·2H2O [LH2 is pyridoxal-semicarbazide Schiff base] is used as a selective “naked-eye” fluorescent sensor of l -histidine at pH 7.4 in aqueous media via the ligand displacement approach. Uv-Vis spectrophotometry and cyclic voltammetry can also be used to detect l -histidine by the Cu(II)-complex. The DFT calculation also supports

  摘要含有基于激发态分子内质子转移（ESIPT）的维生素B6辅助因子的荧光传感器[Cu（LH2）Cl2]·2H2O [LH2为吡ido醛-半氨基肼基希夫碱]是一种选择性的“裸眼”荧光传感器通过配体置换法在水性介质中在pH 7.4下测定-组氨酸。Uv-Vis分光光度法和循环伏安法也可用于通过Cu（II）络合物检测1-组氨酸。DFT计算还支持感测现象。荧光成像研究表明，Cu（II）-络合物可用于可视化活细胞中的细胞内组氨酸。我们的化学传感器还可用于定量测定尿液中的组氨酸。它可作为对组氨酸进行生理和病理评估的有用工具。它还显示了“浸入式”方法的高效率。
• Transition metal complexes with thiosemicarbazide-based ligands. Part 63. Syntheses, structures and physicochemical characterization of the first chromium(III) complexes with pyridoxal semi- and thiosemicarbazones
  作者：Ljiljana S. Vojinović-Ješić、Ljiljana S. Jovanović、Vukadin M. Leovac、Mirjana M. Radanović、Marko V. Rodić、Berta Barta Holló、Katalin Mészásaros Szécsényi、Sonja A. Ivković

  DOI：10.1016/j.poly.2015.09.017

  日期：2015.11

  With pyridoxal semi-/thiosemicarbazones (PLSC/PLTSC) ligands for the first time chromium complexes were obtained. In the reaction of ethanolic solution of Cr(NO3)(3) and K-3[Cr(NCS)(6)] and the ligands in mole ratio 1:1 or 1:2, the following complexes were formed: [Cr(PLSC)(PLSC-H)](NO3)(2)center dot H2O (1), K[Cr(PLSC-H) (NCS)(3)]center dot EtOH (2), [Cr(PLTSC)(PLTSC-H)](NO3)(2)center dot 2H(2)O (3), [Cr(PLTSC)(2)](NO3)(3) (4) and [Cr(PLTSC)(NCS)(3)]center dot 2H(2)O (5). All the complexes have mer-octahedral structure which in the cases of the complexes 2, 4 and 5 was proved by single-crystal X-ray diffraction analysis. The Schiff bases coordinate in the usual tridentate ONX manner (X = O/S; PLSC/PLTSC). The pyridoxalic fragment is zwitter ion regardless of the form of the coordinated ligands: neutral (keto/thion) and monoanionic (enolic/thiolic). In addition to the above complexes, X-ray crystallography was used to characterize neutral and protonated forms of PLSC, i.e., PLSC center dot 2H(2)O and PLSC center dot HNCS, the latter one being obtained as a by-product of the reaction of formation of the complex 2 using K-3[Cr(NCS)(6)] and PLSC in the mole ratio 1:2. The X-ray analyses of these ligand forms have shown that in the case of PLSC center dot HNCS the ligators O-phenolic, N-azomethine, O-keto due to strong hydrogen O2-H center dot center dot center dot N3 bond are placed in cis-position to each other (pro-binding conformation) which is not the case with PLSC center dot 2H(2)O. The compounds are characterized thoroughly by also IR/UV-Vis spectral analyses, electrochemical and thermal methods. (C) 2015 Elsevier Ltd. All rights reserved.