4-cyanobenzaldehyde isonicotinoyl-hydrazone | 260555-91-7

• 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: 4-cyanobenzaldehyde isonicotinoyl-hydrazone
• 英文别名: N'-(4-cyanobenzylidene)isonicotinohydrazide；N-[(4-cyanophenyl)methylideneamino]pyridine-4-carboxamide
• CAS: 260555-91-7
• 化学式: C₁₄H₁₀N₄O
• 分子量: 250.26
• InChiKey: KPJHKIZXTUPRIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  78.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  高氯酸银水合物 、 4-cyanobenzaldehyde isonicotinoyl-hydrazone 以 甲醇 、 氯仿 为溶剂， 以43%的产率得到poly[[[μ3-N'-(4-cyanobenzylidene)isonicotinohydrazide]silver(I)]perchlorate]
  参考文献：
  名称：

  A grid-like two-dimensional Ag^Icoordination polymer: poly[[[μ₃-N′-(4-cyanobenzylidene)isonicotinohydrazide]silver(I)] perchlorate]

  摘要：

  This study presents new coordinating modes of a Schiff base with three coordinating groups and an interesting two-dimensional framework based on two types of constructing units. In the title compound, {[Ag(C(14)H(10)N(4)O)]ClO(4)}(n), the Ag(I) ion is coordinated by three N atoms and one O atom from three different N'-(4-cyanobenzylidene)isonicotinohydrazide (L) ligands, forming a primary distorted square-planar coordination geometry. Two ligands each bridge two metal centres through one carbonitrile N atom in a monodentate mode and the hydrazide N and O atoms in a bidentate mode to form a small centrosymmetric (2+ 2)-Ag(2)L(2) ring as a principal constructing unit. The pyridyl N atoms from four ligands in four of these small rings coordinate to Ag atoms in adjacent rings to form a large hexanuclear silver grid. A two-dimensional framework of rectangular grids is constructed from these small rings and large grids. Two perchlorate anions are located in each large grid and are bound to the grid by N-H H center dot center dot center dot O hydrogen bonding. Crosslinking between the layers is achieved through long Ag center dot center dot center dot O interactions between the perchlorate anions and Ag atoms in adjacent layers.

  DOI：

  10.1107/s0108270108023585
• 作为产物：
  描述：

  异烟肼 、 4-氰基苯甲醛 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4-cyanobenzaldehyde isonicotinoyl-hydrazone
  参考文献：
  名称：

  Experimental and theoretical study of 4-cyanobenzaldehyde isonicotinoyl-hydrazone monohydrate

  摘要：

  The molecular geometry, vibrational frequencies, gauge-including atomic orbital (CIAO) H-1 and C-13 chemical shift values of 4-cyanobenzaldehyde isonicotinoyl-hydrazone monohydrate in the ground state have been calculated by using the Hartree-Fock (HF) and density functional method (DFT/B3LYP) with 6-31++G(d,p) basis set. Furthermore, this structure has been confirmed by IR, C-13 and H-1 spectroscopy. The results of the optimized molecular structure are presented and compared with the experimental X-ray diffraction. The computed vibration frequencies are used to determine the types of molecular motions associated with each of the experimental bands observed. C-13 and H-1 NMR data were calculated by means of the methods of GIAO, CSGT, and IGAIM. Calculated chemical shift values are compared with the experimental 4-cyanobenzaldehyde isonicotinoyl-hydrazone monohydrate. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.10.011

文献信息

• Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor
  作者：M. Leslie Hanna、Theodore M. Tarasow、Julie Perkins

  DOI：10.1016/j.bioorg.2006.07.004

  日期：2007.2

  A systematically generated series of hydrazones were analyzed as potential inhibitors of anthrax lethal factor. The hydrazones were screened using one UV-based and two fluorescence-based in vitro assays. The study identified several inhibitors with IC50 values in the micromolar range, and importantly, significant differences in the types of inhibition were observed with the different assays. (c) 2006 Elsevier Inc. All rights reserved.