2-pyridylcarboxaldehyde p-aminobenzoylhydrazine | 158833-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-pyridylcarboxaldehyde p-aminobenzoylhydrazine
• 英文别名: 2-pyridinecarbaldehyde(4′-aminobenzoyl)hydrazone；PCAH；2-pyridinecarbaldehyde-4'-aminobenzoyl hydrazone monohydrate；4-amino-N-(pyridin-2-ylmethylideneamino)benzamide
• CAS: 158833-86-4
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: XSICXHHIZPFXFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 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：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  iron(II) perchlorate hexahydrate 、 2-pyridylcarboxaldehyde p-aminobenzoylhydrazine 在 Et₃N 作用下， 以 三乙胺 、 乙腈 为溶剂， 生成 [bis(2-pyridinecarbaldehyde (4'-aminobenzoyl)hydrazonate)iron(II)] hydrate
  参考文献：
  名称：

  dra螯合剂用于治疗铁超负荷疾病：铁配位化学和生物活性。

  摘要：

  潜在的三齿配体2-吡啶甲醛异烟酰yl（HPCIH）及其类似物是一类新兴的口服有效铁螯合剂，对治疗铁超载疾病显示出巨大的希望。本文中，我们对HPCIH类似物的Fe配位化学进行了广泛的研究，包括这些螯合剂的第一个晶体学表征的Fe（II）配合物。与大多数其他临床上有效的铁螯合剂不同，HPCIH类似物结合Fe（II）而不结合Fe（III）。实际上，这些螯合剂形成低旋转双配体Fe（II）配合物，尽管NMR表明该配合物接近高旋转/低旋转交叉。所有的Fe配合物都显示出高电位的Fe（III / II）氧化还原对（> 500 mV vs. NHE）和在水性或混合的水性/有机溶剂中的循环伏安法是不可逆的，因为在氧化时会发生快速水合反应。许多HPCIH类似物在诱导Fe从细胞中流出以及防止细胞从血清Fe转运蛋白转铁蛋白中吸收Fe方面显示出很高的活性。作为一类配体，这些螯合剂在减少铁从转铁蛋白中摄取比诱导从细胞中动

  DOI：

  10.1039/b704102k
• 作为产物：
  描述：

  吡啶-2-甲醛 、 4-氨基苯甲酰肼 在 甲酸 作用下， 以 二甲基亚砜 为溶剂， 生成 2-pyridylcarboxaldehyde p-aminobenzoylhydrazine
  参考文献：
  名称：

  Mechanistic differences between in vitro assays for hydrazone-based small molecule inhibitors of anthrax lethal factor

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2006.07.004

文献信息

• A Multi-Stimuli-Responsive Fe(II) SCO Complex Based on an Acylhydrazone Ligand
  作者：Xiu-Qin Chen、You-De Cai、Wei Jiang、Guo Peng、Jing-Kun Fang、Jun-Liang Liu、Ming-Liang Tong、Xin Bao

  DOI：10.1021/acs.inorgchem.8b02922

  日期：2019.1.22

  An Fe(II) SCO complex based on an acylhydrazone ligand with an amino functional group has been prepared. The complex is able to dissociate and regather upon protonation and deprotonation, in both solid state and solution, accompanied by spin state switching, marked change of color, and distinct solubility in water. Moreover, the complex shows distinct magnetic responses toward formaldehyde and protic

  制备了基于具有氨基官能团的酰基hydr配体的Fe（II）SCO配合物。该复合物能够在固态和溶液中在质子化和去质子化时解离和聚集，伴随着自旋态转换，显着的颜色变化和在水中的独特溶解性。而且，由于氨基官能位与那些化学物质的不同亲合力，该络合物对甲醛，质子和非质子溶剂表现出不同的磁响应。
• COLORIMETRIC DETECTOR
  申请人：Fundación Imdea Nanociencia

  公开号：EP3789761A1

  公开（公告）日：2021-03-10

  The present invention is related to the detection of formaldehyde concentrations in the air by using a coordination polymer, which comprises repeating coordination complexes with an octahedral geometry, wherein said coordination complex comprises iron (II), at least one ligand comprising an amino moiety; wherein the coordination polymer further comprises counter-ions comprising an aromatic moiety; for the identification and/or quantification of formaldehyde.

  本发明涉及使用配位聚合物检测空气中的甲醛浓度，配位聚合物由具有八面体几何形状的重复配位络合物组成，其中所述配位络合物包括铁（II）、至少一个由氨基组成的配体；配位聚合物还包括由芳香族分子组成的反离子；用于识别和/或定量甲醛。
• [EN] COLORIMETRIC DETECTOR<br/>[FR] DÉTECTEUR COLORIMÉTRIQUE
  申请人：FUND IMDEA NANOCIENCIA

  公开号：WO2021043982A1

  公开（公告）日：2021-03-11

  The present invention is related to the detection of formaldehyde concentrations in the air by using a coordination polymer, which comprises repeating coordination complexes with an octahedral geometry, wherein said coordination complex comprises iron (II), at least one ligand comprising an amino moiety; wherein the coordination polymer further comprises counter-ions; for the identification and/or quantification of formaldehyde.
• Hydrazone chelators for the treatment of iron overload disorders: iron coordination chemistry and biological activity
  作者：Paul V. Bernhardt、Piao Chin、Philip C. Sharpe、Des R. Richardson

  DOI：10.1039/b704102k

  日期：——

  number of the HPCIH analogues show high activity at inducing Fe efflux from cells and also at preventing Fe uptake by cells from the serum Fe transport protein transferrin. As a class of ligands, these chelators are more effective at reducing Fe uptake from transferrin than inducing Fe mobilisation from cells. This may be related to their ability to intercept Fe(II) after its release from transferrin within

  潜在的三齿配体2-吡啶甲醛异烟酰yl（HPCIH）及其类似物是一类新兴的口服有效铁螯合剂，对治疗铁超载疾病显示出巨大的希望。本文中，我们对HPCIH类似物的Fe配位化学进行了广泛的研究，包括这些螯合剂的第一个晶体学表征的Fe（II）配合物。与大多数其他临床上有效的铁螯合剂不同，HPCIH类似物结合Fe（II）而不结合Fe（III）。实际上，这些螯合剂形成低旋转双配体Fe（II）配合物，尽管NMR表明该配合物接近高旋转/低旋转交叉。所有的Fe配合物都显示出高电位的Fe（III / II）氧化还原对（> 500 mV vs. NHE）和在水性或混合的水性/有机溶剂中的循环伏安法是不可逆的，因为在氧化时会发生快速水合反应。许多HPCIH类似物在诱导Fe从细胞中流出以及防止细胞从血清Fe转运蛋白转铁蛋白中吸收Fe方面显示出很高的活性。作为一类配体，这些螯合剂在减少铁从转铁蛋白中摄取比诱导从细胞中动
• 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.