(E)-N′-(1-( pyridin-2-yl)ethylidene)isonicotinohydrazide

• 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′-(1-( pyridin-2-yl)ethylidene)isonicotinohydrazide
• 英文别名: (E)-N′-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide；(E)-N'-(1-(pyridin-2-yl)ethylidene)isonicotinic hydrazide；(E)-N'-[1-(pyridin-2-yl)ethylidene]isonicotinoylhydrazide；(E)-N'-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide；(E)-N'-[1-(pyridin-2-yl)ethylidene]isonicotinohydrazide；N'-[(1E)-1-(pyridin-2-yl)ethylidene]pyridine-4-carbohydrazide；N-[(E)-1-pyridin-2-ylethylideneamino]pyridine-4-carboxamide
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: FVEHSUOXXBHVHF-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N′-(1-( pyridin-2-yl)ethylidene)isonicotinohydrazide 以 乙腈 为溶剂， 反应 0.5h， 生成 (Z)-N'-(1-(pyridin-2-yl)ethylidene)isonicotinic hydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  (Z)-N'-(1-(pyridin-2-yl)ethylidene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 3.0h， 生成 (E)-N′-(1-( pyridin-2-yl)ethylidene)isonicotinohydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519

文献信息

• Biomimetic oxo-, dioxo- and oxo-peroxo-hydrazonato-vanadium(iv/v) complexes
  作者：Mannar R. Maurya、Shilpa Khurana、Wenjian Zhang、Dieter Rehder

  DOI：10.1039/b202852m

  日期：——

  Hacpy-bhz II; acpy = acetylpyridine, inh = isonicotinic acid hydrazide, bhz = benzoylhydrazide) in dry methanol to yield the oxovanadium(IV) complexes [VOL(acac)] (HL = I: 1, HL = II: 3). The dioxovanadium(V) complexes [VO2L] (HL = I: 2, HL = II: 4) are obtained by aerial oxidation of 1 and 3 in methanol. Treatment of 1 and 3, or 2 and 4, with H2O2 yields the oxoperoxovanadium(V) complexes [VO(O2)L]

  [VO（acac）2 ]与HL反应（HL是hydrHacpy-inh I或Hacpy-bhz II；acpy =乙酰吡啶，inh = 异烟酸酰肼，bhz =苯甲酰肼）在干燥状态下 甲醇得到氧杂钒（IV）配合物[VOL（acac）]（HL ＝ I：1，HL ＝ II：3）。二氧钒钒（V）络合物[VO 2 L]（HL = I：2，HL = II：4）是通过在1和3中进行空气氧化得到的。甲醇。用H 2 O 2处理1和3或2和4 产生oxoperoxovanadium（V）络合物[VO（O 2）L]（HL = I：5，HL = II：6）。在......的存在下儿茶酚 或者 苯氧肟酸，1和3得到的混合螯合物[VOL（猫）]（HL = 我：7，HL = II：8）或[VOL（BHA）]（HL = 我：9，HL = II：10）。过氧配合物5和6与DMF中的PPh 3进行氧转移反应。在DMF和二甲基亚砜，7，8，9
• Structure-Activity Relationships of Novel Salicylaldehyde Isonicotinoyl Hydrazone (SIH) Analogs: Iron Chelation, Anti-Oxidant and Cytotoxic Properties
  作者：Eliška Potůčková、Kateřina Hrušková、Jan Bureš、Petra Kovaříková、Iva A. Špirková、Kateřina Pravdíková、Lucie Kolbabová、Tereza Hergeselová、Pavlína Hašková、Hana Jansová、Miloslav Macháček、Anna Jirkovská、Vera Richardson、Darius J. R. Lane、Danuta S. Kalinowski、Des R. Richardson、Kateřina Vávrová、Tomáš Šimůnek

  DOI：10.1371/journal.pone.0112059

  日期：——

  Salicylaldehyde isonicotinoyl hydrazone (SIH) is a lipophilic, tridentate iron chelator with marked anti-oxidant and modest cytotoxic activity against neoplastic cells. However, it has poor stability in an aqueous environment due to the rapid hydrolysis of its hydrazone bond. In this study, we synthesized a series of new SIH analogs (based on previously described aromatic ketones with improved hydrolytic

  水杨醛异烟酰yl（SIH）是一种亲脂性三齿铁螯合剂，具有显着的抗氧化剂和对肿瘤细胞适度的细胞毒活性。然而，由于其bond键的快速水解，它在水性环境中的稳定性差。在这项研究中，我们合成了一系列新的SIH类似物（基于先前描述的具有改善的水解稳定性的芳族酮）。就其在血浆中的稳定性，铁螯合功效，氧化还原作用和针对MCF-7乳腺癌细胞的细胞毒性活性，评估了它们的结构活性关系。此外，研究评估了这些螯合剂的细胞毒性及其对过氧化氢诱导的H9c2心肌母细胞氧化损伤提供保护的能力。键还原的配体 或在bond键附近存在庞大的烷基取代基，则表明其生物学活性受到严重限制。溴取代基的引入增加了配体对癌细胞和H9c2心肌母细胞的细胞毒性。当酚环与吡啶交换时（即，将连接位点从O，N，O改变为N，N，O），观察到类似的作用，这导致促氧化作用。相反，与，键相邻的具有长而柔韧的烷基链的化合物对MCF-7乳腺腺癌细胞表现出特定的
• Syntheses, crystal structures and magnetic studies of new manganese(II) coordination polymers with ditopic N-pyridinylisonicotinohydrazide ligand and dicyanamide
  作者：Rahman Bikas、Nader Noshiranzadeh、Lesław Sieroń、Hassan Hosseini-Monfared、Jose Manuel Barandiaran、Tadeusz Lis、Javier Alonso

  DOI：10.1016/j.inoche.2016.03.009

  日期：2016.5

  Abstract Two new coordination polymers of Mn(II) with dicyanamide anion (dca) and isonicotinohydrazone based ligands, [Mn2(L1)2(dca)2(CH3OH)2]·H2O}n (1) and [Mn2(L2)2(μ-dca)2]n (2), were synthesized and characterized by elemental analyses and spectroscopic methods where HL1 = (E)-N′-(phenyl(pyridin-2-yl)methylene)isonicotinohydrazide and HL2 = (E)-N′-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide

  摘要 Mn(II) 与双氰胺阴离子 (dca) 和异烟腙基配体的两种新型配位聚合物，[Mn2(L1)2(dca)2(CH3OH)2]·H2O}n (1) 和 [Mn2(L2) 2(μ-dca)2]n (2)，通过元素分析和光谱方法合成和表征，其中 HL1 = (E)-N'-(苯基(吡啶-2-基)亚甲基)异烟酰肼和 HL2 = (E )-N'-(1-(吡啶-2-基)亚乙基)异烟酰肼。1 和 2 的红外光谱显示双氰胺配体的特征伸缩振动带为三个带。化合物的结构通过 X 射线衍射分析表征，表明异烟腙配体作为双位配体并通过 N2O 供体组和异烟碱部分的吡啶基与锰离子配位。磁化率测量研究表明高自旋 Mn(II) 离子之间存在反铁磁耦合。2 的反铁磁耦合强于 1，这是由于 Mn(II) 离子通过前者中的双氰胺桥连接。
• Assembly of anion-controlled cadmium(II) coordination polymers from the use of 2-acetyl-pyridyl-isonicotinoylhydrazone
  作者：F.A. Afkhami、A.A. Khandar、J.M. White、A. Guerri、A. Ienco、J.T. Bryant、N. Mhesn、C. Lampropoulos

  DOI：10.1016/j.ica.2016.12.009

  日期：2017.3

  tetradentate ligand in 2 acts as a linker and leads to the formation of a one-dimensional coordination polymer. The CH 3 COO − in 1 and SCN − in 3 and 4 , further act as bridges, forming two-dimensional coordination polymers ( 1 and 3) and a three-dimensional network ( 4 ). Structural diversity is thus induced by the anions, due to the variable steric hindrance they impose as well as differing bridging capacity;

  利用基于四齿吡啶的席夫碱配体，即2-乙酰基-吡啶基-异烟碱基yl（HL）和不同的阴离子（CH 3 COO-，N 3-，SCN-）合成了四种Cd（II）配位聚合物。产物[Cd 2（L）2（CH 3 COO）2]·C 2 H 5 OH} n（1），[Cd 1.5（L）（CH 3 COO）（N 3）（H 2 O） ]·C 2 H 5 OH} n（2），[Cd（HL）（SCN）2]·CH 3 OH} n（3）和[Cd 3（HL）2（SCN）6] n（4）用单晶X射线衍射，红外光谱和发光研究对其进行了表征。1和2中的配体被单去质子化，并以烯醇式（N–NC–O）配位至镉中心，而化合物3和4中的配体以中性酮体形式（N–NH–CO）配位。2中的四齿配体起着连接剂的作用，并导致一维配位聚合物的形成。CH 3 COO-in 1和SCN-in 3和4进一步充当桥，形成二维配位聚合物（1和3）和三维网络（4
• Heteronuclear, mixed-metal Ag(<scp>i</scp>)–Mn(<scp>ii</scp>) coordination polymers with bridging N-pyridinylisonicotinohydrazide ligands: synthesis, crystal structures, magnetic and photoluminescence properties
  作者：Rahman Bikas、Hassan Hosseini-Monfared、Vera Vasylyeva、Joaquín Sanchiz、Javier Alonso、Jose Manuel Barandiaran、Christoph Janiak

  DOI：10.1039/c4dt01390e

  日期：——

  Mixed-metal dicyanoargentate-bridged coordination polymers of Ag(I)–Mn(II) have been prepared and their structure and magnetic properties were determined. Reaction of manganese(II) chloride and potassium dicyanoargentate(I) with (X)(pyridin-2-ylmethylene)isonicotinohydrazide ligands (HL1 X = Ph, HL2 X = Me, HL3 X = H) produced the coordination polymer 2D-[Mn(μ-L1)(Cl)(μ-NCAgCN)Mn0.5(CH3OH)]n (1),

  制备了Ag（I）-Mn（II）的混合金属双氰基桥接的配位聚合物，并确定了它们的结构和磁性能。氯化锰（II）和二氰基Argantate钾（I）与（X）（吡啶-2-基亚甲基）异烟酰肼配体（HL 1 X = Ph，HL 2 X = Me，HL 3 X = H）反应生成配位聚合物2D - [锰（μ-L 1）（CL）（μ-NCAgCN）的Mn 0.5（CH 3 OH）] ñ（1），1D - [锰（L 2）（Cl）的（μ-NCAgCN）的Mn 0.5（ CH 3 OH）] CH 3OH} n（2）和[Mn（L 3）（Cl）（μ-NCAgCN）Mn 0.5（CH 3 OH）] n（3），收率高。三核锰（μ-L 1）的Mn（μ-L 1）的Mn}，并将[Ag（CN）2 ] -构建单元形成在一个二维板坯1支中和1D链2。可变温度磁化率测量显示，尽管高自旋Mn（II）离子之间的距离很长[10.4676（12）Å和10