isonicotinic acid-(1-phenyl-ethylidenehydrazide) | 4813-13-2

• 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: isonicotinic acid-(1-phenyl-ethylidenehydrazide)
• 英文别名: N′-[(1E)-1-phenylethylidene]isonicotinohydrazide；isonicotinic acid-(E)-(1-phenylethylidene)hydrazide；(E)-N'-(1-phenylethylidene)isonicotinic hydrazide；Isonicotinsaeure-(1-phenyl-aethylidenhydrazid)；Acetophenon-；1-Isonicotinoyl-2-(α-methyl-benzyliden)-hydrazin；N'-(1-phenylethylidene)isonicotinohydrazide；N-[(E)-1-phenylethylideneamino]pyridine-4-carboxamide
• CAS: 4813-13-2
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: KBNUSICRUXGHRJ-LFIBNONCSA-N

物化性质

• 熔点：
  172-173 °C
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.07
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isonicotinic acid-(1-phenyl-ethylidenehydrazide) 以 乙腈 为溶剂， 反应 0.42h， 生成 (Z)-N'-(1-phenylethylidene)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-phenylethylidene)isonicotinic hydrazide 以 乙腈 为溶剂， 反应 0.5h， 生成 isonicotinic acid-(1-phenyl-ethylidenehydrazide)
  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

• Synthesis, characterization and pharmacological evaluation of (E)-N′-(substituted-benzylidene)isonicotinohydrazide derivatives as potent anticonvulsant agents
  作者：Manav Malhotra、Vikramdeep Monga、Sagun Sharma、Jainendra Jain、Abdul Samad、James Stables、Aakash Deep

  DOI：10.1007/s00044-011-9739-5

  日期：2012.9

  also evaluated in the minimal clonic seizure model and exhibited potent anticonvulsant activity with lower neurotoxicity. Among all synthesized derivatives, analogue 3a was found to exhibit protection in MES and scPTZ seizure models. This study proved that isonicotinoyl hydrazides synthesized by condensing isoniazid with various aldehydes and ketones displayed moderate to potent anticonvulsant activity

  在无水乙醇和催化量的冰醋酸的存在下，通过将其与不同的取代醛，苯乙酮和二苯甲酮偶联，合成了一系列（E）-N '-（取代亚苄基）异烟酰肼衍生物。通过红外，1 H NMR，13等多种光谱技术对所有合成的化合物进行了确认和表征。13 C NMR和质谱研究。使用各种癫痫发作模型（例如最大电击诱发的癫痫发作（MES）和皮下戊四氮（scPTZ））以30、100和300 mg / kg体重的剂量进行所有惊厥化合物的抗惊厥评估，并发现抗惊厥活性为0.5给药后的h和4 h时间间隔。化合物1A（ë） - ñ '-2 -亚苄基异烟酰肼，1克（ë） - ñ '-2-乙氧基苯亚甲基异烟酰肼，1K（ë） - ñ '-3- flourobenzylidene异烟肼和图3a（ë） -N'-二苯基亚甲基异烟肼在MES模型中显示出保护作用，表明这些化合物具有预防癫痫扩散的作用，剂量为300 mg / kg，并在0.5 h时显示
• Complexation studies of N′-[(1E)-1-phenylethylidene]isonicotinohydrazide: An aroylhydrazone Schiff base and lanthanides
  作者：Yuimi Varam、Lonibala Rajkumari

  DOI：10.1016/j.molliq.2016.11.098

  日期：2017.2

  constants of the complex formation equilibria which follow the order: Pr < Nd < Gd < Tb < Ho. The thermodynamic parameters (ΔG, ΔH, and ΔS) of protonation and complexation reactions are all negative suggesting the spontaneous, exothermic, of unfavorable entropy and enthalpy-driven reactions. Actual synthesis and characterization of Tb3 +-PHeH complex, confirmed the veracity of the complex formation equilibria

  用光谱和电位技术研究了N '-[（1E）-1-苯基亚乙基]异烟酰肼（PHeH）与三价Pr，Nd，Gd，Tb和Ho离子的相互作用。Tb 3 +和PHeH在乙醇和固体Tb 3 + -PHeH复合物中的光致发光研究表明，PHeH对Tb 3 +发光没有敏化作用。研究了不同条件下PHeH的吸收谱带和不同摩尔比的Nd 3 + -PHeH的吸收谱带。在不同的温度下以恒定的离子强度I  = 0.1 mol·dm -3 KNO 3进行1：4 Ln / PHeH摩尔比的电位滴定在二氧六环水溶液介质中的溶解度显示出复合物形成平衡的中等热力学稳定性常数，该常数遵循以下顺序：Pr
• Structural insights into the hexamorphic system of an isoniazid derivative
  作者：D. Hean、T. Gelbrich、U. J. Griesser、J. P. Michael、A. Lemmerer

  DOI：10.1039/c5ce00275c

  日期：——

  The compound isonicotinic acid (E)-(1-phenylethylidene)hydrazide exists in 6 different structural forms isolated through complex manipulations on a Kofler hot stage.

  化合物异烟酸 (E)-(1-苯乙烯基亚肼)存在6种不同的结构形式，通过对Kofler热台的复杂操作分离得到。
• Antimycobacterial compounds and method for making the same
  申请人：Hearn Michael J.

  公开号：US06846933B1

  公开（公告）日：2005-01-25

  The present invention relates to novel antimycobacterial compounds and in particular to antimycobacterial compounds comprised of Schiff base, diacylhydrazine, sulfur-containing diacylhydrazine and oxadiazoline congeners of isonicotinic acid hydrazide. This invention further relates to processes for their preparation, to intermediates useful in their preparation, to their use as therapeutic agents and to pharmaceutical compositions containing them.

  本发明涉及新型抗结核杆菌化合物，特别是包括席夫碱、二酰肼、含硫二酰肼和异烟酸酰肼的噁唑啉同系物的抗结核杆菌化合物。本发明还涉及它们的制备方法，制备过程中有用的中间体，它们作为治疗剂的用途以及包含它们的制药组合物。
• RUBBER COMPOSITION AND PNEUMATIC TIRES
  申请人：Bridgestone Corporation

  公开号：EP0909788A1

  公开（公告）日：1999-04-21

  A rubber composition prepared by compounding 0.05 to 20 parts by weight of at least one selected from substituted hydrazide compounds represented by the following Formulas (I) to (IV) per 100 parts by weight of a rubber component comprising at least one rubber selected from the group consisting of natural rubber and synthetic rubber, and a pneumatic tire using the same: wherein A represents one selected from the group consisting of an aromatic group which may have a substituent, a hydantoin ring which may have a substituent, and a saturated or unsaturated linear hydrocarbon having 1 to 18 carbon atoms; Y represents hydrogen, an amino group, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, an alkenyl group, an aromatic group, a pyridyl group or hydrazino group; and R1 to R11 each represent hydrogen, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group or an aromatic group.

  一种橡胶组合物，其制备方法是每 100 重量份由至少一种选自天然橡胶和合成橡胶组的橡胶组成的橡胶组分中混入 0.05 至 20 重量份的至少一种选自下式(I)至(IV)所代表的取代酰肼化合物，以及使用该组合物的充气轮胎： 其中 A 代表选自芳香基团（可具有取代基）、海因环（可具有取代基）和具有 1 至 18 个碳原子的饱和或不饱和线性烃；Y 代表氢、氨基、具有 1 至 18 个碳原子的烷基、环烷基、烯基、芳香基、吡啶基或肼基；R1 至 R11 分别代表氢、具有 1 至 18 个碳原子的烷基、环烷基或芳香基。