N'-(1-phenylethylidene)isonicotinohydrazide | 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: N'-(1-phenylethylidene)isonicotinohydrazide
• 英文别名: N-(1-phenylethylideneamino)pyridine-4-carboxamide
• CAS: 4813-13-2
• 化学式: C₁₄H₁₃N₃O
• 分子量: 239.277
• InChiKey: KBNUSICRUXGHRJ-UHFFFAOYSA-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：

  N'-(1-phenylethylidene)isonicotinohydrazide 以 甲苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Khan, Mohsin Abbas; Akhtar, Samar; Shahid, Khadija, Acta poloniae pharmaceutica, 2018, vol. 75, # 1, p. 265 - 271

  摘要：

  DOI：
• 作为产物：
  描述：

  异烟酸 在 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成 N'-(1-phenylethylidene)isonicotinohydrazide
  参考文献：
  名称：

  Khan, Mohsin Abbas; Akhtar, Samar; Shahid, Khadija, Acta poloniae pharmaceutica, 2018, vol. 75, # 1, p. 265 - 271

  摘要：

  DOI：

文献信息

• Copper catalyzed cyanomethylation reaction of 4-thiazolidinone
  作者：Prakashsingh M. Chauhan、Mayur I. Morja、Manjoorahmed Asamdi、Kishor H. Chikhalia

  DOI：10.1016/j.tetlet.2020.152601

  日期：2020.12

  An effective copper catalyzed Cross Dehydrogenative Coupling (CDC) reaction of 4-thiazolidinones with acetonitrile has been developed. The described strategy undergoes radical pathway by employing copper, oxidant and easily available acetonitrile as a cyanomethyl source. Various cyanomethylated 4-thiazolidinone derivatives were obtained easily and conveniently in moderate to good yield by employing

  已经开发了4-噻唑烷酮与乙腈的有效铜催化的交叉脱氢偶联（CDC）反应。所描述的策略通过使用铜，氧化剂和易于获得的乙腈作为氰甲基源而经历自由基途径。通过使用该方法，容易且方便地以中等至良好的产率获得各种氰基甲基化的4-噻唑烷酮衍生物。基板范围和优化已适当进行。通过不同的氧化剂，催化剂和各种添加剂进行了优化。
• Syntheses and structural studies on picolinoyl, nicotinoyl and isonicotinoyl hydrazone derivatives of dicyclopentadienylzirconium(IV)
  作者：Vinita Srivastava、Om P. Pandey、Soumitra K. Sengupta、Satish C. Tripathi

  DOI：10.1016/s0022-328x(00)98997-6

  日期：1986.6

  The reactions of dicyclopentadienylzirconium(IV) dichloride with picolinoyl, nicotinoyl and isonicotinoyl hydrazones derived from the appropriate acid hydrazides and acetone, acetophenone, salicylaldehyde or o-hydroxyacetophenone, have been studied in anhydrous tetrahydrofuran or dichloromethane in the presence or absence of amine using different molar ratios. Tentative structural coclusions are drawn

  在无水四氢呋喃或二氯甲烷中，在存在或不存在胺的情况下，研究了无水四氢呋喃或二氯甲烷中二环戊二烯基二氯化锆（IV）与衍生自适当酸酰肼和丙酮，苯乙酮，水杨醛或邻羟基苯乙酮的吡啶甲酸，烟碱和异烟酰肼的反应。比率。根据元素分析，电导率，磁矩和光谱数据（电子，红外和1 H NMR）为反应产物绘制了暂定的结构共轭关系。这些配体表现为中性或去质子化的螯合剂。配位行为取决于介质的pH，取代基的性质以及hydr基相对于吡啶氮核的位置。
• Heterocyclization of Isoniazid: Synthesis and Antimicrobial Activity of Some new Pyrimidine 1, 3-Thiazole, 1, 2, 4-Thiadiazole, and 1, 2, 4-Triazole, Derivatives Derived from Isoniazid
  作者：mona farhan、mohammed assy

  DOI：10.21608/ejchem.2018.4427.1393

  日期：2018.9.12

  ammonium thiocyanate, cyclohexanone and acetophenone to give 1,2,4-triazole thione 10, hydrazones 9 and 12 was studied. Treatment of hydrazones 9 and 12 with carbon disulfide and aryl isothiocyanates gave 1,3,4-thiadiazolidine 11 and 1,2,4-triazole thione derivatives 13a, b. The antimicrobial activity of these new compounds has been evaluated against 6 microbial strains. Some of the newly synthesized

  异烟酰胺（1）（异烟肼）与肉桂酰基异硫氰酸酯（2）的反应得到肉桂酰基硫代氨基脲化合物3。在乙酸，乙醇钠，硫酸，氯乙酰氯和次氯酸钠和氢氧化钠中的乙酸铅处理3 4，三唑噻嗪5、1,3,4-噻二唑6、1,3-噻唑7和1,2,4-噻二唑8。研究了异烟肼1对硫氰酸铵，环己酮和苯乙酮的反应活性，得到1,2,4-三唑硫酮10，9和12。用二硫化碳和异硫氰酸芳基酯处理9和12，得到1,3,4-噻二唑烷11和1,2,4-三唑硫酮衍生物13a，b。这些新化合物的抗微生物活性已针对6种微生物菌株进行了评估。
• Synthesis and Antifungal Activity <i>In Vitro</i> of Isoniazid Derivatives against Histoplasma capsulatum var. capsulatum
  作者：Rossana de Aguiar Cordeiro、Francisca Jakelyne de Farias Marques、Rebecca de Aguiar Cordeiro、Marcos Reinaldo da Silva、Angela Donato Maia Malaquias、Charlline Vládia Silva de Melo、Jair Mafezoli、Maria da Conceição Ferreira de Oliveira、Raimunda Sâmia Nogueira Brilhante、Marcos Fábio Gadelha Rocha、Tereza de Jesus Pinheiro Gomes Bandeira、José Júlio Costa Sidrim

  DOI：10.1128/aac.01654-13

  日期：2014.5

  Histoplasmosis is a severe infection that affects millions of patients worldwide and is endemic in the Americas. Amphotericin B (AMB) and itraconazole are highly effective for the treatment of severe and milder forms of the disease, but AMB is toxic, and the bioavailability of itraconazole is erratic. Therefore, it is important to investigate new classes of drugs for histoplasmosis treatment. In this study, a series of nine isoniazid hydrazone derivatives were synthesized and evaluated for their antifungal activities in vitro against the dimorphic fungus Histoplasma capsulatum var. capsulatum . The drugs were tested by microdilution in accordance with CLSI guidelines. The compound N ′-(1-phenylethylidene)isonicotinohydrazide had the lowest MIC range of all the compounds for the yeast and filamentous forms of H. capsulatum . The in vitro synergy of this compound with AMB against the planktonic and biofilm forms of H. capsulatum cells was assessed by the checkerboard method. The effects of this hydrazone on cellular ergosterol content and membrane integrity were also investigated. The study showed that the compound alone is able to reduce the ergosterol content of planktonic cells and can alter the membrane permeability of the fungus. Furthermore, the compound alone or in combination with AMB showed inhibitory effects against mature biofilms of H. capsulatum . N ′-(1-Phenylethylidene)isonicotinohydrazide alone or combined with AMB might be of interest in the management of histoplasmosis.

  摘要 组织胞浆菌病是一种严重的传染病，影响着全球数百万患者，在美洲呈地方性流行。两性霉素 B（AMB）和伊曲康唑对治疗重度和轻度组织胞浆菌病非常有效，但两性霉素 B 有毒性，而伊曲康唑的生物利用度不稳定。因此，研究治疗组织胞浆菌病的新型药物非常重要。本研究合成了一系列九种异烟肼腙衍生物，并对它们的抗真菌活性进行了以下评估 体外 针对二形真菌 荚膜组织胞浆菌 变种 荚膜组织胞浆菌 .根据 CLSI 指南，对药物进行了微量稀释测试。化合物 N ′-(1-苯基亚乙基)异烟酰肼在所有化合物中对酵母和丝状荚膜梭菌的 MIC 范围最低。 噬菌体 .体外 体外 该化合物与 AMB 的体外协同作用对浮游型和生物膜型的 细胞的协同作用。 细胞的协同作用。还研究了这种腙对细胞麦角甾醇含量和膜完整性的影响。研究表明，单独使用这种化合物能够降低浮游细胞的麦角甾醇含量，并能改变真菌的膜渗透性。此外，该化合物单独使用或与 AMB 联合使用都能对成熟的荚膜真菌生物膜产生抑制作用。 H. capsulatum . N ′-（1-苯基亚乙基）异烟酰肼单独使用或与 AMB 联用可能对组织胞浆菌病的治疗有一定意义。
• Preparation and antitubercular activities in vitro and in vivo of novel Schiff bases of isoniazid
  作者：Michael J. Hearn、Michael H. Cynamon、Michaeline F. Chen、Rebecca Coppins、Jessica Davis、Helen Joo-On Kang、Abigail Noble、Becky Tu-Sekine、Marianne S. Terrot、Daniella Trombino

  DOI：10.1016/j.ejmech.2009.05.009

  日期：2009.10

  Structural modification of the frontline antitubercular isonicotinic acid hydrazide (INH) provides lipophilic adaptations (3-46) of the drug in which the hydrazine moiety of the parent compound has been chemically blocked from the deactivating process of N-2-acetylation by N-arylaminoacetyl transferases. As a class, these compounds show high levels of activity against Mycobacterium tuberculosis in vitro and in tuberculosis-infected macrophages. They provide strong protection in tuberculosis-infected mice and have low toxicity. With some representatives of this class achieving early peak plasma concentrations approximately three orders of magnitude above minimum inhibitory concentration, they may serve as tools for improving our understanding of INH-based treatment modalities, particularly for those patients chronically underdosed in conventional INH therapy. (C) 2009 Elsevier Masson SAS. All rights reserved.