N-(2-isonicotinoylhydrazine-carbonothioyl)benzamide | 21531-83-9

• 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-(2-isonicotinoylhydrazine-carbonothioyl)benzamide
• 英文别名: N-(2-isonicotinoylhydrazine-1-carbonothioyl)benzamide；4-benzoyl-1-isonicotinoylthiosemicarbazide；1-(4-Pyridinecarbonyl)-4-benzoylthiosemicarbazide；N-[(pyridine-4-carbonylamino)carbamothioyl]benzamide
• CAS: 21531-83-9
• 化学式: C₁₄H₁₂N₄O₂S
• mdl: MFCD01424138
• 分子量: 300.341
• InChiKey: ZPFCLBUPXVZSJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  光气 、 N-(2-isonicotinoylhydrazine-carbonothioyl)benzamide 在 sodium acetate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以90%的产率得到N-[5-oxo-4-(pyridine-4-carbonyl)-1,3,4-thiadiazol-2-yl]benzamide
  参考文献：
  名称：

  Preparation of new 5-aroylamino substituted 3-nicotinoyl/isonicotinoyl-1,3,4-thiadiazol-2(3H)-ones with anti-inflammatory activity

  摘要：

  A series of 1,3,4-thiadiazol-2(3H)-ones (2a-j) with a nicotinoyl/isonicotinoyl group in position 3 and an aroylamino substituent in position 5 of the ring was prepared and evaluated for antipyretic and anti-inflammatory activities. All the title compounds and in particular 2e, 2i and 2j exhibited anti-inflammatory activity and were devoid of antipyretic properties. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00073-1
• 作为产物：
  描述：

  异烟肼 、 苯甲酰基异硫氰酸酯 以 乙腈 为溶剂， 反应 1.5h， 以89.3%的产率得到N-(2-isonicotinoylhydrazine-carbonothioyl)benzamide
  参考文献：
  名称：

  新型酰基硫脲衍生物：合成、抗真菌活性、基因毒性、类药物和分子对接筛选

  摘要：

  合成了九种新型酰基硫脲。它们的特性和纯度通过 LC-MS 光谱确认；通过元素分析、IR、1Н和13C NMR光谱阐明了每种结构。应用其抗真菌潜力的体外筛选，可以选择三种物质（3、5 和 6）显示出对 11 种真菌和 3 种具有植物致病意义的疫霉菌株的高活性。使用沙门氏菌反向诱变试验分析基因毒性，作为药物相似性、亲脂性和前沿分子轨道计算的评估，这些化合物具有低毒性特征。分子对接研究表明 14α-脱甲基酶 (CYP51) 和 N-肉豆蔻酰转移酶 (NMT) 可能是真菌生长抑制的靶点。就构效关系 (SAR) 讨论了这些发现。

  DOI：

  10.1002/ardp.201800275

文献信息

• Poly[bis(μ-4-benzoyl-1-isonicotinoylthiosemicarbazide-κ²<i>N</i>:<i>S</i>)dichloridocadmium(II)]
  作者：Yu-Bo Wang、Tong-Hen Pan、Qian Liang、Dong-Sheng Liu、Chang-Cang Huang

  DOI：10.1107/s0108270110011455

  日期：2010.5.15

  The asymmetric unit of the title complex, [CdCl2(C14H12N4O2S)(2)](n), consists of one Cd-II ion located on the crystallographic inversion centre, one 4-benzoyl-1-isonicotinoylthiosemicarbazide ligand and one chloride ligand. The central Cd-II ion adopts a distorted octahedral coordination geometry formed by two pyridyl N atoms of two ligands, two S atoms of two other ligands and two chloride ligands. The thiosemicarbazide ligands act as bridges, linking the metal ions into a two-dimensional layered structure parallel to the bc plane. Intermolecular N-H center dot center dot center dot O hydrogen bonds and C-H center dot center dot center dot pi interactions exist between adjacent layers.
• Spectral, optical, and cytotoxicity studies on<i>N</i>-(2-isonicotinoylhydrazine-carbonothioyl)benzamide and its metal complexes
  作者：Nasser Mohammed Hosny、Heba M. Mahmoud、Mohamed H. Abdel-Rhman

  DOI：10.1002/hc.21415

  日期：2018.3

  AbstractThe ligand N‐(2‐isonicotinoylhydrazine‐carbonothioyl)benzamide (H3L) and its metal complexes with Co(II), Ni(II), Cu(II), and Zn(II) acetates have been synthesized. The synthesized compounds have been characterized by elemental analyses, FT‐IR, UV‐Visible spectra, 1H‐NMR, 13C‐NMR, ESR, MS, effective magnetic moments, molar conductance, and thermal analyses. The free organic ligand exists in the keto form, but in the metal complexes, it forms chelates with the metal ions in the enol form. The measured optical band gap (Eg) values confirmed the presence of direct electronic transition and the semiconductivity of the current compounds. The ligand and its Zn(II) complex were examined as cytotoxic agents against HePG‐2 and HCT‐116 and showed. H3L exhibited strong cytotoxicity, while Zn complex showed moderate activity.
• Preparation of new 5-aroylamino substituted 3-nicotinoyl/isonicotinoyl-1,3,4-thiadiazol-2(3H)-ones with anti-inflammatory activity
  作者：Silvia Schenone、Olga Bruno、Angelo Ranise、Francesco Bondavalli、Walter Filippelli、Giuseppe Falcone、Brunella Piucci、Salvatore Sorrentino

  DOI：10.1016/s0014-827x(98)00073-1

  日期：1998.8

  A series of 1,3,4-thiadiazol-2(3H)-ones (2a-j) with a nicotinoyl/isonicotinoyl group in position 3 and an aroylamino substituent in position 5 of the ring was prepared and evaluated for antipyretic and anti-inflammatory activities. All the title compounds and in particular 2e, 2i and 2j exhibited anti-inflammatory activity and were devoid of antipyretic properties. (C) 1998 Elsevier Science S.A. All rights reserved.
• Novel acyl thiourea derivatives: Synthesis, antifungal activity, gene toxicity, drug-like and molecular docking screening
  作者：Lyudmyla Antypenko、Fatuma Meyer、Olena Kholodniak、Zhanar Sadykova、Tereza Jirásková、Anastasiia Troianova、Vladlena Buhaiova、Surui Cao、Sergiy Kovalenko、Leif-Alexander Garbe、Karl G. Steffens

  DOI：10.1002/ardp.201800275

  日期：2019.2

  Nine novel acyl thioureas were synthesized. Their identities and purities were confirmed by LC‐MS spectra; each structure was elucidated by elemental analysis, IR, 1Н and 13C NMR spectra. Applying an in vitro screening of their antifungal potential, three substances (3, 5, and 6) could be selected as showing high activity against 11 fungi and 3 Phytophthora strains of phytopathogenic significance.

  合成了九种新型酰基硫脲。它们的特性和纯度通过 LC-MS 光谱确认；通过元素分析、IR、1Н和13C NMR光谱阐明了每种结构。应用其抗真菌潜力的体外筛选，可以选择三种物质（3、5 和 6）显示出对 11 种真菌和 3 种具有植物致病意义的疫霉菌株的高活性。使用沙门氏菌反向诱变试验分析基因毒性，作为药物相似性、亲脂性和前沿分子轨道计算的评估，这些化合物具有低毒性特征。分子对接研究表明 14α-脱甲基酶 (CYP51) 和 N-肉豆蔻酰转移酶 (NMT) 可能是真菌生长抑制的靶点。就构效关系 (SAR) 讨论了这些发现。