N'-isonicotinoylbenzenesulfonohydrazide | 16827-12-6

• 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: N'-isonicotinoylbenzenesulfonohydrazide
• 英文别名: N-benzenesulfonyl-N'-isonicotinoyl hydrazine；N-Benzolsulfonyl-N'-isonicotinoyl-hydrazin；N'-(benzenesulfonyl)pyridine-4-carbohydrazide
• CAS: 16827-12-6
• 化学式: C₁₂H₁₁N₃O₃S
• 分子量: 277.304
• InChiKey: UKJCMAQTXOTHNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N'-isonicotinoylbenzenesulfonohydrazide 在 双氧水 、 溶剂黄146 作用下， 生成 N-benzenesulfonyl-N'-(1-oxy-isonicotinoyl)-hydrazine
  参考文献：
  名称：

  31. N-氧化物和相关化合物。第七部分 一些共轭吡啶的过酸氧化

  摘要：

  DOI：

  10.1039/jr9580000150
• 作为产物：
  描述：

  、 苯磺酰氯 在 sodium carbonate 作用下， 以79.4%的产率得到N'-isonicotinoylbenzenesulfonohydrazide
  参考文献：
  名称：

  Benzenesulfonohydrazides inhibiting urease: Design, synthesis, their in vitro and in silico studies

  摘要：

  Keeping in view the therapeutic importance of ureases due to its involvement in different pathological conditions, its inhibition was investigated by newly synthesized benzenesulfonohydrazides. Elemental analysis, IR, H-1 NMR and C-13 NMR spectral studies were performed to elucidate the structure of benzenesulfonohydrazides. In vitro urease enzyme inhibition assay revealed the compound INS-5 was found to be the most potent (IC50 = 1.11 +/- 0.29 mu M) among the tested compounds. The compound INS-2 was competitive inhibitor with Ki value 5.60 mu M while the compounds INS-1 and INS-5 were mixed type of inhibitors with Ki values 4.32 and 2.76 mu M respectively. Ancillary to synthetic studies, DFT and TDDFT calculations at B3LYP/6-311G(d,p) level of theory were performed for comparative analysis of spectroscopic data, frontier molecular orbitals (FMOs), natural bond orbital (NBO) analysis and molecule electrostatic potential (MEP) surface. Overall, experimental findings were supported nicely by corresponding DFT computed results. The NBO analysis confirmed that the presence of hyperconjugative interactions are pivotal cause for stability of investigated compounds. Global reactivity descriptors were also calculated using the energies of FMOs energies. Molecular docking studies were performed to identify the plausible binding mode of the competitive inhibitor. (C) 2020 Published by Elsevier B.V.

  DOI：

  10.1016/j.molstruc.2020.128740

文献信息

• Cucurbituril-resisted acylation of the anti-tuberculosis drug isoniazidvia a supramolecular strategy
  作者：Hang Cong、Chun-Rong Li、Sai-Feng Xue、Zhu Tao、Qian-Jiang Zhu、Gang Wei

  DOI：10.1039/c0ob00114g

  日期：——

  A chemical investigation reveals that the resistance to acylation of an anti-tuberculosis drug, isoniazid is a consequent result of the inclusion or exclusion of cucurbit[n]urils (n = 6 or 7). The 1H NMR spectra analysis shows that the different interaction models of the isoniazid with the two cucurbiturils are dependent on the cavity size of the hosts. Quantum chemistry calculations with density functional theory method indicate that the interaction of the isoniazid with both cucurbiturils is through thermodynamic stabilization in both the gas phase and aqueous solution through hydrogen bonding on the portal carbonyls of the cucurbiturils. Electronic absorption titration spectra suggest the hosts and guest interact in a ratio of 1 : 1 with moderate binding constants. Acylation kinetics of isoniazid with various acylating agents in the presence of the cucurbiturils revealed that resistance is only dependent on the host–isoniazid ratio, and independent on the size of the cucurbiturils and the species of acylating agents.

  一项化学调查显示，抗结核药物异烟肼的酰化抗性是包含或排除葫芦[n]脲（n = 6 或 7）的结果。1H NMR 光谱分析显示，异烟肼与两种葫芦脲的不同相互作用模型取决于宿主的空腔大小。用密度泛函理论方法进行的量子化学计算表明，异烟肼与两种葫芦素的相互作用是通过葫芦素的门户羰基上的氢键在气相和水溶液中实现热力学稳定的。电子吸收滴定光谱表明，宿主和客体的相互作用比例为 1 ：1 的比例相互作用，结合常数适中。异烟肼与各种酰化剂在葫芦素存在下的酰化动力学表明，抗性只取决于宿主与异烟肼的比例，而与葫芦素的大小和酰化剂的种类无关。
• Fujikawa et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 1231,1233
  作者：Fujikawa et al.

  DOI：——

  日期：——
• SYNTHETIC TUBERCULOSTATS. II. AMINO- AND HYDROXY-PYRIDINE CARBOXYLIC ACID DERIVATIVES
  作者：H. HERBERT FOX

  DOI：10.1021/jo01138a006

  日期：1952.4
• The Synthesis of the Three Isomeric dl-β-Pyridylalanines
  作者：Carl Niemann、Richard N. Lewis、John T. Hays

  DOI：10.1021/ja01259a059

  日期：1942.7
• Pyridine compounds and method of manufacture
  申请人：HOFFMANN LA ROCHE

  公开号：US02676178A1

  公开（公告）日：1954-04-20