2-(1H-benzo[d]imidazole-2-ylthio)-N-(2-nitrophenyl)acetamide | 356776-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(1H-benzo[d]imidazole-2-ylthio)-N-(2-nitrophenyl)acetamide
• 英文别名: 2-(1H-benzimidazol-2-ylsulfanyl)-N-(2-nitrophenyl)acetamide
• CAS: 356776-28-8
• 化学式: C₁₅H₁₂N₄O₃S
• mdl: MFCD01423766
• 分子量: 328.351
• InChiKey: FMYUHAKWLSNXNQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1H-benzo[d]imidazole-2-ylthio)-N-(2-nitrophenyl)acetamide 在 吡啶 、 乙酸酐 作用下， 反应 2.0h， 以80%的产率得到Benzo[4,5]imidazo[2,1-b]thiazol-3-yl-(2-nitro-phenyl)-amine
  参考文献：
  名称：

  El Sherief; Mahmoud; Abdel Rahman, Journal of the Indian Chemical Society, 1983, vol. 60, # 1, p. 58 - 60

  摘要：

  DOI：
• 作为产物：
  描述：

  1H-苯并咪唑-2-硫醇 在 alkaline medium 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2-(1H-benzo[d]imidazole-2-ylthio)-N-(2-nitrophenyl)acetamide
  参考文献：
  名称：

  El Sherief; Mahmoud; Abdel Rahman, Journal of the Indian Chemical Society, 1983, vol. 60, # 1, p. 58 - 60

  摘要：

  DOI：

文献信息

• Design, synthesis, and biological activity studies on benzimidazole derivatives targeting myeloperoxidase
  作者：Merve Saylam、Fadime Aydın Köse、Aysun Pabuccuoglu、Duygu Barut Celepci、Muhittin Aygün、Varol Pabuccuoglu

  DOI：10.1016/j.ejmech.2022.115083

  日期：2023.2

  injury, multiple sclerosis, cardiovascular and neurodegenerative diseases. Therefore, the enzyme currently draws attention as a potential therapeutic target. In this study, isomeric 1,3-dihydro-2H-benzo[d]imidazole-2-thione derivatives having amide, hydrazide and hydroxamic acid groups either on nitrogen or on sulphur atom were designed and their inhibitory activity was determined on chlorination and peroxidation

  髓过氧化物酶 (MPO) 通过产生的次氯酸 (HOCl) 氧化吞噬溶酶体中微生物的重要分子，从而在人体抗菌系统中发挥关键作用。然而，MPO 可以释放到吞噬细胞外并产生反应性中间体，导致组织损伤。MPO 作为组织损伤的局部介质，与肾损伤、多发性硬化、心血管和神经退行性疾病等炎症性疾病有关。因此，该酶目前作为潜在的治疗靶点而备受关注。在这项研究中，同分异构的 1,3-dihydro-2 H -benzo[ d设计了在氮原子或硫原子上具有酰胺、酰肼和异羟肟酸基团的咪唑-2-硫酮衍生物，并测定了它们对 MPO 的氯化和过氧化循环的抑制活性。在这些化合物中，2-(2-thioxo-2,3-dihydro-1H-benzo[d]imidazole -1-yl )acetohydrazide (C19)被发现是两个循环中最活跃的抑制剂。
• Spectroscopic behavior, FMO, NLO and substitution effect of 2-(1H-Benzo[d]imidazole-2-ylthio)-N-o-substituted-acetamides: Experimental and theoretical approach
  作者：Ali Muhammad Arif、Afifa Yousaf、Hong-liang Xu、Zhong-Min Su

  DOI：10.1016/j.dyepig.2019.107742

  日期：2019.12

  The benzimidazole-based derivatives 2a-c were designed and synthesized via C-N coupling reaction and experimentally characterized by infrared spectroscopy (FT-IR), nuclear magnetic resonance (H-1 NMR) spectroscopy and mass spectrometry (MS). The observed and calculated FT-IR frequencies correspond to C=O stretching of amide group are depicted at 1657, 1672 and 1682, 1689 and 1699, 1682 for 2a, 2b and 2c respectively and are in good agreement. The synthesized compounds 2a-c exhibit non-linear optical response with the first hyperpolarizability (beta(0)) at 783, 1550 and 694 au, respectively. Due to the presence of electron withdrawing -NO2 on the primary amine of 2b, the beta(0) value is estimated at 1550 au, which reduces the energy barrier hence increasing the beta(0) value, with maximum UV-vis absorption at 224 nm with TD-DFT method. The opposite behavior is demonstrated by the electron donor -OCH3 substituent. This study of NLO responses would be beneficial to the development of high-performance NLO materials.
• El Sherief; Mahmoud; Abdel Rahman, Journal of the Indian Chemical Society, 1983, vol. 60, # 1, p. 58 - 60
  作者：El Sherief、Mahmoud、Abdel Rahman、El Naggar

  DOI：——

  日期：——