N-(2-(hydrazinecarbonyl)phenyl)thiophene-2-carboxamide

• 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-(2-(hydrazinecarbonyl)phenyl)thiophene-2-carboxamide
• 英文别名: N-[2-(hydrazinecarbonyl)phenyl]thiophene-2-carboxamide
• 化学式: C₁₂H₁₁N₃O₂S
• 分子量: 261.304
• InChiKey: HPKUGSVZBXJAKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-(hydrazinecarbonyl)phenyl)thiophene-2-carboxamide 在 氢氧化钾 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-[3-(2-Amino-phenyl)-5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl]-2-methoxy-3H-quinazolin-4-one
  参考文献：
  名称：

  Abdel-Hamid, Hoda A.; Shiba, Sayed A.; El-Khamry, Abdel-Momen A., Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 72, # 1.4, p. 237 - 248

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(2-methoxycarbonylphenyl)thiophene-2-carboxamide 在 肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-(2-(hydrazinecarbonyl)phenyl)thiophene-2-carboxamide
  参考文献：
  名称：

  苯甲酰肼的噻吩-2-甲酰胺席夫碱衍生物作为新型乙酰胆碱酯酶和丁酰胆碱酯酶抑制剂的设计、合成、构效关系和分子对接研究

  摘要：

  通过体外分析，设计、合成、表征和探索了噻吩-2-甲酰胺基苯甲酰肼的新型腙衍生物作为胆碱酯酶抑制剂和抗氧化剂的潜力。通过与 2-噻吩羰基氯反应，将邻氨基苯甲酸甲酯 (1) 衍生为 2-(噻吩-2-甲酰胺基)苯甲酸甲酯 (3)。化合物3进一步用水合肼处理得到N-(2-(肼羰基)苯基)噻吩-2-甲酰胺(4)。4 与各种醛进一步反应，以良好的收率（> 85％）获得所需的席夫碱衍生物（5-20​​）。所有化合物 (1-20) 均通过 FTIR、NMR 光谱和质谱分析进行表征。生物学评价结果清楚地表明，大多数合成的化合物 (5-20) 是有效的双重抑制剂，对丁酰胆碱酯酶 (BChE) 和乙酰胆碱酯酶 (AChE) 酶的抑制值不同。值得注意的是，相对于标准多奈哌齐（BChE 的抑制百分比 = 92.34% 和 95.24%），化合物 13 被确定为该系列中 BChE（抑制百分比 = 90.16%）和 AChE（抑制百分比

  DOI：

  10.1016/j.molstruc.2021.130983

文献信息

• Design, synthesis, structure activity relationship and molecular docking studies of thiophene-2-carboxamide Schiff base derivatives of benzohydrazide as novel acetylcholinesterase and butyrylcholinesterase inhibitors
  作者：Naghmana Kausar、Shahzad Murtaza、Muhammad Nadeem Arshad、Rubina Munir、Rahman Shah Zaib Saleem、Hummera Rafique、Abdul Tawab

  DOI：10.1016/j.molstruc.2021.130983

  日期：2021.11

  characterized by using FTIR, NMR spectroscopies and Mass spectrometric analysis. The biological evaluation results clearly showed that most of the synthesized compounds (5–20) are effective dual inhibitors with varying% inhibition values against butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzymes. Remarkably, compound 13 was established as the most active inhibitor of both BChE (% inhibition = 90

  通过体外分析，设计、合成、表征和探索了噻吩-2-甲酰胺基苯甲酰肼的新型腙衍生物作为胆碱酯酶抑制剂和抗氧化剂的潜力。通过与 2-噻吩羰基氯反应，将邻氨基苯甲酸甲酯 (1) 衍生为 2-(噻吩-2-甲酰胺基)苯甲酸甲酯 (3)。化合物3进一步用水合肼处理得到N-(2-(肼羰基)苯基)噻吩-2-甲酰胺(4)。4 与各种醛进一步反应，以良好的收率（> 85％）获得所需的席夫碱衍生物（5-20​​）。所有化合物 (1-20) 均通过 FTIR、NMR 光谱和质谱分析进行表征。生物学评价结果清楚地表明，大多数合成的化合物 (5-20) 是有效的双重抑制剂，对丁酰胆碱酯酶 (BChE) 和乙酰胆碱酯酶 (AChE) 酶的抑制值不同。值得注意的是，相对于标准多奈哌齐（BChE 的抑制百分比 = 92.34% 和 95.24%），化合物 13 被确定为该系列中 BChE（抑制百分比 = 90.16%）和 AChE（抑制百分比
• New Anthranilic Acid Hydrazones as Fenamate Isosteres: Synthesis, Characterization, Molecular Docking, Dynamics &amp; <i>in Silico</i> ADME, <i>in Vitro</i> Anti‐Inflammatory and Anticancer Activity Studies
  作者：Halil Şenol、Zeynep Çağman、Tuğba Gençoğlu Katmerlikaya、Feyzi Sinan Tokalı

  DOI：10.1002/cbdv.202300773

  日期：2023.8

  In this study, twenty new anthranilic acid hydrazones 6–9 (a–e) were synthesized and their structures were characterized by Fourier-transform Infrared (FT-IR), Nuclear Magnetic Resonance (1H-NMR – 13C-NMR), and High-resolution Mass Spectroscopy (HR-MS). The inhibitory effects of the compounds against COX-II were evaluated. IC50 values of the compounds were found in the range of >200–0.32 μM and compounds

  在这项研究中，合成了20种新的邻氨基苯甲酸腙6 – 9 ( a – e )，并通过傅里叶变换红外(FT-IR)、核磁共振( 1 H-NMR – 13 C-NMR)表征了它们的结构，和高分辨率质谱（HR-MS）。评价了化合物对COX-II的抑制作用。化合物的IC 50值在 >200–0.32 μM 范围内，化合物6e、8d、8e、9b、9c和9e被确定为最有效的抑制剂。研究了最有效的化合物对人肝母细胞瘤 (Hep-G2) 和人健康胚胎肾 (Hek-293) 细胞系的细胞毒性作用。使用阿霉素（IC 50：Hep-G2 为 8.68±0.16 μM，Hek-293 为 55.29±0.56 μM）作为标准品。8e是最活跃的化合物，对 Hep-G2 的IC 50较低 (4.80±0.04 μM)，对 Hek-293 的 IC 50 较高 (159.30±3.12)，且选择性较高 (33.15)。最
• Synthesis, characterization, biological evaluation and molecular docking studies of N-functionalized derivatives of 2-aminobenzohydrazide
  作者：Naghmana Kausar、Shahzad Murtaza、Muhammad Nadeem Arshad、Robina Rashid、Abdullah M. Asiri、Noman Javid、Mulazim Hussain Asim、Zaman Ashraf

  DOI：10.1016/j.molstruc.2020.128042

  日期：2020.6

  In this paper, N-functionalized derivatives of methyl anthranilate (1-3) were prepared by reacting it with various acid chlorides to give amide derivatives (1-3) which were further converted to benzohydrazide derivatives (4-6) by reacting them with hydrazine. These N-functionalized derivatives of 2-aminobenzohydrazide (4-6) were reacted with 4-triflouromethyl benzaldehyde to give schiff base derivatives (7-9). All the synthesized compounds (1-9) were characterized by Mass spectrometry as well as NMR and FTIR spectroscopic techniques. Single Crystal X-ray diffraction analysis technique (XRD) was utilized to analyze crystalline compound 1. AChE and BChE enzymes inhibition potential was checked for the synthesized compounds. Putative binding approaches of screened compounds were explored by molecular docking studies. Synthesized compounds were also checked for antioxidant activity. Enzyme inhibition analysis showed that compounds 2 and 9 exhibited good AChE inhibition showing 68% and 60% percentage inhibition, respectively, while very good BChE inhibition activities were shown by compounds 2 (70%) and 5 (76%). Enzyme inhibition results were also supported by molecular docking studies with lowest binding energy values of -9.79 kcal mol(-1) for BChE and -9.55 kcal mol(-1) for AChE for compound 9. Hydrazide derivatives (4-6) showed very significant results for antioxidant activity with percentage scavenging greater than 90%. (C) 2020 Elsevier B.V. All rights reserved.
• EL-KHAMRY, ABDEL MOMEN A.;EL-NAGDY, S.;SHABAN, M. E., EGYPT. J. CHEM., 31,(1988) N, C. 241-249
  作者：EL-KHAMRY, ABDEL MOMEN A.、EL-NAGDY, S.、SHABAN, M. E.

  DOI：——

  日期：——
• EL-KHAMRY, ABDEL MOMEN A.;EL-NAGDY, S.;SHABAN, M. E., REV. ROUM. CHIM., 33,(1988) N 8, C. 833-838
  作者：EL-KHAMRY, ABDEL MOMEN A.、EL-NAGDY, S.、SHABAN, M. E.

  DOI：——

  日期：——