1-acetyl-3-(2-methyl-4-nitrophenyl)thiourea

• 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: 1-acetyl-3-(2-methyl-4-nitrophenyl)thiourea
• 英文别名: N-[(2-methyl-4-nitrophenyl)carbamothioyl]acetamide
• 化学式: C₁₀H₁₁N₃O₃S
• 分子量: 253.282
• InChiKey: NBYLMUDDUIZFDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  potassium thioacyanate 、 乙酰氯 、 4-硝基-2-甲苯胺 以 水 、 丙酮 为溶剂， 反应 8.0h， 以92%的产率得到1-acetyl-3-(2-methyl-4-nitrophenyl)thiourea
  参考文献：
  名称：

  DNA-binding studies and biological activities of new nitrosubstituted acyl thioureas

  摘要：

  Four new nitrosubstituted acylthioureas i.e. 1-acetyl-3-(4-nitrophenyl)thiourea (TU1), 1-acety1-3-(2-methyl-4-nitrophenyl)thiourea (TU2), 1-acetyl-3-(2-methoxy-4-nitrophenyl)thiourea (TU3) and 1-acety1-3-(4-chloro-3-nitrophenyl)thiourea (TU4) have been synthesized and characterized (by C-13 and H-1 nuclear magnetic resonance, Fourier transform infrared spectroscopy and single crystal X-ray diffraction). As a preliminary investigation of the anti-cancer potencies of the said compounds, DNA interaction studies have been carried out using cyclic voltammetry and UV-vis spectroscopy along with verification from computational studies. The drug-DNA binding constants are found to be in the order, K-TU3 9.04 x 10(6) M-1 > K-TU4 8.57 x 10(6) M-1 > K-TU2 6.05 x 10(6) M-1 > K-TU1 1.16 x 10(6) M-1. Furthermore, the antioxidant, cytotoxic, antibacterial and antifungal activities have been carried out against DPPH (1,1-diphenyl-2-dipicrylhydrazyl), Brine shrimp eggs, gram positive (Micrococcus luteus, Staphylococcus aureus) and gram negative (Bordetella bronchiseptica, Salmonella typhimurium, Enterobacter aerogens) and fungal cultures (Aspergillus fumigatus, Mucor species, Aspergillus niger, Aspergillus flavus) respectively. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2015.06.024

文献信息

• DNA-binding studies and biological activities of new nitrosubstituted acyl thioureas
  作者：Shaista Tahir、Amin Badshah、Raja Azadar Hussain、Muhammad Nawaz Tahir、Saira Tabassum、Jahangir Ali Patujo、Muhammad Khawar Rauf

  DOI：10.1016/j.molstruc.2015.06.024

  日期：2015.11

  Four new nitrosubstituted acylthioureas i.e. 1-acetyl-3-(4-nitrophenyl)thiourea (TU1), 1-acety1-3-(2-methyl-4-nitrophenyl)thiourea (TU2), 1-acetyl-3-(2-methoxy-4-nitrophenyl)thiourea (TU3) and 1-acety1-3-(4-chloro-3-nitrophenyl)thiourea (TU4) have been synthesized and characterized (by C-13 and H-1 nuclear magnetic resonance, Fourier transform infrared spectroscopy and single crystal X-ray diffraction). As a preliminary investigation of the anti-cancer potencies of the said compounds, DNA interaction studies have been carried out using cyclic voltammetry and UV-vis spectroscopy along with verification from computational studies. The drug-DNA binding constants are found to be in the order, K-TU3 9.04 x 10(6) M-1 > K-TU4 8.57 x 10(6) M-1 > K-TU2 6.05 x 10(6) M-1 > K-TU1 1.16 x 10(6) M-1. Furthermore, the antioxidant, cytotoxic, antibacterial and antifungal activities have been carried out against DPPH (1,1-diphenyl-2-dipicrylhydrazyl), Brine shrimp eggs, gram positive (Micrococcus luteus, Staphylococcus aureus) and gram negative (Bordetella bronchiseptica, Salmonella typhimurium, Enterobacter aerogens) and fungal cultures (Aspergillus fumigatus, Mucor species, Aspergillus niger, Aspergillus flavus) respectively. (C) 2015 Elsevier B.V. All rights reserved.