1-(4-chlorophenyl)-4-imino-3-(4-methoxyphenyl)-5-thioxoimidazolidin-2-one | 1310368-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-(4-chlorophenyl)-4-imino-3-(4-methoxyphenyl)-5-thioxoimidazolidin-2-one
• 英文别名: 1-(4-Chlorophenyl)-4-imino-3-(4-methoxyphenyl)-5-thioxo-imidazolidin-2-one；1-(4-chlorophenyl)-4-imino-3-(4-methoxyphenyl)-5-sulfanylideneimidazolidin-2-one
• CAS: 1310368-81-0
• 化学式: C₁₆H₁₂ClN₃O₂S
• 分子量: 345.809
• InChiKey: GUUSCZWLIBLPRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  88.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-氯苯基)-1-氰基硫代甲酰胺 、 对甲氧基苯异氰酸酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 1-(4-chlorophenyl)-4-imino-3-(4-methoxyphenyl)-5-thioxoimidazolidin-2-one
  参考文献：
  名称：

  Synthesis and characterization of new types of halogenated and alkylated imidazolidineiminothiones and a comparative study of their antitumor, antibacterial, and antifungal activities

  摘要：

  A series of twenty novel imidazolidineiminothiones (4-8) with various substituents at N-(1) and N-(3) were synthesized by various permutations of halogenated and alkylated N-arylcyanothioformanilides (1) with aromatic isocyanates (2). Preliminary screening of all compounds against Ehrlich ascites carcinoma cells (EAC) indicated that 5d, and 8a c were the most active compounds as they displayed the highest percent inhibition of cell viability (80%, 70%, 80%, and 70%, respectively). Thus, they were further subjected to in vitro biological evaluation against other tumor cancer cell lines (HEPG2, HEP2, MCF7, HELA, and HCT116). The IC50 values ranged from 3.12 to 12.1 mu g/mL where compound 8b (N-(1): 2,4-dimethoxyphenyl: N-(3): 4-methoxyphenyl) was markedly active against all cell lines and consistently produced low IC50 values in all cases (ranging from 3.12 to 4.34 mu g/mL). This underscored the synergistic effect of the suitably positioned methoxy groups on the aromatic rings of N-(1) and N-(3) of the imidazolidineiminothiones. All compounds were also tested against microbial organisms (Escherichia coli, Sarcina lutea, Bacillus subtilis, and Staphylococcus aureus), and fungal strains (Candida albicans and Aspergillus flavus). Most tested compounds showed significant activities which could be optimized with the appropriate selection of matching aromatic substituents on N-(1) and N-(3). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.009

文献信息

• Synthesis and characterization of new types of halogenated and alkylated imidazolidineiminothiones and a comparative study of their antitumor, antibacterial, and antifungal activities
  作者：Ziad Moussa、Marwa A.M.Sh. El-Sharief、Ahmed M.Sh. El-Sharief

  DOI：10.1016/j.ejmech.2011.03.009

  日期：2011.6

  A series of twenty novel imidazolidineiminothiones (4-8) with various substituents at N-(1) and N-(3) were synthesized by various permutations of halogenated and alkylated N-arylcyanothioformanilides (1) with aromatic isocyanates (2). Preliminary screening of all compounds against Ehrlich ascites carcinoma cells (EAC) indicated that 5d, and 8a c were the most active compounds as they displayed the highest percent inhibition of cell viability (80%, 70%, 80%, and 70%, respectively). Thus, they were further subjected to in vitro biological evaluation against other tumor cancer cell lines (HEPG2, HEP2, MCF7, HELA, and HCT116). The IC50 values ranged from 3.12 to 12.1 mu g/mL where compound 8b (N-(1): 2,4-dimethoxyphenyl: N-(3): 4-methoxyphenyl) was markedly active against all cell lines and consistently produced low IC50 values in all cases (ranging from 3.12 to 4.34 mu g/mL). This underscored the synergistic effect of the suitably positioned methoxy groups on the aromatic rings of N-(1) and N-(3) of the imidazolidineiminothiones. All compounds were also tested against microbial organisms (Escherichia coli, Sarcina lutea, Bacillus subtilis, and Staphylococcus aureus), and fungal strains (Candida albicans and Aspergillus flavus). Most tested compounds showed significant activities which could be optimized with the appropriate selection of matching aromatic substituents on N-(1) and N-(3). (C) 2011 Elsevier Masson SAS. All rights reserved.