(Z)-5-(3,4-dichlorobenzylidene)-2-thiohydantoin

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-5-(3,4-dichlorobenzylidene)-2-thiohydantoin
• 英文别名: (5Z)-5-[(3,4-dichlorophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
• 化学式: C₁₀H₆Cl₂N₂OS
• 分子量: 273.142
• InChiKey: SZLGETBWNTYETJ-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-(3,4-dichlorobenzylidene)-2-thiohydantoin 、 碘甲烷 在 乙醇 、 sodium 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity

  摘要：

  Series of novel 5-arylidene-2-arylaminothiazol-4(5H)-ones and 2-aryl(benzyl)amino-1H-imidazol-4(5H)ones were synthesized from appropriate 2-alkylthioazol-4-ones using nucleophilic substitution in position 2 by various anilines and benzylamines and Knoevenagel reaction. X-ray structural studies of 22 revealed the structure to be intermediate between amino and imino tautomeric forms. All the target compounds were evaluated for the anticancer activity in vitro in standard National Cancer Institute 60 cancer cell lines assay. Majority of compounds showed significant antitumor cytotoxicity effect at micromolar and submicromolar level (Mean Log GI(50) ranges -5.77 to -4.35). Some of the most potent compounds, namely 10 and 13, possessed selectively high effect on all leukemia cell lines at submicromolar level (Mean Log GI50 [leukemia lines], respectively, -6.41 and -6.29), which are probably associated with immunosuppressive activity. Individual cancer cell lines sensitivity to synthesized compounds and SAR studies are discussed. COMPARE analysis allowed to disclose probable modes of anticancer action for synthesized compounds, in particular showed number of high correlations with activity patterns of alkylating agents (PCC similar to 0.606-0.731). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.073
• 作为产物：
  描述：

  2-硫代乙内酰脲 、 3,4-二氯苯甲醛 在 sodium acetate 、 溶剂黄146 作用下， 反应 2.0h， 以78%的产率得到(Z)-5-(3,4-dichlorobenzylidene)-2-thiohydantoin
  参考文献：
  名称：

  Antimycobacterial activity of 5-arylidene derivatives of hydantoin

  摘要：

  The synthesis of various 5-arylidene-2-thiohydantoins and results of the primary assay in vitro for their antimycobacterial activity is reported. Eight of those compounds exhibited > 90% inhibition of Mycobacterium tuberculosis growth and for them the minimum inhibitory concentrations, cytotoxicity (IC50) and the selectivity index values were determined. The most active structure, (5Z)-5(1,1'-biphenyl-4-ylmethylene)-2-thioxoimidazolidin-4-one, showed MIC = 0.78 mug/ml. For all compounds log P and log D (pH 6.5) values were calculated. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0014-827x(02)01292-2

文献信息

• Antimycobacterial activity of 5-arylidene derivatives of hydantoin
  作者：K Kieć-Kononowicz、E Szymańska

  DOI：10.1016/s0014-827x(02)01292-2

  日期：2002.11

  The synthesis of various 5-arylidene-2-thiohydantoins and results of the primary assay in vitro for their antimycobacterial activity is reported. Eight of those compounds exhibited > 90% inhibition of Mycobacterium tuberculosis growth and for them the minimum inhibitory concentrations, cytotoxicity (IC50) and the selectivity index values were determined. The most active structure, (5Z)-5(1,1'-biphenyl-4-ylmethylene)-2-thioxoimidazolidin-4-one, showed MIC = 0.78 mug/ml. For all compounds log P and log D (pH 6.5) values were calculated. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.
• Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity
  作者：Ivanna Subtel’na、Dmytro Atamanyuk、Ewa Szymańska、Katarzyna Kieć-Kononowicz、Borys Zimenkovsky、Olexandr Vasylenko、Andrzej Gzella、Roman Lesyk

  DOI：10.1016/j.bmc.2010.05.073

  日期：2010.7

  Series of novel 5-arylidene-2-arylaminothiazol-4(5H)-ones and 2-aryl(benzyl)amino-1H-imidazol-4(5H)ones were synthesized from appropriate 2-alkylthioazol-4-ones using nucleophilic substitution in position 2 by various anilines and benzylamines and Knoevenagel reaction. X-ray structural studies of 22 revealed the structure to be intermediate between amino and imino tautomeric forms. All the target compounds were evaluated for the anticancer activity in vitro in standard National Cancer Institute 60 cancer cell lines assay. Majority of compounds showed significant antitumor cytotoxicity effect at micromolar and submicromolar level (Mean Log GI(50) ranges -5.77 to -4.35). Some of the most potent compounds, namely 10 and 13, possessed selectively high effect on all leukemia cell lines at submicromolar level (Mean Log GI50 [leukemia lines], respectively, -6.41 and -6.29), which are probably associated with immunosuppressive activity. Individual cancer cell lines sensitivity to synthesized compounds and SAR studies are discussed. COMPARE analysis allowed to disclose probable modes of anticancer action for synthesized compounds, in particular showed number of high correlations with activity patterns of alkylating agents (PCC similar to 0.606-0.731). (C) 2010 Elsevier Ltd. All rights reserved.