5-[(2,4-二氯苯基)亚甲基]-2-硫代-4-咪唑烷酮 | 6318-38-3

• 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
• 中文名称: 5-[(2,4-二氯苯基)亚甲基]-2-硫代-4-咪唑烷酮
• 英文名称: (5Z)-5-(2,4-dichlorobenzylidene)-2-thioxoimidazolidin-4-one
• 英文别名: (Z)-5-(2,4-dichlorobenzylidene)-2-thiohydantoin；5-(2,4-dichlorobenzylidene)-2-thiohydantoin；(5Z)-5-[(2,4-dichlorophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
• CAS: 6318-38-3
• 化学式: C₁₀H₆Cl₂N₂OS
• 分子量: 273.142
• InChiKey: XAMWGBWREMYZKV-BAQGIRSFSA-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：

  5-[(2,4-二氯苯基)亚甲基]-2-硫代-4-咪唑烷酮 以88%的产率得到
  参考文献：
  名称：

  SHALABY A. F. A.; DABOUN H. A.; ABDEL AZIZ M. A., Z. NATURFORSCH. , 1977, 32B, NO 8, 948-953

  摘要：

  DOI：
• 作为产物：
  描述：

  2-硫代乙内酰脲 、 2,4-二氯苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 0.08h， 以32%的产率得到5-[(2,4-二氯苯基)亚甲基]-2-硫代-4-咪唑烷酮
  参考文献：
  名称：

  特权支架或混杂粘合剂：罗丹宁及其相关杂环在药物化学中的比较研究

  摘要：

  罗丹宁和具有多个杂原子的相关五元杂环最近因在筛选活动中表现为“频繁的杀手”而成为非选择性化合物，因此在药物发现中几乎没有价值。但是，这种判断似乎主要是基于轶事证据。在筛选活动中鉴定出多种罗丹宁和相关化合物后，我们决定对它们的滥交进行系统的研究。合成了163种罗丹宁，乙内酰脲，硫代乙内酰脲和噻唑烷二酮，并针对几个目标进行了测试。还针对聚集和亲电反应性对化合物进行了表征，并分析了罗丹宁与相关化合物在已发表的X射线共晶结构中的结合模式。结果表明，环外，若丹宁和硫代乙内酰脲中的双键硫原子除具有其他结构特征外，还为极性相互作用和氢键提供了特别高的相互作用位点密度。这会导致“筛选范围”内浓度的混杂行为，但不应视为将此类筛选命中排除在进一步开发之外的一般剔除标准。建议将针对靶标亲和力和选择性的特殊标准应用于这些类型的化合物，并因此以有用的方式利用其特殊和潜在有价值的生物分子结合特性。这会导致“筛选范围”

  DOI：

  10.1021/jm201243p

文献信息

• Privileged Scaffolds or Promiscuous Binders: A Comparative Study on Rhodanines and Related Heterocycles in Medicinal Chemistry
  作者：Thomas Mendgen、Christian Steuer、Christian D. Klein

  DOI：10.1021/jm201243p

  日期：2012.1.26

  campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed

  罗丹宁和具有多个杂原子的相关五元杂环最近因在筛选活动中表现为“频繁的杀手”而成为非选择性化合物，因此在药物发现中几乎没有价值。但是，这种判断似乎主要是基于轶事证据。在筛选活动中鉴定出多种罗丹宁和相关化合物后，我们决定对它们的滥交进行系统的研究。合成了163种罗丹宁，乙内酰脲，硫代乙内酰脲和噻唑烷二酮，并针对几个目标进行了测试。还针对聚集和亲电反应性对化合物进行了表征，并分析了罗丹宁与相关化合物在已发表的X射线共晶结构中的结合模式。结果表明，环外，若丹宁和硫代乙内酰脲中的双键硫原子除具有其他结构特征外，还为极性相互作用和氢键提供了特别高的相互作用位点密度。这会导致“筛选范围”内浓度的混杂行为，但不应视为将此类筛选命中排除在进一步开发之外的一般剔除标准。建议将针对靶标亲和力和选择性的特殊标准应用于这些类型的化合物，并因此以有用的方式利用其特殊和潜在有价值的生物分子结合特性。这会导致“筛选范围”
• 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.
• Antimycobacterial activity of 5-arylidene aromatic derivatives of hydantoin
  作者：Ewa Szymańska、Katarzyna Kieć-Kononowicz

  DOI：10.1016/s0014-827x(01)01194-6

  日期：2002.4

  Various 5-(chlorobenzylidene)-2-isoniazido and 5-(chlorobenzylidene)-2-amino substituted derivatives of imidazoline-4-one were synthesized and evaluated in the primary assay for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv. Eight of them exhibited >90% inhibition in the primary screening at 12.5 mug/ml. For these primarily selected compounds the actual MIC and IC50 values were determined. Two of the isoniazid derivatives, for which MIC less than or equal to3.13 mug/ml and SI>10, were selected for further screening and investigated for efficacy in vitro in a TB-infected macrophage model. The most promising compound, 5-(3-chlorobenzylidene)-2-(isonicotinoylhydrazino)-imidazoline-4-one, with activity in vitro comparable with rifampin (MIC=0.8 mug/ml, SI>78) was tested in vivo in the animal tuberculosis model but exhibited insignificant activity. For several compounds the primary screening of antimycobacterial activity against Mycobacterium avium (ATCC 25291) was conducted as well, but none of them demonstrated satisfactory activity. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Bicyclic imidazole-4-one derivatives: a new class of antagonists for the orphan G protein-coupled receptors GPR18 and GPR55
  作者：V. Rempel、K. Atzler、A. Behrenswerth、T. Karcz、C. Schoeder、S. Hinz、M. Kaleta、D. Thimm、K. Kiec-Kononowicz、C. E. Müller

  DOI：10.1039/c3md00394a

  日期：——

  GPR18 and GPR55 are orphan G protein-coupled receptors (GPCRs) that interact with certain cannabinoid (CB) receptor ligands.

  GPR18和GPR55是孤儿G蛋白偶联受体（GPCRs），它们与特定的大麻素（CB）受体配体相互作用。
• SHALABY A. F. A.; DABOUN H. A.; ABDEL AZIZ M. A., Z. NATURFORSCH. <ZENA-AU>, 1977, 32B, NO 8, 948-953
  作者：SHALABY A. F. A.、 DABOUN H. A.、 ABDEL AZIZ M. A.

  DOI：——

  日期：——