(Z)-5-(2,6-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-(2,6-dichlorobenzylidene)-2-thiohydantoin
• 英文别名: 5-(2,6-dichlorobenzylidene)-2-thiohydantoin；(5Z)-5-[(2,6-dichlorophenyl)methylene]-2-thioxo-imidazolidin-4-one；(5Z)-5-[(2,6-dichlorophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
• 化学式: C₁₀H₆Cl₂N₂OS
• mdl: MFCD00642733
• 分子量: 273.142
• InChiKey: RNPXRLBHRIWCDV-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-(2,6-dichlorobenzylidene)-2-thiohydantoin 在 sodium ethanolate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 9.5h， 生成 5-(2,6-dichlorobenzylidene)-2-(isonicotinoylhydrazino)imidazoline-4-one
  参考文献：
  名称：

  Antimycobacterial activity of 5-arylidene aromatic derivatives of hydantoin

  摘要：

  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.

  DOI：

  10.1016/s0014-827x(01)01194-6
• 作为产物：
  描述：

  2-硫代乙内酰脲 、 2,6-二氯苯甲醛 生成 (Z)-5-(2,6-dichlorobenzylidene)-2-thiohydantoin
  参考文献：
  名称：

  Bicyclic imidazole-4-one derivatives: a new class of antagonists for the orphan G protein-coupled receptors GPR18 and GPR55

  摘要：

  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。

  DOI：

  10.1039/c3md00394a

文献信息

• Arylidene imidazothiazoles. Synthesis, structure and benzodiazepine receptor binding
  作者：Katarzyna Kieć-Kononowicz、Ewa Szymańska、Janina Karolak-Wojciechowska、Waldemar Ksiazek、Christa E. Müller、Uli Geis

  DOI：10.1002/jhet.5570360139

  日期：1999.1

  A series of arylidene imidazo[2,1-b]thiazoles was synthesized, in order to investigate the influence of different spatial arrangements of the arylidene substituent towards the bicyclic structure of imidazo[2,1-b]-thiazole on benzodiazepine receptor affinity. 1,2- And 2,3-cyclized derivatives of mono- and di-substituted Z-5-arylidene-2-thiohydantoins were investigated. As an example of E isomers E-5-benzylidene-2

  一系列亚芳咪唑并[2,1- b ]噻唑的合成，为了研究的亚芳基的取代基的空间排列不同朝向咪唑并[2,1-的双环结构的影响b〕噻唑于苯并二氮杂受体的亲和力。1,2-和2,3-环化的衍生物的单-和二-取代的Z-5-亚芳基-2- thiohydantoins进行了调查。作为一个例子ë异构体Ë -5-亚苄基-2,3-二氢咪唑并[2,1- b ]噻唑-6（5 ħ）-获得了一个。亚芳基取代基朝向双环结构的空间排列以及异构体的特性对化合物的苯并二氮杂receptor受体亲和力影响很小。似乎对生物活性的最大影响是苯环上取代基的性质和数量。所有研究的咪唑并[2,1- b ]噻唑较先前所描述的亚芳基咪唑并[2,1-活性较低b ] thiazepinones。
• 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.
• Geis, Uli; Kiec-Kononowicz, Katarzyna; Mueller, Christa E., Scientia Pharmaceutica, 1996, vol. 64, # 3-4, p. 383 - 390
  作者：Geis, Uli、Kiec-Kononowicz, Katarzyna、Mueller, Christa E.

  DOI：——

  日期：——
• 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。
• 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.