2-thioxo-5-(2-chlorophenylmethylidene)-4-imidazolidinone | 215812-88-7

• 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: 2-thioxo-5-(2-chlorophenylmethylidene)-4-imidazolidinone
• 英文别名: 5-(2-chlorobenzylidene)-2-thiohydantoin；4-Imidazolidinone, 5-[(2-chlorophenyl)methylene]-2-thioxo-；(5Z)-5-[(2-chlorophenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
• CAS: 215812-88-7
• 化学式: C₁₀H₇ClN₂OS
• 分子量: 238.697
• InChiKey: HSAIZKCQBWCNNP-YVMONPNESA-N

物化性质

• 熔点：
  230-232 °C(Solv: ethanol (64-17-5))
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 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：

  2-thioxo-5-(2-chlorophenylmethylidene)-4-imidazolidinone 以82%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：

  3-(2-chlorophenyl)-2-isothiocyanatoacrylic acid ethyl ester 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以1.02 g的产率得到2-thioxo-5-(2-chlorophenylmethylidene)-4-imidazolidinone
  参考文献：
  名称：

  The Synthesis of 2-Alkylthio-3-alkyl-5-arylmethylidene4H-imidazol-4-ones

  摘要：

  2-alkylthio-3-alkyl-5-arylmethylidene-4H-imidazol-4-ones were synthesized by the S-alkylation and N-alkylation of 2-thioxo-5-arylmethylidene-4-imidazolidinones, which were obtained via a tandem aza-Wittig reaction of vinyliminophosphoranes, carbon disulfide, and excess ammonium hydroxide (28% NH3 in water).

  DOI：

  10.1080/10426500600614147

文献信息

• Imidazo[2,1-b]thiazepines: synthesis, structure and evaluation of benzodiazepine receptor binding
  作者：Katarzyna Kieć-Kononowicz、Janina Karolak-Wojciechowska、Barbara Michalak、Elżbieta Pękala、Britta Schumacher、Christa E Müller

  DOI：10.1016/j.ejmech.2003.11.009

  日期：2004.3

  of our search for new ligands acting on benzodiazepine receptors among the fused 2-thiohydantoin derivatives, a series of 5-substituted imidazo[2,1-b]thiazepines was synthesized and investigated in radioligand binding studies at the benzodiazepine binding site of GABA(A) receptors in rat brain cortical membranes. Among ortho-substituted 5-arylidene-imidazo[2,1-b]thiazepines compounds could be identified

  为了继续研究在稠合的2-硫代乙内酰脲衍生物中作用于苯并二氮杂receptor受体的新配体，合成了一系列5取代的咪唑并[2,1-b]硫氮杂s，并在放射性配体结合研究中对苯并二氮杂binding的结合位点进行了研究。大鼠脑皮质膜中的GABA（A）受体。在邻位取代的5-亚芳基-咪唑并[2，1-b]噻嗪类化合物中，可以鉴定出在低微摩尔浓度下对苯并二氮杂卓结合位点具有亲和力的化合物。已经对两种化合物（6ae和6ag）进行了X射线结构分析。为了分析构效关系，已经完成了所有化合物的3D模型（使用X射线数据）。检查了计算的理化性质（log P和log D）以及实验薄层色谱数据。
• 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。
• SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY OF SOME NEW N AND S-ALKYLATED ARYLIDENE-THIOXO-IMIDAZOLIDINONES
  作者：L.C. Santos、R.H.V. Mourão、F.T. Uchoa、T.G. Silva、D.J.N. Malta、R.O. Moura、M.C.A. Lima、S.L. Galdino、I.R. Pitta、J. Barbe

  DOI：10.1515/hc.2005.11.5.433

  日期：2005.1

  (2cyano-3-phenyl)-ethyl acrylates. Acrylates were prepared by refluxing equimolar mixture of aldehyde and ethyl cyanoacetate with piperidine in benzene, (if) Then compounds 2-9, were Ν alkylated at position 3 in the presence of potassium carbonate that leads to the imidazolidine potassium salt. Then, benzyl or phenyloxoethyl chlorides reacted in alcoholic medium [5] to yield the 3-benzyl-5-benzyli

  通过氰基丙烯酸酯的亲核加成，由取代的 2-thioxo-imidazolidin-4-one 制备了新的亚芳基-硫代-咪唑烷酮和 S-烷基化的亚芳基-咪唑烷酮衍生物。在碱性条件下用苄基或苯氧乙基氯化物处理 5-亚芳基-2-硫代-咪唑啉-4-酮，实现 Ν 和 S-烷基化。通过气袋试验和角叉菜胶诱导的爪水肿试验评价合成的咪唑烷的抗炎活性。引言 非甾体抗炎药 (NSAID) 广泛用于治疗炎症性疾病。使用非甾体抗炎药的主要限制在于它们的副作用，包括胃肠道溃疡和肾毒性。已知噻唑烷和生物等排咪唑烷具有抗炎活性，因为某些 5-亚芳基-4-硫代噻唑烷酮和 5-亚芳基-噻唑烷-2,4-二酮在 3 位被 4-氯苄基取代 [1]。一些 5-亚芳基-硫代咪唑烷酮和 3 位被苄基或苯氧乙基取代的硫代噻唑烷酮的合成，先前已报道[2-4]，新的 3-苄基-5-苄叉-2-硫代-的合成和理化数据imidazolidin-4-ones
• 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.
• Kiec-Kononowicz, Katarzyna; Karolak-Wojciechowska, Janina, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 73, # 1-4, p. 235 - 248
  作者：Kiec-Kononowicz, Katarzyna、Karolak-Wojciechowska, Janina

  DOI：——

  日期：——