5-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-2-methylsulfanyl-3,5-dihydro-imidazol-4-one | 215812-89-8

• 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: 5-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-2-methylsulfanyl-3,5-dihydro-imidazol-4-one
• 英文别名: (4Z)-4-[(2-chlorophenyl)methylidene]-2-(methylsulfanyl)-4,5-dihydro-1H-imidazol-5-one；(4Z)-4-[(2-chlorophenyl)methylidene]-2-methylsulfanyl-1H-imidazol-5-one
• CAS: 215812-89-8
• 化学式: C₁₁H₉ClN₂OS
• 分子量: 252.724
• InChiKey: DRKJMQABKNJFFQ-TWGQIWQCSA-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-2-methylsulfanyl-3,5-dihydro-imidazol-4-one 在 potassium tert-butylate 作用下， 以 吡啶 、 乙醇 为溶剂， 生成 2-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-6,7,8,9-tetrahydro-2H-imidazo[1,2-a][1,3]diazepine-3,5-dione
  参考文献：
  名称：

  咪唑并噻嗪，-二氮酮和-二氮杂酮衍生物。合成，结构与苯并二氮杂receptor受体结合。

  摘要：

  在我们寻找对稠合的2-硫代乙内酰脲衍生物中的苯并二氮杂receptor受体起作用的新化合物的过程中，合成了一系列的亚芳基咪唑并[2,1-b]噻嗪。检查了单取代和二取代的Z-5-芳基-2-硫代乙内酰脲的1,2-和2,3-环化衍生物（Z-2-肉桂亚基-6,7-二氢-测定5H-咪唑并[2，1-b] [1，3]噻嗪-3（2H）-1），并与二苯基衍生物进行比较。为了研究退火环类型对生物活性的影响，获得了咪唑并[2,1-b]嘧啶酮和咪唑并[2,1-b]二氮杂酮衍生物。用于脱核的方法（1,2-和2,3-环化异构体，但稠合的亚芳基咪唑并噻嗪除外），取代方式（亚芳基对二苯基）以及退火环的特性对所研究化合物的苯并二氮杂receptor受体亲和力影响较小。似乎对生物活性的最大影响在于亚芳基环上取代基的特征和位置。

  DOI：

  10.1016/s0223-5234(01)01239-9
• 作为产物：
  描述：

  2-thioxo-5-(2-chlorophenylmethylidene)-4-imidazolidinone 、 碘甲烷 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 5-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-2-methylsulfanyl-3,5-dihydro-imidazol-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

文献信息

• 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.
• DABOUN H. A.; ABD-ELFATTAH A. M.; HUSSEIN M. M.; SHALABY A. F. A., Z. NATURFORSCH., 1981, B 36, NO 3, 366-369
  作者：DABOUN H. A.、 ABD-ELFATTAH A. M.、 HUSSEIN M. M.、 SHALABY A. F. A.

  DOI：——

  日期：——
• Imidazo-thiazine, -diazinone and -diazepinone derivatives. Synthesis, structure and benzodiazepine receptor binding
  作者：Katarzyna Kieć-Kononowicz、Janina Karolak-Wojciechowska、Christa E. Müller、Britta Schumacher、Elżbieta Pękala、Ewa Szymańska

  DOI：10.1016/s0223-5234(01)01239-9

  日期：2001.5

  biological activity, imidazo[2,1-b]pyrimidinone and imidazo[2,1-b]diazepinone derivatives were obtained. The method used in annelation (1,2- and 2,3-cyclized isomers with the exception of fused arylidene imidazothiazines), the substitution pattern (arylidene towards diphenyl) as well as the character of the annelated ring had minor influence on the benzodiazepine receptor affinity of the investigated

  在我们寻找对稠合的2-硫代乙内酰脲衍生物中的苯并二氮杂receptor受体起作用的新化合物的过程中，合成了一系列的亚芳基咪唑并[2,1-b]噻嗪。检查了单取代和二取代的Z-5-芳基-2-硫代乙内酰脲的1,2-和2,3-环化衍生物（Z-2-肉桂亚基-6,7-二氢-测定5H-咪唑并[2，1-b] [1，3]噻嗪-3（2H）-1），并与二苯基衍生物进行比较。为了研究退火环类型对生物活性的影响，获得了咪唑并[2,1-b]嘧啶酮和咪唑并[2,1-b]二氮杂酮衍生物。用于脱核的方法（1,2-和2,3-环化异构体，但稠合的亚芳基咪唑并噻嗪除外），取代方式（亚芳基对二苯基）以及退火环的特性对所研究化合物的苯并二氮杂receptor受体亲和力影响较小。似乎对生物活性的最大影响在于亚芳基环上取代基的特征和位置。
• 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.