(4Z)-4-[(furan-2-yl)methylene]-2-(methylthio)-1H-imidazol-5(4H)-one | 91122-00-8

• 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: (4Z)-4-[(furan-2-yl)methylene]-2-(methylthio)-1H-imidazol-5(4H)-one
• 英文别名: 5-furfurylidene-2-methylsulfanyl-3,5-dihydro-imidazol-4-one；5-Furfuryliden-2-methylmercapto-3,5-dihydro-imidazol-4-on；(4Z)-4-(furan-2-ylmethylidene)-2-methylsulfanyl-1H-imidazol-5-one
• CAS: 91122-00-8
• 化学式: C₉H₈N₂O₂S
• 分子量: 208.241
• InChiKey: ZRGUIERVLVHPCB-ALCCZGGFSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4Z)-4-[(furan-2-yl)methylene]-2-(methylthio)-1H-imidazol-5(4H)-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以25%的产率得到5-[1-Furan-2-yl-meth-(Z)-ylidene]-2-hydrazono-imidazolidin-4-one
  参考文献：
  名称：

  方便地制备 2-(2-Arylidene)- 和 2-(2-Polyhydroxyalkylidene)hydrazono-4-imidazolidinones，在 5 位具有各种杂环侧链取代基作为潜在的抗病毒和抗肿瘤剂

  摘要：

  多种新型5-[(Z)-亚芳基]-2-[(2-(E)-亚芳基)腙]-4-咪唑烷酮1a-c至4a、b和5-[(Z)-亚芳基]- 2-[(2-( E )-聚羟基亚烷基) 腙]-4-咪唑烷酮 5a-c 至 7a-c 由 5-[( Z )-亚芳基]-2-甲基巯基乙内酰脲 8a-c 与 2- (E)-亚芳基腙13a-d和/或2-(E)-单糖腙16a-c。产品选择了线性结构，而不是有角异构体的结构。该结构已从 5-[(Z)-2-thienylidene]-2-hydrazono-4-imidazolidinone 9a 分别与苯甲醛和 D-半乳糖缩合的模型研究中得到证实。已经研究了化合物 1-7 的乙酰化和苯甲酰化反应。测试了所有新化合物的潜在抗病毒和抗肿瘤活性。

  DOI：

  10.1080/10426500211714
• 作为产物：
  描述：

  4-furfurylidene-2-thioxo-thiazolidin-5-one 在 氢氧化钾 、 ammonium hydroxide 作用下， 生成 (4Z)-4-[(furan-2-yl)methylene]-2-(methylthio)-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  Cook et al., Journal of the Chemical Society, 1950, p. 1892,1896

  摘要：

  DOI：

文献信息

• SYNTHESIS, CONFORMATIONAL ANALYSIS AND ANTITUMOR TESTING OF 5-(<i>Z</i>)-ARYLIDENE-4-IMIDAZOLIDINONE DERIVATIVES
  作者：A. I. Khodair、H. I. El-subbagh、A. M. Al-obaid

  DOI：10.1080/10426509808035741

  日期：1998.9.1

  5-(Z)-arylidene-3-aminomethyl-2-thioxo-4-imidazolidinones 42–55 and 5-(Z)-arylidene-3-aminomethyl-2-methylmercapto-4-imidazolidinones 56–67 have been synthesized via two different routes. Conformational analysis and antitumor activities have been studied. The antitumor activity of these compounds showed broad spectrum of activity against a wide range of different human cell lines of nine tumor subpanels

  摘要 一系列 5-(Z)-arylidene-2-amino-4-imidazolidinones 16–34, 5-(Z)-arylidene-2-(2-carboxyphenylamino)-4-imidazolidinones 35–41, 5-(Z) )-arylidene-3-aminomethyl-2-thioxo-4-imidazolidinones 42–55 和 5-(Z)-arylidene-3-aminomethyl-2-methylmercapto-4-imidazolidinones 56–67 已通过两种不同的途径合成。已经研究了构象分析和抗肿瘤活性。这些化合物的抗肿瘤活性显示出对九个肿瘤亚组的多种不同人类细胞系的广谱活性，导致细胞抑制和细胞毒性效力。
• A Convenient Preparation of 2-(2-Arylidene)- and 2-(2-Polyhydroxyalkylidene)hydrazono-4-imidazolidinones with Various Heterocyclic Side Chain Substituents at Position 5 as Potential Antiviral and Antitumor Agents
  作者：Ahmed I. Khodair

  DOI：10.1080/10426500211714

  日期：2002.5.1

  A variety of novel 5-[( Z )-arylidene]-2-[(2-( E )-arylidene)hydrazono]-4-imidazolidinones 1a-c to 4a , b and 5-[( Z )-arylidene]-2-[(2-( E )-polyhydroxyalkylidene)hydrazono]-4-imidazolidinones 5a-c to 7a-c were prepared from the reaction of 5-[( Z )-arylidene]-2-methylmercaptohydantoins 8a-c with 2-( E )-arylidene hydrazones 13a-d and/or 2-( E )-monosaccharides hydrazones 16a-c . The linear structure

  多种新型5-[(Z)-亚芳基]-2-[(2-(E)-亚芳基)腙]-4-咪唑烷酮1a-c至4a、b和5-[(Z)-亚芳基]- 2-[(2-( E )-聚羟基亚烷基) 腙]-4-咪唑烷酮 5a-c 至 7a-c 由 5-[( Z )-亚芳基]-2-甲基巯基乙内酰脲 8a-c 与 2- (E)-亚芳基腙13a-d和/或2-(E)-单糖腙16a-c。产品选择了线性结构，而不是有角异构体的结构。该结构已从 5-[(Z)-2-thienylidene]-2-hydrazono-4-imidazolidinone 9a 分别与苯甲醛和 D-半乳糖缩合的模型研究中得到证实。已经研究了化合物 1-7 的乙酰化和苯甲酰化反应。测试了所有新化合物的潜在抗病毒和抗肿瘤活性。
• [EN] AROMATIC IMIDAZOLIDINONE DERIVATIVES AND THEIR USE IN THE TREATMENT OF DISEASES OF BACTERIAL NATURE<br/>[FR] DÉRIVÉS D'IMIDAZOLIDINONES AROMATIQUES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES DE NATURE BACTÉRIENNE
  申请人：UNIV JAGIELLONSKI

  公开号：WO2013151450A1

  公开（公告）日：2013-10-10

  The invention introduces new derivatives of aromatic imidazolidinones, which fall within the scope of the general formula I and their pharmaceutical forms of suitable additive salts with acids, wherein R1 and R2 are as defined herein, in particular for the prevention or treatment of diseases of bacterial nature. The invention further introduces the use of compounds according to the invention for the manufacture of a medication useful for the treatment of various conditions as described above.

  该发明介绍了芳香基咪唑烷酮的新衍生物，其属于一般式I范围内，以及它们与酸适当添加盐的药用形式，其中R1和R2如本文所定义，特别用于预防或治疗细菌性疾病。该发明进一步介绍了根据该发明的化合物用于制造用于治疗上述各种疾病的药物的用途。
• Cook et al., Journal of the Chemical Society, 1950, p. 1892,1896
  作者：Cook et al.

  DOI：——

  日期：——
• A Novel Synthesis of Some New Imidazothiazole and Glycocyamidine Derivatives and Studies on Their Antimicrobial Activities
  作者：Asmaa A. Magd El-Din、Hanaa F. Roaiah、Salwa A. Elsharabasy、Aisha Y. Hassan

  DOI：10.1080/10426500601013224

  日期：2007.4.1

  5,5-diphenyl-2-thioxoimidazolidin-4-one (1) reacted with chloroacetic acid 2a and ethyl chloroacetate 2b in an alkaline medium to afford 2-(4,5-dihydro-5-oxo-4,4-diphenyl-1H-imidazol-2 ylthio)acetic acid (3a) and ethyl 2-(4,5-dihydro-5-oxo-4,4diphenyl-1H-imidazol-2 ylthio)acetate (3b), respectively. Compounds 3a,b were converted to 5,5-diphenylimidazolidine-2,4-dione (4) by boiling in ethanolic hydrochloric acid. When compounds 3a,b were treated with polyphosphoric acid, cyclization occurred, and 6,6-diphenylimidazo[2,1-b]thiazole 3,5(2H,6H)-dione (5) was obtained.2-(methylthio)-1H-imidazol-5(4H)-one derivatives (a,b reacted with hydrazine hydrate to give the corresponding hydrazones 7a,b. The reaction of 6a,b with hydrazine hydrate afforded 3-amino-2-phenylimino imidazolidin-4-one derivatives 10a,b. The antimicrobial activities of compounds 1. 3ab, 5, 7ab, and 10a,b were studied.