(E)-5-(2-chlorobenzylidene)thiazolidine-2,4-dione | 5376-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (E)-5-(2-chlorobenzylidene)thiazolidine-2,4-dione
• 英文别名: (5E)-5-[(2-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 5376-20-5
• 化学式: C₁₀H₆ClNO₂S
• 分子量: 239.682
• InChiKey: LODOBCLAGUEESL-VMPITWQZSA-N

物化性质

• 熔点：
  195-196 °C
• 沸点：
  616.7±65.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide 、 (E)-5-(2-chlorobenzylidene)thiazolidine-2,4-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到(E)-2-(5-(2-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

  摘要：

  A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, H-1 NMR and C-13 NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 A mu M).

  DOI：

  10.1007/s00044-015-1358-0
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 2-氯苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以77%的产率得到(E)-5-(2-chlorobenzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

  摘要：

  A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, H-1 NMR and C-13 NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 A mu M).

  DOI：

  10.1007/s00044-015-1358-0

文献信息

• Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities
  作者：Faiyazalam M. Shaikh、Navin B. Patel、Giuseppina Sanna、Bernardetta Busonera、Paolo La Colla、Dhanji P. Rajani

  DOI：10.1007/s00044-015-1358-0

  日期：2015.8

  A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, H-1 NMR and C-13 NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 A mu M).