4,4'-bis(2-thioxo-4-thiazolidinon-3-yl)diphenylsulfone | 54468-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-bis(2-thioxo-4-thiazolidinon-3-yl)diphenylsulfone
• 英文别名: 3-[4-[4-(4-Oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)phenyl]sulfonylphenyl]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 54468-63-2
• 化学式: C₁₈H₁₂N₂O₄S₅
• 分子量: 480.634
• InChiKey: UCHCJYXJVVQHAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  198
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,4'-bis(2-thioxo-4-thiazolidinon-3-yl)diphenylsulfone 、 4-甲氧基苯甲醛 在 哌啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以76%的产率得到4,4'-bis[5(4-methoxybenzylidene)-2-thioxo-4-thiazolidinon-3-yl]diphenylsulfone
  参考文献：
  名称：

  Synthesis, characterization and in vitro antimicrobial activity of novel 2-thioxo-4-thiazolidinones and 4,4′-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfones

  摘要：

  2-Thioxo-4-thiazolidinones (3a,b) were achieved by cyclocondensation of isothiocyanatosulfonamides (1a,b) with sulfanylacetic acid at reflux temperature in dioxane in the presence of triethylamine. Compound (3a) was exploited to synthesize the versatile hitherto unknown 2-thioxo-4-thiazolidinones (5-10) via its reaction with some electrophiles. Cyclization of 4,4'-diisothiocyanate diphenylsulfone (11) with sulfanylacetic acid furnished 4,4'-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfone (12) which on treatment with excess 4-methoxybenzaldehyde in refluxing dioxane in the presence of piperidine yielded the bisbenzylidene derivative (13). The novel synthesized compounds were characterized by IR, H-1 NMR and mass spectral studies. All the synthesized compounds were screened in vitro for their antibacterial and antifungal activities. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.005
• 作为产物：
  描述：

  双(4-异硫氰酸苯基)砜 、 巯基乙酸 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以70%的产率得到4,4'-bis(2-thioxo-4-thiazolidinon-3-yl)diphenylsulfone
  参考文献：
  名称：

  Synthesis, characterization and in vitro antimicrobial activity of novel 2-thioxo-4-thiazolidinones and 4,4′-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfones

  摘要：

  2-Thioxo-4-thiazolidinones (3a,b) were achieved by cyclocondensation of isothiocyanatosulfonamides (1a,b) with sulfanylacetic acid at reflux temperature in dioxane in the presence of triethylamine. Compound (3a) was exploited to synthesize the versatile hitherto unknown 2-thioxo-4-thiazolidinones (5-10) via its reaction with some electrophiles. Cyclization of 4,4'-diisothiocyanate diphenylsulfone (11) with sulfanylacetic acid furnished 4,4'-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfone (12) which on treatment with excess 4-methoxybenzaldehyde in refluxing dioxane in the presence of piperidine yielded the bisbenzylidene derivative (13). The novel synthesized compounds were characterized by IR, H-1 NMR and mass spectral studies. All the synthesized compounds were screened in vitro for their antibacterial and antifungal activities. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.005

文献信息

• Synthesis, characterization and in vitro antimicrobial activity of novel 2-thioxo-4-thiazolidinones and 4,4′-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfones
  作者：Mohamed S.A. El-Gaby、Gameel A.M. El-Hag Ali、Ahmed A. El-Maghraby、Mohamed T. Abd El-Rahman、Mohamed H.M. Helal

  DOI：10.1016/j.ejmech.2009.05.005

  日期：2009.10

  2-Thioxo-4-thiazolidinones (3a,b) were achieved by cyclocondensation of isothiocyanatosulfonamides (1a,b) with sulfanylacetic acid at reflux temperature in dioxane in the presence of triethylamine. Compound (3a) was exploited to synthesize the versatile hitherto unknown 2-thioxo-4-thiazolidinones (5-10) via its reaction with some electrophiles. Cyclization of 4,4'-diisothiocyanate diphenylsulfone (11) with sulfanylacetic acid furnished 4,4'-bis(2-thioxo-4-thiazolidinone-3-yl)diphenylsulfone (12) which on treatment with excess 4-methoxybenzaldehyde in refluxing dioxane in the presence of piperidine yielded the bisbenzylidene derivative (13). The novel synthesized compounds were characterized by IR, H-1 NMR and mass spectral studies. All the synthesized compounds were screened in vitro for their antibacterial and antifungal activities. (C) 2009 Elsevier Masson SAS. All rights reserved.