2,2'-(benzene-1,4-diylbis{(Z)methylidene[(5Z)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl-5-ylidene]})diacetic acid

• 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: 2,2'-(benzene-1,4-diylbis{(Z)methylidene[(5Z)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl-5-ylidene]})diacetic acid
• 英文别名: 2-[(5Z)-5-[[4-[(Z)-[3-(carboxymethyl)-4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene]methyl]phenyl]methylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
• 化学式: C₁₈H₁₂N₂O₆S₄
• 分子量: 480.567
• InChiKey: JXFGHXUVRFXDAH-CBIKUMSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  230
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-羧甲基绕丹宁 、 对苯二甲醛 在 sodium acetate 、 溶剂黄146 作用下， 反应 4.0h， 以93%的产率得到2,2'-(benzene-1,4-diylbis{(Z)methylidene[(5Z)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl-5-ylidene]})diacetic acid
  参考文献：
  名称：

  Prospective Study Directed to the Synthesis of Symmetrical Linked Bis-Rhodanine Derivatives with Their Antimicrobial Activity

  摘要：

  One-pot three-component reactions of diamines, carbon disulfide and dialkyl acetylenedicarboxylates under conventional or ultrasound methods furnishing bis-rhodanines in good yields are described. Knoevenagel condensation reaction between 5,5-methylene-bis-salicyaldehyde, pyrazole-3,5-dicarbaldehyde or terephthalaldehyde and N-alkylrhodanines afforded bis-arylidenerhodanines. While, the condensation between 2,6-diformylphenols and N-alkylrhodanines furnished only the mono-arylidenerhodanines. The newly synthesized compounds were characterized by HRMS and NMR spectral data. The compounds were screened for their in vitro antimicrobial activities. All the tested compounds showed pronounced activities, suggesting that the rhodanine moiety plays an important role in enhancing the antimicrobial properties of this class of compounds.

  DOI：

  10.3987/com-16-13479

文献信息

• Prospective Study Directed to the Synthesis of Symmetrical Linked Bis-Rhodanine Derivatives with Their Antimicrobial Activity
  作者：Wael A. A. Arafa、Raafat M. Shaker、Saleh A. Rabeh

  DOI：10.3987/com-16-13479

  日期：——

  One-pot three-component reactions of diamines, carbon disulfide and dialkyl acetylenedicarboxylates under conventional or ultrasound methods furnishing bis-rhodanines in good yields are described. Knoevenagel condensation reaction between 5,5-methylene-bis-salicyaldehyde, pyrazole-3,5-dicarbaldehyde or terephthalaldehyde and N-alkylrhodanines afforded bis-arylidenerhodanines. While, the condensation between 2,6-diformylphenols and N-alkylrhodanines furnished only the mono-arylidenerhodanines. The newly synthesized compounds were characterized by HRMS and NMR spectral data. The compounds were screened for their in vitro antimicrobial activities. All the tested compounds showed pronounced activities, suggesting that the rhodanine moiety plays an important role in enhancing the antimicrobial properties of this class of compounds.