(Z)-5-(2-α,α,α-trifluoromethylbenzylidene)-2-thioxothiazolidin-4-one

• 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: (Z)-5-(2-α,α,α-trifluoromethylbenzylidene)-2-thioxothiazolidin-4-one
• 英文别名: (Z)-2-thioxo-5-(2-(trifluoromethyl)benzylidene)thiazolidin-4-one；(5Z)-2-sulfanyl-5-[2-(trifluoromethyl)benzylidene]-1,3-thiazol-4(5H)-one；(5Z)-2-sulfanylidene-5-[[2-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidin-4-one
• 化学式: C₁₁H₆F₃NOS₂
• mdl: MFCD04969074
• 分子量: 289.302
• InChiKey: YAFQKXSDJFTZRD-YVMONPNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  罗丹宁 、 邻三氟甲基苯甲醛 反应 0.05h， 以55%的产率得到(Z)-5-(2-α,α,α-trifluoromethylbenzylidene)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Synthesis and antifungal activity of (Z)-5-arylidenerhodanines

  摘要：

  An efficient microwave-assisted synthesis of new (Z)-5-arylidenerhodanines under solvent-free conditions is described and their in vitro antifungal activity was evaluated following the CLSI (formerly NCCLS) guidelines against a panel of both standardized and clinical opportunistic pathogenic fungi. An analysis of the structure-activity relationship (SAR) along with computational studies showed that the most active compounds (F- and CF3-substituted rbodanines) possess high log P values and low polarizability. Mechanism-based assays suggest that active compounds neither would bind to ergosterol nor would produce a damage to the fungal membrane. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.038

文献信息

• Synthesis and antifungal activity of (Z)-5-arylidenerhodanines
  作者：Maximiliano Sortino、Paula Delgado、Sabina Juárez、Jairo Quiroga、Rodrigo Abonía、Braulio Insuasty、Manuel Nogueras、Laura Rodero、Francisco M. Garibotto、Ricardo D. Enriz

  DOI：10.1016/j.bmc.2006.09.038

  日期：2007.1.1

  An efficient microwave-assisted synthesis of new (Z)-5-arylidenerhodanines under solvent-free conditions is described and their in vitro antifungal activity was evaluated following the CLSI (formerly NCCLS) guidelines against a panel of both standardized and clinical opportunistic pathogenic fungi. An analysis of the structure-activity relationship (SAR) along with computational studies showed that the most active compounds (F- and CF3-substituted rbodanines) possess high log P values and low polarizability. Mechanism-based assays suggest that active compounds neither would bind to ergosterol nor would produce a damage to the fungal membrane. (c) 2006 Elsevier Ltd. All rights reserved.