2-(4-hydroxyphenyl)-3-(2-(piperidin-1-yl)ethyl)thiazolidin-4-one | 1443534-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-hydroxyphenyl)-3-(2-(piperidin-1-yl)ethyl)thiazolidin-4-one
• 英文别名: 2-(4-Hydroxyphenyl)-3-(2-piperidin-1-ylethyl)-1,3-thiazolidin-4-one；2-(4-hydroxyphenyl)-3-(2-piperidin-1-ylethyl)-1,3-thiazolidin-4-one
• CAS: 1443534-62-0
• 化学式: C₁₆H₂₂N₂O₂S
• 分子量: 306.429
• InChiKey: YJWLLMVETFPTCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-氨乙基)哌啶 、 对羟基苯甲醛 、 巯基乙酸 以 甲苯 为溶剂， 反应 5.0h， 以53%的产率得到2-(4-hydroxyphenyl)-3-(2-(piperidin-1-yl)ethyl)thiazolidin-4-one
  参考文献：
  名称：

  Synthesis, antifungal and cytotoxic activities of 2-aryl-3-((piperidin-1-yl)ethyl)thiazolidinones

  摘要：

  A series of sixteen novel thiazolidinone derivatives were synthesized from the efficient one-pot reaction of 2-(piperidin-1-yl)ethylamine, arenealdehydes and mercaptoacetic acid in good yields. Identification and characterization of products were achieved by NMR and GC MS techniques. The in vitro antifungal activities of all synthesized compounds were evaluated against seven fungi: Candida albicans, Candida parapsilosis, Candida guilliermondii, Cryptococcus laurentii, Geotrichum sp, Trichosporon asahii and Rhodotorula sp. The results are expressed as the Minimum Inhibitory Concentration (MIC) and Minimum Fungicidal Concentration (MFC) and the best results were found against the Rhodotorula sp yeast. Two thiazolidinones (4h and 4l), MIC and MFC (16.5 mu g/mL) proved to be 1.6 times more active than fluconazole and four of them (4b, 4e, 4g and 4k (MIC and MFC 25 mu g/mL)) showed similar activity of standard drug to Rhodotorula sp. In addition, the cytotoxicity of thiazolidinones 4a-p was evaluated on cultured Vero cells and most of them displayed low toxicity (above 98 mu g/mL). These preliminary and important results could be considered a starting point for the development of new antifungal agents. (C)2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.030

文献信息

• Synthesis, antifungal and cytotoxic activities of 2-aryl-3-((piperidin-1-yl)ethyl)thiazolidinones
  作者：Alice Kunzler、Patrícia D. Neuenfeldt、Adriana M. das Neves、Claudio M.P. Pereira、Gabriela H. Marques、Patrícia S. Nascente、Maureen H.V. Fernandes、Silvia O. Hübner、Wilson Cunico

  DOI：10.1016/j.ejmech.2013.03.030

  日期：2013.6

  A series of sixteen novel thiazolidinone derivatives were synthesized from the efficient one-pot reaction of 2-(piperidin-1-yl)ethylamine, arenealdehydes and mercaptoacetic acid in good yields. Identification and characterization of products were achieved by NMR and GC MS techniques. The in vitro antifungal activities of all synthesized compounds were evaluated against seven fungi: Candida albicans, Candida parapsilosis, Candida guilliermondii, Cryptococcus laurentii, Geotrichum sp, Trichosporon asahii and Rhodotorula sp. The results are expressed as the Minimum Inhibitory Concentration (MIC) and Minimum Fungicidal Concentration (MFC) and the best results were found against the Rhodotorula sp yeast. Two thiazolidinones (4h and 4l), MIC and MFC (16.5 mu g/mL) proved to be 1.6 times more active than fluconazole and four of them (4b, 4e, 4g and 4k (MIC and MFC 25 mu g/mL)) showed similar activity of standard drug to Rhodotorula sp. In addition, the cytotoxicity of thiazolidinones 4a-p was evaluated on cultured Vero cells and most of them displayed low toxicity (above 98 mu g/mL). These preliminary and important results could be considered a starting point for the development of new antifungal agents. (C)2013 Elsevier Masson SAS. All rights reserved.