2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)thiazolidin-4-one | 1449794-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)thiazolidin-4-one
• 英文别名: 2-(3,5-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one；2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one
• CAS: 1449794-93-7
• 化学式: C₁₅H₁₃NO₄S
• 分子量: 303.339
• InChiKey: UPZDZVPTSGJXLC-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲醛 、 对氨基苯酚 、 巯基乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.99h， 以63%的产率得到2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and cytotoxic activity evaluation of 2,3-thiazolidin-4-one derivatives on human breast cancer cell lines

  摘要：

  It is well known that resveratrol (RSV) displayed cancer-preventing and anticancer properties but its clinical application is limited because of a low bioavailability and a rapid clearance from the circulation. Aim of this work was to synthesize pharmacologically active resveratrol analogs with an enhanced structural rigidity and bioavailability. In particular, we have synthesized a library of 2,3-thiazolidin-4-one derivatives in which a thiazolidinone nucleus connects two aromatic rings. Some of these compounds showed strong inhibitory effects on breast cancer cell growth. Our results indicate that some of thiazolidin-based resveratrol derivatives may become a new potent alternative tool for the treatment of human breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.051

文献信息

• Synthesis and cytotoxic activity evaluation of 2,3-thiazolidin-4-one derivatives on human breast cancer cell lines
  作者：Marina Sala、Adele Chimento、Carmela Saturnino、Isabel M. Gomez-Monterrey、Simona Musella、Alessia Bertamino、Ciro Milite、Maria Stefania Sinicropi、Anna Caruso、Rosa Sirianni、Paolo Tortorella、Ettore Novellino、Pietro Campiglia、Vincenzo Pezzi

  DOI：10.1016/j.bmcl.2013.06.051

  日期：2013.9

  It is well known that resveratrol (RSV) displayed cancer-preventing and anticancer properties but its clinical application is limited because of a low bioavailability and a rapid clearance from the circulation. Aim of this work was to synthesize pharmacologically active resveratrol analogs with an enhanced structural rigidity and bioavailability. In particular, we have synthesized a library of 2,3-thiazolidin-4-one derivatives in which a thiazolidinone nucleus connects two aromatic rings. Some of these compounds showed strong inhibitory effects on breast cancer cell growth. Our results indicate that some of thiazolidin-based resveratrol derivatives may become a new potent alternative tool for the treatment of human breast cancer. (C) 2013 Elsevier Ltd. All rights reserved.