[2-(2,6-Dichloro-phenyl)-4-oxo-thiazolidin-3-yl]-acetic acid | 793669-16-6

• 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-(2,6-Dichloro-phenyl)-4-oxo-thiazolidin-3-yl]-acetic acid
• 英文别名: 2-[2-(2,6-Dichlorophenyl)-4-oxo-thiazolidin-3-yl]acetic acid；2-[2-(2,6-dichlorophenyl)-4-oxo-1,3-thiazolidin-3-yl]acetic acid
• CAS: 793669-16-6
• 化学式: C₁₁H₉Cl₂NO₃S
• 分子量: 306.169
• InChiKey: PCEIEFSDXILWMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  十八胺 、 [2-(2,6-Dichloro-phenyl)-4-oxo-thiazolidin-3-yl]-acetic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-(2,6-dichlorophenyl)-4-oxothiazolidin-3-yl)-N-octadecylacetamide
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer

  摘要：

  We have previously described serine amide phosphates (SAPs) as a novel class of cytotoxic agents for prostate cancer. Several of them showed potent cytotoxicity against human prostate cancer cell lines, but were not selective in non-tumor cells. To improve the selectivity and further enhance the potency, we designed a new series of 2-aryl-4-oxo-thiazolidin-3-yl amides. The current work describes synthesis, SAR, and biological evaluation of these compounds for their ability to inhibit the growth of prostate cancer cells. The antiproliferative effects of synthesized compounds were examined in five human prostate cancer cell lines (DU-145, PC-3, LNCaP, PPC-1, and TSU), and in RH7777 cells (negative controls). From this study, three potent compounds (8, 20, and 21) have been detected, which are effective in killing prostate cancer cells with improved selectivity compared to SAPs. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.08.029
• 作为产物：
  描述：

  2,6-二氯苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 [2-(2,6-Dichloro-phenyl)-4-oxo-thiazolidin-3-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer

  摘要：

  We have previously described serine amide phosphates (SAPs) as a novel class of cytotoxic agents for prostate cancer. Several of them showed potent cytotoxicity against human prostate cancer cell lines, but were not selective in non-tumor cells. To improve the selectivity and further enhance the potency, we designed a new series of 2-aryl-4-oxo-thiazolidin-3-yl amides. The current work describes synthesis, SAR, and biological evaluation of these compounds for their ability to inhibit the growth of prostate cancer cells. The antiproliferative effects of synthesized compounds were examined in five human prostate cancer cell lines (DU-145, PC-3, LNCaP, PPC-1, and TSU), and in RH7777 cells (negative controls). From this study, three potent compounds (8, 20, and 21) have been detected, which are effective in killing prostate cancer cells with improved selectivity compared to SAPs. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.08.029

文献信息

• A DIC mediated expeditious small library synthesis and biological activity of thiazolidin-4-one and 1,3-thiazinan-4-one derivatives
  作者：Amit Verma、Shweta S Verma、Shailendra K Saraf

  DOI：10.1002/jhet.429

  日期：——

  A diisopropylcarbodiimide (DIC) mediated small library of thiazolidin‐4‐one and 1,3‐Thiazinan‐4‐one derivatives were efficiently synthesized using one pot three component condensation of amino acid, aldehyde, and mercapto carboxylic acid on a polymer support. The study shows significantly higher yields of the thiazolidin‐4‐one derivatives thereby indicating a lower dependence on the nature of the amino

  使用一锅三组分的氨基酸，醛和巯基羧酸在聚合物载体上的缩合反应，可以高效地合成由二异丙基碳二亚胺（DIC）介导的噻唑烷丁4-1和1,3-噻嗪南4-1衍生物的小型文库。这项研究表明，噻唑烷酮-4-酮衍生物的收率高得多，从而表明对氨基酸和醛组分的性质的依赖性降低。作为该方案的明显扩展，反应是使用杂环醛和取代的受阻芳族醛代替简单的芳族醛进行的。还针对这些三种病原性真菌筛选了合成的文库化合物的抗真菌活性：白色念珠菌（Candida albicans，Ca），副念珠菌（Candida parapsilosis）（Cp）和新型隐球菌（Cn）。J.杂环化​​学。（2010）。