2-(2-Phenyl-4-oxothiazolidin-3-yl)acetic acid methyl ester | 171974-79-1

• 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-Phenyl-4-oxothiazolidin-3-yl)acetic acid methyl ester
• 英文别名: Methyl 2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetate
• CAS: 171974-79-1
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: XFWIMOIOYXCGCF-UHFFFAOYSA-N

物化性质

• 沸点：
  452.4±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Phenyl-4-oxothiazolidin-3-yl)acetic acid methyl ester 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(3, 5-bis (trifluoromethyl) phenyl)-2-(4-oxo-2-phenylthiazolidin-3-yl) acetamide
  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：

  甘氨酸甲酯盐酸盐 、 苯甲醛 、 巯基乙酸 在 4 A molecular sieve 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以80%的产率得到2-(2-Phenyl-4-oxothiazolidin-3-yl)acetic acid methyl ester
  参考文献：
  名称：

  4-噻唑烷酮的高效微波增强合成

  摘要：

  已经开发了一种微波增强、快速、三组分一锅缩合方法，用于在大气压下在开放容器中使用环境友好的溶剂乙醇合成 4-噻唑烷酮。应用该方法以良好的收率合成了十种不同的 4-噻唑烷酮。

  DOI：

  10.1055/s-2004-832811

文献信息

• The First Solvent-Free, Microwave-Accelerated, Three-Component Synthesis of Thiazolidin-4-ones via One-Pot Tandem Staudinger/aza-Wittig Reaction
  作者：Poovan Shanmugavelan、Murugan Sathishkumar、Sangaraiah Nagarajan、Raja Ranganathan、Alagusundaram Ponnuswamy

  DOI：10.1002/jhet.1705

  日期：2014.7

  An efficient and rapid, solvent‐free, microwave‐accelerated, one‐pot, three‐component protocol for thiazolidin‐4‐ones synthesis from organic azides has been reported for the first time via Staudinger/aza‐Wittig reaction. The microwave‐accelerated, solvent‐free approach overcomes the limitations associated with the prevailing solution phase methodologies. In particular, its novelty is that it eradicates

  首次通过Staudinger / aza-Wittig反应报道了一种有效，快速，无溶剂，微波加速，一锅，三组分的有机叠氮化物合成噻唑烷酮-4酮的方法。微波加速，无溶剂的方法克服了与现行溶液相方法学相关的局限性。特别地，其新颖性在于它消除了重要的限制，即已知会影响反应收率和反应速率的水（副产物）的积累。因此，已在短时间内合成了噻唑烷酮-4-酮文库，收率极高（92-96％）。
• Strategies for Combinatorial Organic Synthesis: Solution and Polymer-Supported Synthesis of 4-Thiazolidinones and 4-Metathiazanones Derived from Amino Acids
  作者：Christopher P. Holmes、Jason P. Chinn、Gary C. Look、Eric M. Gordon、Mark A. Gallop

  DOI：10.1021/jo00127a044

  日期：1995.11

  Both the solution and polymer-supported synthesis of 4-thiazolidinones and 4-metathiazanones derived from amino acids are described. Solution studies showed that moderate to high yields of 4-thiazolidinones could be obtained from the one-pot, three-component condensation of amino acid esters (glycine, alanine, beta-alanine, phenylalanine, and valine), an aldehyde (benzaldehyde, o-tolualdehyde, m-tolualdehyde, p-tolualdehyde, and 3-pyridinecarboxaldehyde), and an alpha-mercapto carboxylic acid (thiolactic and mercaptoacetic acid). Acylation of standard peptide synthesis resins with an Fmoc-protected amino acid, followed by deprotection of the Fmoc group and condensation with aldehydes and an alpha-mercapto or beta-mercapto carboxylic acid, lead to the formation of the five- and six-membered heterocycles. The stepwise assembly of 4-thiazolidinones by treatment of the intermediate imine with an alpha-mercapto carboxylic acid was also demonstrated. Cleavage from the support under acidic (trifluoroacetic acid) conditions gave high yields and high purities of the liberated 4-thiazolidinones and lower yields of 4-metathiazanones.
• Synthesis and antiproliferative activity of 2-aryl-4-oxo-thiazolidin-3-yl-amides for prostate cancer
  作者：Veeresa Gududuru、Eunju Hurh、James T. Dalton、Duane D. Miller

  DOI：10.1016/j.bmcl.2004.08.029

  日期：2004.11

  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.
• Efficient Microwave Enhanced Synthesis of 4-Thiazolidinones
  作者：Duane D. Miller、Veeresa Gududuru、Viet Nguyen、James T. Dalton

  DOI：10.1055/s-2004-832811

  日期：——

  A microwave-enhanced, rapid, three-component one-pot condensation method has been developed for the synthesis of 4-thiazolidinones using environmentally benign solvent ethanol in open vessels at atmospheric pressure. Applying this methodology ten different 4-thiazolidinones were synthesized in good yields.

  已经开发了一种微波增强、快速、三组分一锅缩合方法，用于在大气压下在开放容器中使用环境友好的溶剂乙醇合成 4-噻唑烷酮。应用该方法以良好的收率合成了十种不同的 4-噻唑烷酮。