2-(4-oxo-2-phenylthiazolidin-3-yl)acetamide | 162828-00-4

• 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-(4-oxo-2-phenylthiazolidin-3-yl)acetamide
• 英文别名: 4-Oxo-2-phenyl-3-thiazolidineacetamide；2-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)acetamide
• CAS: 162828-00-4
• 化学式: C₁₁H₁₂N₂O₂S
• 分子量: 236.294
• InChiKey: KWNZRXPYZDAZCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 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：
  88.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-Phenyl-4-oxothiazolidin-3-yl)acetic acid methyl ester 在 sodium hydroxide 、 草酰氯 、 氨 作用下， 以 甲醇 、 苯 为溶剂， 生成 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

文献信息

• THIAZOLIDINONE AMIDES, THIAZOLIDINE CARBOXYLIC ACID AMIDES, AND SERINE AMIDES, INCLUDING POLYAMINE CONJUGATES THEREOF, AS SELECTIVE ANTI-CANCER AGENTS
  申请人：Miller Duane D.

  公开号：US20080255213A1

  公开（公告）日：2008-10-16

  Substituted thiazolidinone carboxylic acid amides and substituted thiazolidine carboxylic acid amides having a structure where the various substituent groups are as defined in the specification. Methods of making these compounds, pharmaceutical compositions containing the compounds, and their use, particularly for treating or preventing cancer, are also disclosed.

  具有结构的取代噻唑烷酮羧酸酰胺和取代噻唑烷羧酸酰胺，其中各种取代基如规范中定义。还披露了制备这些化合物的方法、含有这些化合物的药物组合物，以及它们的用途，特别是用于治疗或预防癌症。
• Versatile Approach To Encoding Combinatorial Organic Syntheses Using Chemically Robust Secondary Amine Tags
  作者：Zhi-Jie Ni、Derek Maclean、Christopher P. Holmes、Martin M. Murphy、Beatrice Ruhland、Jeffrey W. Jacobs、Eric M. Gordon、Mark A. Gallop

  DOI：10.1021/jm960043j

  日期：1996.1.1

  Encoded combinatorial organic synthesis has recently emerged as a powerful tool for the discovery of biologically active compounds from complex chemical libraries. This report describes a new encoding methodology that uses chemically robust secondary amines as tags. These amines are incorporated into an N-[(dialkylcarbamoyl)methyl]glycine-coding oligomer through simple chemistry that is compatible

  编码组合有机合成最近已成为从复杂化学文库中发现生物活性化合物的有力工具。该报告介绍了一种新的编码方法，该方法使用了具有化学稳定性的仲胺作为标签。通过简单的化学方法将这些胺掺入编码N-[（（二烷基氨基甲酰基）甲基]甘氨酸的低聚物中，该化学方法与可用于组合合成的多种聚合物支持的转化反应兼容。在解码过程中，标记聚合物的酸性水解可再生仲胺，其在丹磺酰化后被解析，并通过反相HPLC在亚pi烯水平上检测到。此策略的多功能性在此通过几种代表性杂环化合物类别（包括β-内酰胺类）的成员的编码合成进行证明
• [EN] THIAZOLIDINONE AMIDES, THIAZOLIDINE CARBOXYLIC ACID AMIDES, METHODS OF MAKING, AND USES THEREOF<br/>[FR] AMIDES DE THIAZOLIDINONE, AMIDES D'ACIDE CARBOXYLIQUE DE THIAZOLIDINE, PROCEDES DE FABRICATION ET UTILISATIONS CORRESPONDANTS
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2005049591A1

  公开（公告）日：2005-06-02

  Substituted thiazolidinone carboxylic acid amides and substituted thiazolidine carboxylic acid amides according to formulae (I) and (II) are disclosed where the various substituent groups are as defined in the specification. Methods of making these compounds, pharmaceutical compositions containing the compounds, and their use, particularly for treating or preventing cancer, are also disclosed.

  根据公式(I)和(II)披露了替代噻唑烷酮羧酸酰胺和替代噻唑烷羧酸酰胺，其中各种取代基如规范中所定义。还披露了制备这些化合物的方法，含有这些化合物的药物组合物，以及它们的用途，特别是用于治疗或预防癌症。
• Analogs exhibiting inhibition of cell proliferation, methods of making, and uses thereof
  申请人：Miller D. Duane

  公开号：US20060014740A1

  公开（公告）日：2006-01-19

  Analogs exhibiting inhibition of cell proliferation are provided. Methods of making the analogs are also included. The analogs can be used to treat cancerous conditions such as prostate, breast, and ovarian cancer.

  提供了抑制细胞增殖的类似物。方法包括制备这些类似物。这些类似物可用于治疗癌症状况，如前列腺癌、乳腺癌和卵巢癌。
• Thiazolidinone amides, thiazolidine carboxylic acid amides, methods of making, and uses thereof
  申请人：Miller D. Duane

  公开号：US20060040998A1

  公开（公告）日：2006-02-23

  Substituted thiazolidinone carboxylic acid amides and substituted thiazolidine carboxylic acid amides according to formulae (I) and (II) are disclosed where the various substituent groups are as defined in the specification. Methods of making these compounds, pharmaceutical compositions containing the compounds, and their use, particularly for treating or preventing cancer, are also disclosed.

  本发明公开了根据式（I）和（II）的取代噻唑啉酮羧酸酰胺和取代噻唑啉羧酸酰胺，其中各种取代基团如规范中所定义。还公开了制备这些化合物的方法、含有这些化合物的药物组合物以及它们的用途，特别是用于治疗或预防癌症。