(2RS,4R)-2-dodecylthiazolidine-4-carboxylic acid | 849052-61-5

• 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: (2RS,4R)-2-dodecylthiazolidine-4-carboxylic acid
• 英文别名: (4R)-2-dodecyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 849052-61-5
• 化学式: C₁₆H₃₁NO₂S
• 分子量: 301.494
• InChiKey: QXKDYGRKSBTGMS-MLCCFXAWSA-N

物化性质

• 沸点：
  451.5±40.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  十八胺 、 (2RS,4R)-2-dodecylthiazolidine-4-carboxylic 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， 反应 0.17h， 以69%的产率得到(2RS,4R)-2-dodecylthiazolidine-4-carboxylic acid octadecylamide
  参考文献：
  名称：

  Discovery of 2-Arylthiazolidine-4-carboxylic Acid Amides as a New Class of Cytotoxic Agents for Prostate Cancer

  摘要：

  To improve the selectivity and antiproliferative activity of previously reported serine amide phosphates (SAPs), we designed a new series of 4-thiazolidinone amides, in which the 4-thiazolidinone moiety was introduced as a phosphate mimic. However, these 4-thiazolidinone derivatives demonstrated less cytotoxicity in prostate cancer cells despite improved selectivity over RH7777 cells. To further optimize the thiazolidinone analogues in terms of cytotoxicity and selectivity, we made closely related structural modifications, which led us to the discovery of a new class of 2-arylthiazolidine-4-carboxylic acid amides. These compounds were potent cytotoxic agents with IC50 values in the low micromolar concentration range and demonstrated enhanced selectivity in receptor-negative cells compared to SAPs and 4-thiazolidinone amides.

  DOI：

  10.1021/jm049208b
• 作为产物：
  描述：

  十三醛 、 L-半胱氨酸盐酸盐无水物 以 乙醇 为溶剂， 反应 1.0h， 以71%的产率得到(2RS,4R)-2-dodecylthiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Development of Novel EDG3 Antagonists Using a 3D Database Search and Their Structure−Activity Relationships

  摘要：

  Sphingosine-1-phosphate (SIP) is an intracellular second messenger and an extracellular mediator through endothelial differentiation gene (EDG) receptors, which are a novel class of G-protein-coupled receptors. Although EDG has attracted much attention because of its various roles, no selective agonists or antagonists have yet been developed. This could account for the delay in clarifying the physiological roles of members of the EDG family. Because precise structural information on EDG receptors is not yet available, pharmacophore models were generated based on structural information for SIP using the rational drug design software Catalyst. Novel antagonists, 2-alkylthiazolidine-4-carboxylic acids, were retrieved from a three-dimensional database search using the pharmacophore models, and these showed activity for EDG3. On the basis of their nonphosphoric acid structure, more potent antagonists, 2-(m- or p-heptylphenyl)thiazolidine-4-carboxylic acid, were developed.

  DOI：

  10.1021/jm020080c

文献信息

• Development of Novel EDG3 Antagonists Using a 3D Database Search and Their Structure−Activity Relationships
  作者：Yuuki Koide、Takeshi Hasegawa、Atsuo Takahashi、Akira Endo、Naoki Mochizuki、Masako Nakagawa、Atsushi Nishida

  DOI：10.1021/jm020080c

  日期：2002.10.1

  Sphingosine-1-phosphate (SIP) is an intracellular second messenger and an extracellular mediator through endothelial differentiation gene (EDG) receptors, which are a novel class of G-protein-coupled receptors. Although EDG has attracted much attention because of its various roles, no selective agonists or antagonists have yet been developed. This could account for the delay in clarifying the physiological roles of members of the EDG family. Because precise structural information on EDG receptors is not yet available, pharmacophore models were generated based on structural information for SIP using the rational drug design software Catalyst. Novel antagonists, 2-alkylthiazolidine-4-carboxylic acids, were retrieved from a three-dimensional database search using the pharmacophore models, and these showed activity for EDG3. On the basis of their nonphosphoric acid structure, more potent antagonists, 2-(m- or p-heptylphenyl)thiazolidine-4-carboxylic acid, were developed.
• Discovery of 2-Arylthiazolidine-4-carboxylic Acid Amides as a New Class of Cytotoxic Agents for Prostate Cancer
  作者：Veeresa Gududuru、Eunju Hurh、James T. Dalton、Duane D. Miller

  DOI：10.1021/jm049208b

  日期：2005.4.1

  To improve the selectivity and antiproliferative activity of previously reported serine amide phosphates (SAPs), we designed a new series of 4-thiazolidinone amides, in which the 4-thiazolidinone moiety was introduced as a phosphate mimic. However, these 4-thiazolidinone derivatives demonstrated less cytotoxicity in prostate cancer cells despite improved selectivity over RH7777 cells. To further optimize the thiazolidinone analogues in terms of cytotoxicity and selectivity, we made closely related structural modifications, which led us to the discovery of a new class of 2-arylthiazolidine-4-carboxylic acid amides. These compounds were potent cytotoxic agents with IC50 values in the low micromolar concentration range and demonstrated enhanced selectivity in receptor-negative cells compared to SAPs and 4-thiazolidinone amides.