2-(4-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid | 110078-71-2

• 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-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid
• 英文别名: (2R,4R)-2-(4-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid；(2R,4R)-2-(4-methoxyphenyl)thiazolidine-4-carboxylic acid；(2R,4R)-2-(4-methoxyphenyl)-4-carboxy-1,3-thiazolidine；(2R,4R)-2-(4-methoxyphenyl)-1,3-thiazolidin-3-ium-4-carboxylate
• CAS: 110078-71-2
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: ZQRSXNJVEHLFCE-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-半胱氨酸盐酸盐无水物 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2-(4-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid 、 2-(4-methoxyphenyl)-1,3-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  一些抗氧化剂噻唑烷-4-羧酸的半胱氨酸释放模式

  摘要：

  如果未通过细胞防御机制阻止，则与细胞中自由基浓度显着增加相对应的氧化应激可对关键的生物大分子造成相当大的损害。低分子量巯基谷胱甘肽（GSH）构成主要的细胞内抗氧化剂之一。它是通过合成半胱氨酸，一种由于其神经毒性而仅在细胞中限量发现的氨基酸。因此，为了确保在氧化应激的情况下有效地合成GSH，应在细胞外提供半胱氨酸。然而，考虑到其亲核性质并迅速转化成胱氨酸，其相应的二硫键，半胱氨酸具有一定的毒性，因此通常在前药方法中进行补充。在此，一些噻唑烷-4-羧酸的合成和评价它们的抗氧化特性通过DDPH和CUPRAC分析。然后，在水性和有机介质中研究所得化合物的半胱氨酸释放能力，以使分子的相关抗氧化特性与其半胱氨酸释放模式相关联。结果，该结构的抗氧化性能不仅归因于半胱氨酸的释放，还归因于噻唑烷循环本身。

  DOI：

  10.1016/j.ejmech.2016.03.019

文献信息

• Crystal structure, computational studies, and stereoselectivity in the synthesis of 2-aryl-thiazolidine-4-carboxylic acids via <i>in situ</i> imine intermediate
  作者：Rohidas M. Jagtap、Masood A. Rizvi、Yuvraj B. Dangat、Satish K. Pardeshi

  DOI：10.1080/17415993.2016.1156116

  日期：2016.7.3

  and diastereomeric excess (de%) have been investigated. A plausible mechanism for stereoselectivity via an in situ imine intermediate is proposed using real-time IR monitoring of the synthetic reaction based on the significant signals at 1597, 1593 cm−1 for imine (C=N) stretching. The imine mechanism for stereoselectivity was further supported by NMR studies of azomethine 13C NMR signals at 159, 160 δ ppm

  摘要本文介绍了通过在芳香醛上亲核加成 L-半胱氨酸合成 (2R/2S,4R)-2-芳基-噻唑烷-4-羧酸，包括在含水 DMSO 介质中的产率和时间有效的室温反应在 NaHCO3 作为碱存在下。通过液相色谱-质谱分析对合成的非对映体进行光谱表征和量化非对映体过量。研究了芳香醛中取代基的类型和位置对反应时间、产率百分比、新形成的手性中心 [C(2)-H] 的 1H NMR 位移和非对映体过量 (de%) 的影响。基于 1597 处的显着信号，使用合成反应的实时红外监测，提出了通过原位亚胺中间体产生立体选择性的合理机制，1593 cm-1 用于亚胺 (C=N) 拉伸。立体选择性的亚胺机制得到了 159、160 δ ppm 的偶氮甲碱 13C NMR 信号的 NMR 研究以及迄今为止未知的 (2S,4R)-3-(叔丁氧基羰基)-2-(2-羟基苯基)噻唑烷-4-羧酸(3a)作为合成(2R/2S,4R
• Conformational analysis, spectral and catalytic properties of 1,3-thiazolidines, ligands for acetophenone hydrosilylation with diphenylsilane
  作者：A. N. Skvortsov、V. M. Uvarov、D. A. de Vekki、E. P. Studentsov、N. K. Skvortsov

  DOI：10.1134/s107036321010021x

  日期：2010.10

  2-Aryl- and 2-furyl-4-carboxy-1,3-thiazolidines were synthesized. Their spectral properties were studied, and conformational analysis was performed. It was shown that they exist in solution as an equilibrium of neutral and zwitter-ion forms. The influence of the nature of substitutents and of their location in a benzene ring of thiazolidines as ligands of rhodium complexes on acetophenone hydrosilylation with diphenylsilane was examined. Thiazolidines containing donor substituents in the para-position of the benzene ring were found to be the most effective; maximal asymmetrical induction (55% ee) was reached in the presence of 2-(4-methoxyphenyl)-4-carboxy-1,3-thiazolidine.
• Targeting triple-negative breast cancer cells with 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles
  作者：Kathleen Santos、Mafalda Laranjo、Ana Margarida Abrantes、Ana F. Brito、Cristina Gonçalves、Ana Bela Sarmento Ribeiro、M. Filomena Botelho、Maria I.L. Soares、Andreia S.R. Oliveira、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.ejmech.2014.04.008

  日期：2014.5

  Further studies on 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles as anticancer agents against breast cancer are reported, allowing to demonstrate the potential of these compounds for the therapy of the triple-negative breast cancer, the most challenging tumors in clinical practice. These compounds were assayed for their in vitro cytotoxicity on several human breast cancer cell lines (MCF7, HCC1954 and HCC1806 cell lines). Particularly interesting were the results obtained for 4-hydroxyphenyl substituted derivative, which proved to be the most promising compound regarding HCC1806 cell line, a triple-negative breast cancer. The effects of the two most active compounds on cell survival, viability, cell cycle, DNA damage and expression of proteins related to cell death pathways were studied. The reported results consolidate the potential of 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles for the therapy of breast cancer, particularly the triple-negative. (c) 2014 Elsevier Masson SAS. All rights reserved.