L-2-(4-溴苯基)-1,3-噻唑烷-4-羧酸 | 294866-41-4

• 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
• 中文名称: L-2-(4-溴苯基)-1,3-噻唑烷-4-羧酸
• 英文名称: (2RS,4R)-2-(4-bromophenyl)-1,3-thiazolidine-4-carboxylic acid
• 英文别名: (2RS,4R)-2-(4-bromophenyl)-thiazolidine-4-carboxylic acid；(4R)-2-(4-bromophenyl)thiazolidine-4-carboxylic acid；(4R)-2-(4-bromophenyl)-1,3-thiazolidine-4-carboxylic acid
• CAS: 294866-41-4
• 化学式: C₁₀H₁₀BrNO₂S
• 分子量: 288.165
• InChiKey: TYLJHTCYCWHWRG-IENPIDJESA-N

物化性质

• 沸点：
  474.0±45.0 °C(Predicted)
• 密度：
  1.629±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 L-2-(4-溴苯基)-1,3-噻唑烷-4-羧酸 以 吡啶 为溶剂， 反应 8.0h， 以82%的产率得到(2S,4R)-3-acetyl-2-(4-bromophenyl)-1,3-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Gyoergydeak, Zoltan; Kajtar-Peredy, Maria; Kajtar, Judit, Liebigs Annalen der Chemie, 1987, p. 927 - 934

  摘要：

  DOI：
• 作为产物：
  描述：

  L-半胱氨酸 、 对溴苯甲醛 以 乙醇 、 水 为溶剂， 反应 6.0h， 以87%的产率得到L-2-(4-溴苯基)-1,3-噻唑烷-4-羧酸
  参考文献：
  名称：

  半胱氨酸及其衍生物作为新型抗病毒和抗真菌药物的发现

  摘要：

  基于天然产物半胱氨酸的结构，设计合成了一系列噻唑烷-4-羧酸。所有带有噻唑烷-4-甲酸的目标化合物均通过 1H-NMR、13C-NMR 和 HRMS 技术进行了表征。在体外和体内评估了半胱氨酸及其衍生物的抗病毒和抗真菌活性。抗TMV活性结果表明，所有化合物在浓度为500 μg/mL时均表现出中等至优异的抗烟草花叶病毒（TMV）活性。化合物半胱氨酸 (1)、3-4、7、10、13、20、23 和 24 比商业植物杀病毒剂利巴韦林表现出更高的抗 TMV 活性（抑制率：40%、40% 和 38%，500 μg/ mL，分别用于体内灭活、治疗和保护活性），特别是化合物 3（500 μg/mL 时，体内灭活、治疗和保护活性的抑制率分别为 51%、47% 和 49%）优异的抗病毒活性成为新的抗病毒候选药物。TEM抗病毒机制研究表明，化合物3可以通过聚集20S蛋白盘来抑制病毒组装。分子对接结果显示，抗病

  DOI：

  10.3390/molecules26020383

文献信息

• Synthesis, characterization and antibacterial activities of N-tert-butoxycarbonyl-thiazolidine carboxylic acid
  作者：Zhong-Cheng Song、Gao-Yuan Ma、Hai-Liang Zhu

  DOI：10.1039/c4ra15284k

  日期：——

  The mechanism of dynamic kinetic resolution, a nucleophilic substitution through an intramolecular hydrogen bonding by the formation of N-Boc-TCAs was proposed and a qualitative explanation was interpretated according to Curtin–Hammett principle.

  动力学选择性分辨机制是通过形成N-Boc-TCAs的分子内氢键进行亲核取代，根据Curtin-Hammett原理提出了定性解释。
• One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
  作者：Juan Lu、Bin Yao、Desheng Zhan、Zhuo Sun、Yun Ji、Xiaofeng Zhang

  DOI：10.3762/bjoc.18.171

  日期：——

  four-component reaction in one pot as an atom- and step-economic process was developed to synthesize diastereoselectively spirooxindolepyrrolothiazoles through sequential N,S-acetalation of aldehydes with cysteine and decarboxylative [3 + 2] cycloaddition with olefinic oxindoles. High synthetic efficiency, operational simplification and reaction process economy using EtOH as solvent, and only releasing

  开发了一种新型四组分一锅反应，作为一种原子分步经济工艺，通过醛与半胱氨酸的连续N,S-缩醛化和与烯属羟吲哚的脱羧 [3 + 2] 环加成来合成非对映选择性螺环吲哚吡咯并噻唑。使用EtOH作为溶剂且仅释放CO 2和H 2 O作为副产物的高合成效率、操作简化和反应过程经济性使得该方法有利于绿色化学指标分析。
• Acharya, Jiba Raj; Zhang, Huating; Li, Xian, Journal of the American Chemical Society, 2009, vol. 131, p. 880 - 881
  作者：Acharya, Jiba Raj、Zhang, Huating、Li, Xian、Nesterov, Evgueni E.

  DOI：——

  日期：——
• 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.
• Synthesis, structure and structure–activity relationship analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives as potential antibacterial agents
  作者：Zhong-Cheng Song、Gao-Yuan Ma、Peng-Cheng Lv、Huan-Qiu Li、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2009.04.014

  日期：2009.10

  Nine 2-arylthiazolidine-4-carboxylic acid derivatives and nine 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives were synthesized to screen for their antibacterial activities. Compounds S, 14-18 were first reported. Their chemical structures were clearly determined by H-1 NMR, C-13 NMR, ESI mass spectra and elemental analyses, coupled with one selected single-crystal structure. All the compounds were assayed for antibacterial activities against two Gram-positive bacterial strains (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and two Gram-negative bacterial strains (Escherichia coli ATCC 35218 and Pseudomonas aeruginosa ATCC 13525) by MTT method. Most of the 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives exhibited better antibacterial activities against the four bacterial strains than relative 2-arylthiazolidine-4-carboxylic acid derivatives. Compound (2RS,4R)-3-(tert-butoxycarbonyl)-2-(5-fluoro-2-hydroxyphenyl)thiazolidine-4-carboxylic acid (14) showed powerful antibacterial activities against P aeruginosa with IC50 value of 0.195 mu g/mL, which was superior to the positive controls Penicillin G and Kanamycin B, respectively. On the basis of the biological results, structure-activity relationships were discussed. (C) 2009 Elsevier Masson SAS. All rights reserved.