(4R)-2-(5-fluoro-2-hydroxyphenyl)thiazolidine-4-carboxylic acid | 1188543-73-8

• 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: (4R)-2-(5-fluoro-2-hydroxyphenyl)thiazolidine-4-carboxylic acid
• 英文别名: (4R)-2-(5-fluoro-2-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid
• CAS: 1188543-73-8
• 化学式: C₁₀H₁₀FNO₃S
• 分子量: 243.259
• InChiKey: ULTIKEAFZABDTH-JAVCKPHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  16
• 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：
  94.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (4R)-2-(5-fluoro-2-hydroxyphenyl)thiazolidine-4-carboxylic acid 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以93%的产率得到(4R)-3-(tert-butoxycarbonyl)-2-(5-fluoro-2-hydroxyphenyl)thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Synthesis, structure and structure–activity relationship analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives as potential antibacterial agents

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2009.04.014
• 作为产物：
  描述：

  L-半胱氨酸 、 5-氟水杨醛 以 乙醇 为溶剂， 反应 8.0h， 以90%的产率得到(4R)-2-(5-fluoro-2-hydroxyphenyl)thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Synthesis, characterization and antibacterial activities of N-tert-butoxycarbonyl-thiazolidine carboxylic acid

  摘要：

  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。

  DOI：

  10.1039/c4ra15284k

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。
• 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.