(4R)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)thiazolidine-4-carboxylic acid | 197805-74-6

• 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-(3,5-di-tert-butyl-4-hydroxyphenyl)thiazolidine-4-carboxylic acid
• 英文别名: (4R)-2-(3,5-di-tert-butyl-4hydroxyphenyl)-4-thiazolidine carboxylic acid；(4R)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-thiazolidine carboxylic acid；(4R)-2-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3-thiazolidine-4-carboxylic acid
• CAS: 197805-74-6
• 化学式: C₁₈H₂₇NO₃S
• 分子量: 337.483
• InChiKey: OUZHFBTVVJHZHZ-CFMCSPIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  94.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)thiazolidine-4-carboxylic acid 、 二碳酸二叔丁酯 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以87%的产率得到(4R)-3-(tert-butoxycarbonyl)-2-(3,5-di-tert-butyl-4-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：

  DL-半胱氨酸 、 3,5-二叔丁基-4-羟基苯甲醛 以 甲醇 为溶剂， 以22%的产率得到(4R)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Thiazolidine-4-carboxylic acid derivatives as cytoprotective agents

  摘要：

  抗细胞保护剂的化合物被披露。这些化合物具有双重活性，包含一个选择具有抗氧化或清除自由基性质的酚部分和一个选择作为半胱氨酸前药的噻唑啉-4-羧酸酯部分。

  公开号：

  US05846988A1

文献信息

• THIAZOLIDINE-4-CARBOXYLIC ACID DERIVATIVES AS CYTOPROTECTIVE AGENTS
  申请人：ALCON LABORATORIES, INC.

  公开号：EP0842165B1

  公开（公告）日：2001-05-16
• US5846988A
  申请人：——

  公开号：US5846988A

  公开（公告）日：1998-12-08
• 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.
• Thiazolidine-4-carboxylic acid derivatives as cytoprotective agents
  申请人：Alcon Laboratories, Inc.

  公开号：US05846988A1

  公开（公告）日：1998-12-08

  Compounds useful as cytoprotective agents are disclosed. The compounds possess dual activity, containing a phenolic portion selected to have antioxidant or free radical scavenging properties and a thiazolidine-4-carboxylate portion selected for its potential to act as a cysteine prodrug.

  抗细胞保护剂的化合物被披露。这些化合物具有双重活性，包含一个选择具有抗氧化或清除自由基性质的酚部分和一个选择作为半胱氨酸前药的噻唑啉-4-羧酸酯部分。