(S)-3-(4-hydroxyphenyl)-2-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid | 1388204-64-5

• 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: (S)-3-(4-hydroxyphenyl)-2-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid
• 英文别名: (2S)-3-(4-hydroxyphenyl)-2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)propanoic acid
• CAS: 1388204-64-5
• 化学式: C₁₂H₁₁NO₄S₂
• 分子量: 297.356
• InChiKey: MJXXLOVNUUHQQM-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-hydroxyphenyl)-2-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid 、 3-Methyl-1-phenyl-5-[3-(trifluoromethyl)phenoxy]pyrazole-4-carbaldehyde 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-aryloxypyrazole derivatives bearing a rhodanine-3-aromatic acid as potential antimicrobial agents

  摘要：

  Three novel series of 5-aryloxypyrazole derivatives have been synthesized and tested for their antibacterial activity. The majority of the synthesized compounds showed potent inhibitory activity against Gram-positive bacteria Staphylococcus aureus 4220, especially against the strains of multidrug-resistant clinical isolates (MRSA3167/3506 and QRSA3505/3519). Among which compounds IIIb, IIIg and IIIm showed the most potent levels of activity (MIC = 1 mu g/mL) against the multidrug-resistant strains. And cytotoxic activity assay showed that the compounds tested did not affect cell viability on the Human cervical (HeLa) cells at their MICs. The current study therefore suggests that 5-aryloxypyrazoles bearing a rhodanine-3-aromatic acid moiety are promising scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.107
• 作为产物：
  描述：

  L-酪氨酸 在 氨 作用下， 以 水 为溶剂， 反应 16.5h， 生成 (S)-3-(4-hydroxyphenyl)-2-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid
  参考文献：
  名称：

  Efficient Conversion of N-Terminal of L-Tyrosine, DL-Phenyl Alanine, and Glycine to Substituted 2-Thioxo-thiazolidine-4-ones: A Stereospecific Synthesis

  摘要：

  We report facile and efficient conversion of the amino functional group of amino acids such a s L-tyrosine, DL-phenylalanine, and glycine to the corresponding (+/-)-2-t-hioxo-thiazolidine-4-ones (rhodanines). Stereospecific synthesis of amino acid-incorporated rhodanine is achieved in the case of L-tyrosine. Knoevenagel condensation over the active methylene group at the fifth position of the corresponding rhodanines is also described. The substituted rhodanine incorporated with tyrosine in the form of a dimer connected via two-carbon linker possesses significant anticancer activity against A549 cells (human lung cancer cells).

  DOI：

  10.1080/00397911.2011.576322

文献信息

• Synthesis and Bioactivity Evaluation of N-Arylsulfonylindole Analogs Bearing a Rhodanine Moiety as Antibacterial Agents
  作者：Ming-Xia Song、Song-Hui Li、Jiao-Yang Peng、Ting-Ting Guo、Wen-Hui Xu、Shao-Feng Xiong、Xian-Qing Deng

  DOI：10.3390/molecules22060970

  日期：——

  the scarcity of novel agents under development, bacterial infections are still a pressing global problem, making new types of antibacterial agents, which are effective both alone and in combination with traditional antibiotics, urgently needed. In this paper, seven series of N-arylsulfonylindole analogs 5–11 bearing rhodanine moieties were synthesized, characterized, and evaluated for antibacterial

  由于细菌对抗生素的耐药性迅速增长，并且正在开发的新型药物的稀缺性，细菌感染仍然是一个紧迫的全球问题，迫切需要新型抗菌药物，无论是单独使用还是与传统抗生素联合使用都有效。在本文中，合成、表征和评估了七个系列的 N-芳基磺酰基吲哚类似物 5-11 带有罗丹宁部分的抗菌活性。根据体外抗菌结果，一半合成的化合物对四种革兰氏阳性菌显示出有效的抑制作用，MIC 值在 0.5-8 µg/mL 范围内。对于多重耐药菌株，化合物 6a 和 6c 的效力最强，MIC 值为 0.5 µg/mL，与加替沙星的活性相当，
• Synthesis and Evaluation of Chiral Rhodanine Derivatives Bearing Quinoxalinyl Imidazole Moiety as ALK5 Inhibitors
  作者：Chang Ji Zheng、Cheng Hua Jin、Li-Min Zhao、Fang Yan Guo、Hui Min Wang、Tong Dou、Jun Da Qi、Wen Bo Xu、Lianxun Piao、Xuejun Jin、Fen-Er Chen、Hu-Ri Piao

  DOI：10.2174/1573406417666210628144849

  日期：2022.5

  synthesized and evaluated for their ALK5 inhibitory and antimicrobial activity. The structures were confirmed by their 1H NMR, 13C NMR and HRMS spectra. All the synthesized compounds were screened against Grampositive strains, Gram-negative strains, and fungi. RESULTS Among the synthesized compounds, compound 12h showed the highest activity (IC50 = 0.416 μM) against ALK5 kinase. Compound 12h exhibited

  背景技术抑制TGF-β信号通路被认为是预防多种疾病发展的有效方法。在 TGF-β 抑制剂的设计和合成中，发现含有喹喔啉基咪唑部分的罗丹宁化合物具有很强的抗菌活性。目的 这项工作的目的是研究合成的其他手性罗丹宁 TGF-β 抑制剂的抗菌活性。方法 两个系列的3-取代-5-(5-(6-methylpyridin-2-yl)-4-(quinoxalinyl-6-yl)-1Himidazol-2-yl)methylene)-2-thioxothiazolin-4-ones (合成了 12a-h 和 13a-e) 并评估了它们的 ALK5 抑制和抗菌活性。通过它们的 1H NMR、13C NMR 和 HRMS 光谱证实了这些结构。所有合成的化合物都针对革兰氏阳性菌株、革兰氏阴性菌株和真菌进行了筛选。结果在合成的化合物中，化合物12h对ALK5激酶的活性最高（IC50 = 0.416 μM）。化合物 12h
• Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents
  作者：Ming-Xia Song、Chang-Ji Zheng、Xian-Qing Deng、Qing Wang、Shao-Pu Hou、Ting-Ting Liu、Xiao-Lan Xing、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2012.05.023

  日期：2012.8

  Five series of (Z)-5-(4-(2-oxo-2-phenylethoxy)benzylidene)-2-thioxothiazolidin-4-one derivatives (I-V) were synthesized, characterized, and evaluated for their anti-bacterial activity. Most of the synthesized compounds showed potent inhibition against several Gram-positive bacteria (including multidrug-resistant clinical isolates) with MIC values in the range of 1-32 mu g/mL. Compounds IIIi, Vb and Vc presented the most potent activity, showing four-fold more potency than norfloxacin (MIC = 8 mu g/mL and 4 mu g/mL) and 64-fold more activity than oxacillin (MIC > 64 mu g/mL) against MRSA CCARM 3167 and 3506 strains with MIC values of 1 mu g/mL, and 64-fold more potency than norfloxacin (MIC > 64 mu g/mL) and comparable activity to oxacillin (MIC = 1 mu g/mL) against the QRSA CCARM 3505 and 3519 strains. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of 5-aryloxypyrazole derivatives bearing a rhodanine-3-aromatic acid as potential antimicrobial agents
  作者：Chang-Ji Zheng、Ming-Xia Song、Liang-Peng Sun、Yan Wu、Lan Hong、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2012.09.107

  日期：2012.12

  Three novel series of 5-aryloxypyrazole derivatives have been synthesized and tested for their antibacterial activity. The majority of the synthesized compounds showed potent inhibitory activity against Gram-positive bacteria Staphylococcus aureus 4220, especially against the strains of multidrug-resistant clinical isolates (MRSA3167/3506 and QRSA3505/3519). Among which compounds IIIb, IIIg and IIIm showed the most potent levels of activity (MIC = 1 mu g/mL) against the multidrug-resistant strains. And cytotoxic activity assay showed that the compounds tested did not affect cell viability on the Human cervical (HeLa) cells at their MICs. The current study therefore suggests that 5-aryloxypyrazoles bearing a rhodanine-3-aromatic acid moiety are promising scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2012 Elsevier Ltd. All rights reserved.
• Efficient Conversion of <i>N</i>-Terminal of L-Tyrosine, DL-Phenyl Alanine, and Glycine to Substituted 2-Thioxo-thiazolidine-4-ones: A Stereospecific Synthesis
  作者：B. R. Prashantha Kumar、Prabudha Basu、L. Adhikary、M. J. Nanjan

  DOI：10.1080/00397911.2011.576322

  日期：2012.10.15

  We report facile and efficient conversion of the amino functional group of amino acids such a s L-tyrosine, DL-phenylalanine, and glycine to the corresponding (+/-)-2-t-hioxo-thiazolidine-4-ones (rhodanines). Stereospecific synthesis of amino acid-incorporated rhodanine is achieved in the case of L-tyrosine. Knoevenagel condensation over the active methylene group at the fifth position of the corresponding rhodanines is also described. The substituted rhodanine incorporated with tyrosine in the form of a dimer connected via two-carbon linker possesses significant anticancer activity against A549 cells (human lung cancer cells).