(2S)-3-methyl-2-(4-oxo-2-thioxothiazolidin-3-yl)pentanoic acid | 1440969-17-4

• 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
• 英文名称: (2S)-3-methyl-2-(4-oxo-2-thioxothiazolidin-3-yl)pentanoic acid
• 英文别名: (2S)-3-methyl-2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)pentanoic acid
• CAS: 1440969-17-4
• 化学式: C₉H₁₃NO₃S₂
• 分子量: 247.339
• InChiKey: NHJWCVZQPBQKPR-MSZQBOFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazole-2-carbaldehyde 、 (2S)-3-methyl-2-(4-oxo-2-thioxothiazolidin-3-yl)pentanoic acid 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以76%的产率得到(2S)-3-methyl-2-((Z)-5-((5-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-1H-imidazol-2-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)pentanoic acid
  参考文献：
  名称：

  含有喹喔啉基咪唑部分的手性罗丹宁衍生物作为 ALK5 抑制剂的合成和评价。

  摘要：

  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

  DOI：

  10.2174/1573406417666210628144849
• 作为产物：
  描述：

  二硫化碳 、 isoleucine 、 sodium monochloroacetic acid 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 生成 (2S)-3-methyl-2-(4-oxo-2-thioxothiazolidin-3-yl)pentanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of (E)-1-(substituted)-3-phenylprop-2-en-1-ones bearing rhodanines as potent anti-microbial agents

  摘要：

  Herein, we report the design, syntheses and in vitro anti-microbial activity of two series of rhodanines with chalcone moiety. Anti-microbial tests showed that some of the synthesized compounds exhibited good inhibition (MIC = 1-8 µg/mL) against multi-drug-resistant Gram-positive organisms, including methicillin resistant and quinolone-resistant Staphylococcus aureus, in which the compound 4g was found to be the most potent with minimum inhibitory concentration (MIC) value of 1 µg/mL against two methicillin-resistant S. aureus.

  DOI：

  10.3109/14756366.2013.837899

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 antibacterial evaluation of rhodanine-based 5-aryloxy pyrazoles against selected methicillin resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA)
  作者：Ming-Xia Song、Chang-Ji Zheng、Xian-Qing Deng、Liang-Peng Sun、Yan Wu、Lan Hong、Ying-Jing Li、Yi Liu、Zhi-Yu Wei、Ming-Jun Jin、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2012.12.007

  日期：2013.2

  With an intention to synergize the anti-bacterial activity of 5-aryloxy pyrazole and rhodanine derivatives, eight series of hybrid compounds have been synthesized and evaluated for their antibacterial activity. The majority of the synthesized compounds showed good inhibitory activity against selected methicillin resistant and quinolone-resistant Staphylococcus aureus (MRSA, QRSA) with minimum inhibitory concentration (MIC) values in the range of 1-32 mu g/mL. The cytotoxicity test suggests that these compounds exhibited in vitro antibacterial activity at non-cytotoxic concentrations. These studies therefore suggest that rhodanine-based 5-aryloxy pyrazoles are interesting scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety
  作者：Jian Che、Chang-Ji Zheng、Ming-Xia Song、Ya-Jing Bi、Yi Liu、Yin-Jing Li、Yan Wu、Liang-Peng Sun、Hu-Ri Piao

  DOI：10.1007/s00044-013-0648-7

  日期：2014.1

  Two series of furan derivatives bearing a rhodanine moiety (4a-l and 5a-l) have been synthesized, characterized, and evaluated for their antibacterial activity. The majority of these compounds showed potent levels of inhibitory activity against a variety of different Gram-positive bacteria, including multidrug-resistant clinical isolates, with minimum inhibitory concentration (MIC) values in the range of 2-16 mu g/mL. In particular, compound 4l was found to be the most potent of the synthesized compounds against the multidrug-resistant strains, with a MIC value of 2 or 4 mu g/mL. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. An examination of the cytotoxicities of these agents revealed that they displayed low levels of toxicity toward HeLa cells. All of the compounds synthesized in the current paper were characterized by H-1 and C-13 NMR, infrared, and mass spectroscopy.
• Synthesis and biological evaluation of rhodanine derivatives bearing a quinoline moiety as potent antimicrobial agents
  作者：Meng Guo、Chang-Ji Zheng、Ming-Xia Song、Yan Wu、Liang-Peng Sun、Yin-Jing Li、Yi Liu、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2013.05.082

  日期：2013.8

  Three series of rhodanine derivatives bearing a quinoline moiety (6a-h, 7a-g, and 8a-e) have been synthesized, characterized, and evaluated as antibacterial agents. The majority of these compounds showed potent antibacterial activities against several different strains of Gram-positive bacteria, including multidrug-resistant clinical isolates. Of the compounds tested, 6g and 8c were identified as the most effective with minimum inhibitory concentration (MIC) values of 1 mu g/mL against multidrug-resistant Gram-positive organisms, including methicillin-resistant and quinolone-resistant Staphylococcus aureus (MRSA and QRSA, respectively). None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. The cytotoxic activity assay showed that compounds 6g, 7g and 8e exhibited in vitro antibacterial activity at non-cytotoxic concentrations. Thus, these studies suggest that rhodanine derivatives bearing a quinoline moiety are interesting scaffolds for the development of novel Gram-positive antibacterial agents. (C) 2013 Elsevier Ltd. All rights reserved.