(S)-4-methyl-2-(4-oxo-2-thioxothiazolidin-3-yl)pentanoic acid | 932388-83-5

• 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)-4-methyl-2-(4-oxo-2-thioxothiazolidin-3-yl)pentanoic acid
• 英文别名: (2S)-4-methyl-2-(4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl)pentanoic acid
• CAS: 932388-83-5
• 化学式: C₉H₁₃NO₃S₂
• 分子量: 247.339
• InChiKey: SXQSBDRUPMQHSD-LURJTMIESA-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：

  (S)-4-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， 生成 2-((Z)-5-(4-((E)-(2-(1-naphthoyl)hydrazono)methyl)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-4-methylpentanoic acid
  参考文献：
  名称：

  Novel arylhydrazone derivatives bearing a rhodanine moiety: synthesis and evaluation of their antibacterial activities

  摘要：

  一系列含有绕丹宁基团的苯腙衍生物已被合成、表征并评估为抗菌剂。其中一些化合物显示出对多种不同革兰氏阳性菌株的强效抗菌活性，包括多药耐药的临床分离株。在测试的化合物中，IIk和IIIk被认定为最有效，对包括甲氧西林耐药和喹诺酮耐药的金黄色葡萄球菌在内的多药耐药革兰氏阳性菌的最低抑制浓度值为2-4 μg/mL。这些化合物在64 μg/mL的浓度下对革兰氏阴性菌大肠杆菌1356均未表现出任何活性。

  DOI：

  10.1007/s12272-013-0214-3
• 作为产物：
  描述：

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

  Novel arylhydrazone derivatives bearing a rhodanine moiety: synthesis and evaluation of their antibacterial activities

  摘要：

  一系列含有绕丹宁基团的苯腙衍生物已被合成、表征并评估为抗菌剂。其中一些化合物显示出对多种不同革兰氏阳性菌株的强效抗菌活性，包括多药耐药的临床分离株。在测试的化合物中，IIk和IIIk被认定为最有效，对包括甲氧西林耐药和喹诺酮耐药的金黄色葡萄球菌在内的多药耐药革兰氏阳性菌的最低抑制浓度值为2-4 μg/mL。这些化合物在64 μg/mL的浓度下对革兰氏阴性菌大肠杆菌1356均未表现出任何活性。

  DOI：

  10.1007/s12272-013-0214-3

文献信息

• In Silico Driven Design and Synthesis of Rhodanine Derivatives as Novel Antibacterials Targeting the Enoyl Reductase InhA
  作者：Liudas Slepikas、Gianpaolo Chiriano、Remo Perozzo、Sébastien Tardy、Agata Kranjc、Ophélie Patthey-Vuadens、Hajer Ouertatani-Sakouhi、Sébastien Kicka、Christopher F. Harrison、Tiziana Scrignari、Karl Perron、Hubert Hilbi、Thierry Soldati、Pierre Cosson、Eduardas Tarasevicius、Leonardo Scapozza

  DOI：10.1021/acs.jmedchem.5b01620

  日期：2016.12.22

  computational studies. Their antimicrobial activity was assessed against Mycobacterium marinum (Mm) (a model for Mtb), Pseudomonas aeruginosa (Pa), Legionella pneumophila (Lp), and Enterococcus faecalis (Ef) by using anti-infective, antivirulence, and antibiotic assays. Nineteen out of 34 compounds reduced Mm virulence at 10 μM. 33 exhibited promising antibiotic activity against Mm with a MIC of 0.21 μM and showed

  在这里，我们报告针对结核分枝杆菌结核（Mtb）反-2-烯酰基酰基载体蛋白还原酶（InhA）的4-噻唑烷酮（若丹宁）衍生物的设计，合成和生物学评估。在罗丹宁环第5位具有庞大芳族取代基且在N -3位具有色氨酸残基的化合物对InhA的活性最高，IC 50值为2.7至30μM。实验数据显示与计算研究一致的相关性。他们的抗菌活性评估了对结核分枝杆菌（Mm）（铜绿假单胞菌（Mtb）的模型）。Pa），嗜肺军团菌（Lp）和粪肠球菌（Ef），方法是使用抗感染，抗毒力和抗生素检测方法。34种化合物中有19种降低了10μM的Mm毒力。33的MIC为0.21μM，对Mm表现出有希望的抗生素活性，在30μM的抗感染试验中，Lp的生长降低了89％。32显示对Ef的高抗生素活性，MIC为0.57μM。
• [EN] BIARYLRHODANINE AND PYRIDYLRHODANINE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS DE BIARYLRHODANINE ET DE PYRIDYLRHODANINE ET LEUR UTILISATION
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2010024783A1

  公开（公告）日：2010-03-04

  The present invention pertains generally to the field of therapeutic compounds, and more specifically to compounds related to rhodanine, which compounds are inter alia inhibitors and/or binders of antiapoptotic/pro-survival Bcl-2 proteins such as Bcl-XL and/or Mcl-1. More specifically, the present invention is concerned with Rhodanine- based Pan-Bcl-2 inhibitors and Mcl-1 -specific inhibitors as anti-cancer compounds. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit and/or bind Bcl-2 proteins such as Bcl-XL and/or Mcl-1, and in the treatment of diseases and conditions that are mediated by Bcl-2 proteins, that are ameliorated by the inhibition of Bcl-2 protein function (such as Bcl-XL and/or Mcl-1 ) including proliferative conditions such as cancer, optionally in combination with another agent.

  本发明一般涉及治疗化合物领域，更具体地涉及与罗丹宁相关的化合物，这些化合物是抑制剂和/或结合剂，用于抑制和/或结合抗凋亡/促存活的Bcl-2蛋白，如Bcl-XL和/或Mcl-1。更具体地，本发明涉及基于罗丹宁的Pan-Bcl-2抑制剂和Mcl-1特异性抑制剂作为抗癌化合物。本发明还涉及包括这些化合物的药物组合物，以及在体外和体内使用这些化合物和组合物来抑制和/或结合Bcl-2蛋白，如Bcl-XL和/或Mcl-1，并用于治疗由Bcl-2蛋白介导的疾病和症状，通过抑制Bcl-2蛋白功能（如Bcl-XL和/或Mcl-1）改善的疾病和症状，包括增殖性疾病如癌症，可选择地与另一药剂联合使用。
• 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 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 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.