1-(4-methoxyphenyl)-3-[(5-methyl-1H-imidazole-4-carbonyl)amino]thiourea

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-methoxyphenyl)-3-[(5-methyl-1H-imidazole-4-carbonyl)amino]thiourea
• 化学式: C₁₃H₁₅N₅O₂S
• 分子量: 305.36
• InChiKey: JGRMYDWVMIAEQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-3-[(5-methyl-1H-imidazole-4-carbonyl)amino]thiourea 在 硫酸 作用下， 反应 2.0h， 以84%的产率得到N-(4-methoxyphenyl)-5-(5-methyl-1H-imidazole-4-yl)-1,3,4-thiadiazole-2-amine
  参考文献：
  名称：

  Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles

  摘要：

  In this work we reported the synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities in vitro of three new compound series obtained from ethyl(5-methyl-1-H-imidazole-4-carboxylate): acylthiosemicarbazide analogues 3a-d, 4-thiazolidinone analogues 4a-d and 1,3,4-thiadiazole analogues 5a-d. All synthesized compounds were characterized by IR, H-1, C-13 NMR and HRMS. The majority of the tested compounds show excellent anti-T gondii activity when compared to hydroxyurea and sulfadiazine. In addition it was also shown that most of the compounds in this study have a better performance against intracellular tachyzoites. The results for antimicrobial activity evaluation showed weak antibacterial and antifungal activities for all the tested molecules, when compared with the standard drugs (chloramphenicol and rifampicin for antibacterial activity; nistatin and ketoconazole for antifungal activity). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.017
• 作为产物：
  描述：

  (9ci)-5-甲基-1H-咪唑-4-羧酸肼 、 4-甲氧基苯基 异硫氰酸酯 以 乙醇 为溶剂， 生成 1-(4-methoxyphenyl)-3-[(5-methyl-1H-imidazole-4-carbonyl)amino]thiourea
  参考文献：
  名称：

  Imidazole-Thiosemicarbazide Derivatives as Potent Anti-Mycobacterium tuberculosis Compounds with Antibiofilm Activity

  摘要：

  结核分枝杆菌（Mtb）是一种细胞内病原菌，是结核病的病原体。这种疾病是最古老和最致命的细菌感染之一，因为它在全球范围内主要对低收入和中等收入国家构成了重大的健康、社会和经济挑战。缺乏有效的疫苗、长期昂贵的药物治疗和快速传播的耐药菌株导致结核病重新成为全球流行病。本研究评估了新的咪唑硫脲衍生物（ITDs）对Mtb感染的体外活性以及它们对分枝杆菌生物膜形成的影响。对新化合物在细胞系和人单核细胞源性巨噬细胞（MDMs）中的细胞毒性进行了研究。通过测定还原蓝的最小抑菌浓度、时间杀菌曲线、细菌细胞内生长和对生物膜形成的影响来评估ITDs的抗Mtb活性。进行了对ITDs耐药突变体的突变频率和全基因组测序。观察到具有穿透Mtb感染的人类巨噬细胞的能力、显著抑制结核杆菌细胞内生长和抑制Mtb生物膜形成的ITDs的抗分枝杆菌潜力。

  DOI：

  10.3390/cells10123476

文献信息

• Systematic Identification of Thiosemicarbazides for Inhibition of Toxoplasma gondii Growth In Vitro
  作者：Agata Paneth、Lidia Węglińska、Adrian Bekier、Edyta Stefaniszyn、Monika Wujec、Nazar Trotsko、Katarzyna Dzitko

  DOI：10.3390/molecules24030614

  日期：——

  One of the key stages in the development of new therapies in the treatment of toxoplasmosis is the identification of new non-toxic small molecules with high specificity to Toxoplasma gondii. In the search for such structures, thiosemicarbazide-based compounds have emerged as a novel and promising leads. Here, a series of imidazole-thiosemicarbazides with suitable properties for CNS penetration was

  开发治疗弓形虫病的新疗法的关键阶段之一是鉴定对弓形虫具有高度特异性的新型无毒小分子。在寻找这样的结构时，已经出现了基于硫代氨基脲的化合物，这是一种新颖且有前途的线索。在这里，评估了一系列具有适合CNS渗透的特性的咪唑-硫代氨基脲，以确定有效的抗弓形虫活性所需的结构要求。当与磺胺嘧啶相比对宿主细胞无毒时，最好的4-芳基硫代氨基脲3和4表现出更高的效能，表明它们的抗弓形虫活性具有很高的选择性。
• Inhibition of <i>Toxoplasma gondii</i> by 1,2,4-triazole-based compounds: marked improvement in selectivity relative to the standard therapy pyrimethamine and sulfadiazine
  作者：Lidia Węglińska、Adrian Bekier、Nazar Trotsko、Barbara Kaproń、Tomasz Plech、Katarzyna Dzitko、Agata Paneth

  DOI：10.1080/14756366.2022.2112576

  日期：2022.12.31
• Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles
  作者：André P. Liesen、Thiago M. de Aquino、Cristiane S. Carvalho、Vânia T. Lima、Janete M. de Araújo、José G. de Lima、Antônio R. de Faria、Edésio J.T. de Melo、Antonio J. Alves、Elias W. Alves、Anselmo Q. Alves、Alexandre J.S. Góes

  DOI：10.1016/j.ejmech.2010.05.017

  日期：2010.9

  In this work we reported the synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities in vitro of three new compound series obtained from ethyl(5-methyl-1-H-imidazole-4-carboxylate): acylthiosemicarbazide analogues 3a-d, 4-thiazolidinone analogues 4a-d and 1,3,4-thiadiazole analogues 5a-d. All synthesized compounds were characterized by IR, H-1, C-13 NMR and HRMS. The majority of the tested compounds show excellent anti-T gondii activity when compared to hydroxyurea and sulfadiazine. In addition it was also shown that most of the compounds in this study have a better performance against intracellular tachyzoites. The results for antimicrobial activity evaluation showed weak antibacterial and antifungal activities for all the tested molecules, when compared with the standard drugs (chloramphenicol and rifampicin for antibacterial activity; nistatin and ketoconazole for antifungal activity). (C) 2010 Elsevier Masson SAS. All rights reserved.
• Imidazole-Thiosemicarbazide Derivatives as Potent Anti-Mycobacterium tuberculosis Compounds with Antibiofilm Activity
  作者：Adrian Bekier、Malwina Kawka、Jakub Lach、Jarosław Dziadek、Agata Paneth、Justyna Gatkowska、Katarzyna Dzitko、Bożena Dziadek

  DOI：10.3390/cells10123476

  日期：——

  Mycobacterium tuberculosis (Mtb) is an intracellular pathogenic bacterium and the causative agent of tuberculosis. This disease is one of the most ancient and deadliest bacterial infections, as it poses major health, social and economic challenges at a global level, primarily in low- and middle-income countries. The lack of an effective vaccine, the long and expensive drug therapy, and the rapid spread of drug-resistant strains of Mtb have led to the re-emergence of tuberculosis as a global pandemic. Here, we assessed the in vitro activity of new imidazole-thiosemicarbazide derivatives (ITDs) against Mtb infection and their effects on mycobacterial biofilm formation. Cytotoxicity studies of the new compounds in cell lines and human monocyte-derived macrophages (MDMs) were performed. The anti-Mtb activity of ITDs was evaluated by determining minimal inhibitory concentrations of resazurin, time-kill curves, bacterial intracellular growth and the effect on biofilm formation. Mutation frequency and whole-genome sequencing of mutants that were resistant to ITDs were performed. The antimycobacterial potential of ITDs with the ability to penetrate Mtb-infected human macrophages and significantly inhibit the intracellular growth of tubercle bacilli and suppress Mtb biofilm formation was observed.

  结核分枝杆菌（Mtb）是一种细胞内病原菌，是结核病的病原体。这种疾病是最古老和最致命的细菌感染之一，因为它在全球范围内主要对低收入和中等收入国家构成了重大的健康、社会和经济挑战。缺乏有效的疫苗、长期昂贵的药物治疗和快速传播的耐药菌株导致结核病重新成为全球流行病。本研究评估了新的咪唑硫脲衍生物（ITDs）对Mtb感染的体外活性以及它们对分枝杆菌生物膜形成的影响。对新化合物在细胞系和人单核细胞源性巨噬细胞（MDMs）中的细胞毒性进行了研究。通过测定还原蓝的最小抑菌浓度、时间杀菌曲线、细菌细胞内生长和对生物膜形成的影响来评估ITDs的抗Mtb活性。进行了对ITDs耐药突变体的突变频率和全基因组测序。观察到具有穿透Mtb感染的人类巨噬细胞的能力、显著抑制结核杆菌细胞内生长和抑制Mtb生物膜形成的ITDs的抗分枝杆菌潜力。