1-[(5-methyl-1H-imidazole-4-yl)carbonyl]-4-phenylthiosemicarbazide | 349629-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[(5-methyl-1H-imidazole-4-yl)carbonyl]-4-phenylthiosemicarbazide
• 英文别名: 1-[(5-methyl-1H-imidazole-4-carbonyl)amino]-3-phenylthiourea
• CAS: 349629-96-5
• 化学式: C₁₂H₁₃N₅OS
• 分子量: 275.334
• InChiKey: DTQSNQAVMYCORR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(5-methyl-1H-imidazole-4-yl)carbonyl]-4-phenylthiosemicarbazide 在 硫酸 作用下， 反应 2.0h， 以93%的产率得到N-phenyl-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：

  硫代异氰酸苯酯 、 (9ci)-5-甲基-1H-咪唑-4-羧酸肼 以 乙醚 为溶剂， 反应 12.0h， 以62%的产率得到1-[(5-methyl-1H-imidazole-4-yl)carbonyl]-4-phenylthiosemicarbazide
  参考文献：
  名称：

  1-唑啉-4-芳基/烷基-氨基硫脲环化方向的研究

  摘要：

  对四个系列的1-唑啉-4-芳基/烷基-氨基硫脲进行了唑基对分子内环化能力的影响及其方向的研究。发现对于在 N-1 个氮原子上具有三唑、咪唑或吡咯部分的 4-芳基/烷基-氨基硫脲，在碱性和酸性介质中，可能的产物仅为 s-三唑。仅针对一系列 1-(4-甲基-1,2,3-噻二唑-5-基-羰基)-4- 1-唑基-4-芳基/烷基-氨基硫脲成功脱氢环化生成噻二唑芳基/烷基氨基硫脲。可以推测，1-唑啉-4-芳基/烷基-氨基硫脲的氧原子pKa值的测定可能是预测脱氢环化形成噻二唑的可能性的非常有价值的参数。© 2010 威利期刊公司。杂原子化学 21:521–532, 2010; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20643

  DOI：

  10.1002/hc.20643

文献信息

• Study of direction of cyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides
  作者：Agata Siwek、Monika Wujec、Maria Dobosz、Irena Wawrzycka-Gorczyca

  DOI：10.1002/hc.20643

  日期：——

  , a study on the influence of azole moiety on the capability for intramolecular cyclization and its direction was carried out. It was found that for 4-aryl/alkyl-thiosemicabazides with triazole, imidazole, or pyrrole moiety at N-1 nitrogen atom possible products were only s-triazoles, both in alkaline and acidic medium. Successful dehydrocyclization of 1-azolil-4-aryl/alkyl-thiosemicarbazides leading

  对四个系列的1-唑啉-4-芳基/烷基-氨基硫脲进行了唑基对分子内环化能力的影响及其方向的研究。发现对于在 N-1 个氮原子上具有三唑、咪唑或吡咯部分的 4-芳基/烷基-氨基硫脲，在碱性和酸性介质中，可能的产物仅为 s-三唑。仅针对一系列 1-(4-甲基-1,2,3-噻二唑-5-基-羰基)-4- 1-唑基-4-芳基/烷基-氨基硫脲成功脱氢环化生成噻二唑芳基/烷基氨基硫脲。可以推测，1-唑啉-4-芳基/烷基-氨基硫脲的氧原子pKa值的测定可能是预测脱氢环化形成噻二唑的可能性的非常有价值的参数。© 2010 威利期刊公司。杂原子化学 21:521–532, 2010; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20643
• 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.