1-Ethyl-3-(3'.4'-dichlorphenyl)-thioharnstoff | 27020-72-0

• 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-Ethyl-3-(3'.4'-dichlorphenyl)-thioharnstoff
• 英文别名: 1-(3,4-dichlorophenyl)-3-ethylthiourea
• CAS: 27020-72-0
• 化学式: C₉H₁₀Cl₂N₂S
• mdl: MFCD02320805
• 分子量: 249.164
• InChiKey: KULSKCPLQVVZPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Ethyl-3-(3'.4'-dichlorphenyl)-thioharnstoff 在 potassium carbonate 作用下， 以 丙醇 、 丙酮 为溶剂， 生成 N-(ethyl)-N'-(3,4-dichlorophenyl)-N''-(1-isopropyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)guanidine
  参考文献：
  名称：

  Synthesis and Antimalarial Activity of 2-Guanidino-4-oxoimidazoline Derivatives

  摘要：

  A series of 2-guanidino-4-oxoimidazoline (deoxo-IZ) derivatives was prepared and showed potent antimalarial activities in rodent and Rhesus models. Compound 8e, the most potent analogues of this series, is the first non-8-aminoqinoline antimalarial that demonstrated radical curative activity in non-human primate by Cl oral route and showed causal prophylactic activity comparable to that of the commonly used clinical drugs in Rhesus monkeys infected with sporozoites of Plasmodium cynomolgi. The metabolic stability and metabolites profile indicated that the new deoxo-IZ derivatives (8) may act as prodrugs of the corresponding IZ (1 and 2) derivatives.

  DOI：

  10.1021/jm200111g
• 作为产物：
  描述：

  乙胺 、 3,4-二氯异硫氰酸苯酯 以 二氯甲烷 为溶剂， 以87%的产率得到1-Ethyl-3-(3'.4'-dichlorphenyl)-thioharnstoff
  参考文献：
  名称：

  Synthesis and Antimalarial Activity of 2-Guanidino-4-oxoimidazoline Derivatives

  摘要：

  A series of 2-guanidino-4-oxoimidazoline (deoxo-IZ) derivatives was prepared and showed potent antimalarial activities in rodent and Rhesus models. Compound 8e, the most potent analogues of this series, is the first non-8-aminoqinoline antimalarial that demonstrated radical curative activity in non-human primate by Cl oral route and showed causal prophylactic activity comparable to that of the commonly used clinical drugs in Rhesus monkeys infected with sporozoites of Plasmodium cynomolgi. The metabolic stability and metabolites profile indicated that the new deoxo-IZ derivatives (8) may act as prodrugs of the corresponding IZ (1 and 2) derivatives.

  DOI：

  10.1021/jm200111g

文献信息

• [EN] 2-GUANIDINO-4-OXO-IMIDAZOLINE DERIVATIVES AS ANTIMALARIAL AGENTS, SYNTHESIS AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE 2-GUANIDINO-4-OXO-IMIDAZOLINE EN TANT QU'AGENTS ANTIPALUDIQUES, SYNTHÈSE ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：US OF AMERICA AS REPRESENTED BY THE SECRETARY OF ARMY

  公开号：WO2012149093A1

  公开（公告）日：2012-11-01

  The present invention relates to new 2-guanidino-4-oxo-imidazoline derivatives (deoxo-IZ), methods of making these compounds, compositions containing the same, and methods of using the same to prevent, treat, or inhibit malaria in a subject.

  本发明涉及新的2-胍基-4-氧代-咪唑啉衍生物（deoxo-IZ），制备这些化合物的方法，含有这些化合物的组合物，以及利用这些化合物预防、治疗或抑制受试者体内疟疾的方法。
• Synthesis and antimicrobial evaluation of new halogenated 1,3-Thiazolidin-4-ones
  作者：Shaymaa G. Hammad、Marwa G. El-Gazzar、Nader S. Abutaleb、Daoyi Li、Isabell Ramming、Aditya Shekhar、Mohammad Abdel-Halim、Eman Z. Elrazaz、Mohamed N. Seleem、Ursula Bilitewski、Khaled A.M. Abouzid、Ebaa M. El-Hossary

  DOI：10.1016/j.bioorg.2019.103517

  日期：2020.1

  ongoing prevalence of multidrug-resistant bacterial pathogens requires the development of new effective antibacterial agents. In this study, two series of halogenated 1,3-thiazolidin-4-ones were synthesized and characterized. All the synthesized thiazolidinone derivatives were evaluated for their antimicrobial activity. Biological screening of the tested compounds revealed the antibacterial activity

  耐多药细菌性病原体的持续流行要求开发新的有效抗菌剂。在这项研究中，合成和表征了两个系列的卤代1,3-噻唑烷酮-4-酮。评价所有合成的噻唑烷酮衍生物的抗微生物活性。对被测化合物的生物学筛选显示，氯化噻唑烷酮4a，4b和4c对大肠杆菌TolC突变体具有抗菌活性，MIC值为16 µg / mL。亚抑制浓度的大肠菌素（0.25×MIC）与化合物4a，4b或4c的组合显示出对不同革兰氏阴性细菌（MICs = 4-16 µg / mL）的抗菌活性。有趣的是，化合物4a，4b和4c对鼠成纤维细胞和Caco-2细胞没有细胞毒性。氯化噻唑烷酮衍生物16d对一组致病性革兰氏阳性细菌具有抑菌活性，包括临床分离的甲氧西林和耐万古霉素的金黄色葡萄球菌，李斯特菌和多药耐药的表皮葡萄球菌（MICs = 8-64 µg / mL），对Caco-2和L929细胞均无细胞毒性。在破坏预先形成的MRSA生物膜方面，化合物16d
• Synthesis and Antimalarial Activity of 2-Guanidino-4-oxoimidazoline Derivatives
  作者：Xianjun Liu、Xihong Wang、Qigui Li、Michael P. Kozar、Victor Melendez、Michael T. O’Neil、Ai J. Lin

  DOI：10.1021/jm200111g

  日期：2011.7.14

  A series of 2-guanidino-4-oxoimidazoline (deoxo-IZ) derivatives was prepared and showed potent antimalarial activities in rodent and Rhesus models. Compound 8e, the most potent analogues of this series, is the first non-8-aminoqinoline antimalarial that demonstrated radical curative activity in non-human primate by Cl oral route and showed causal prophylactic activity comparable to that of the commonly used clinical drugs in Rhesus monkeys infected with sporozoites of Plasmodium cynomolgi. The metabolic stability and metabolites profile indicated that the new deoxo-IZ derivatives (8) may act as prodrugs of the corresponding IZ (1 and 2) derivatives.