1-(3,4-dichlorophenyl)-3-isopropyl thiourea | 74188-45-7

• 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-(3,4-dichlorophenyl)-3-isopropyl thiourea
• 英文别名: 1-(3,4-dichlorophenyl)-3-isopropylthiourea；1-(3,4-Dichlorophenyl)-3-propan-2-ylthiourea
• CAS: 74188-45-7
• 化学式: C₁₀H₁₂Cl₂N₂S
• mdl: MFCD06173590
• 分子量: 263.191
• InChiKey: GAXNJIRGEPBXQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-(3,4-dichlorophenyl)-3-isopropyl thiourea 在 potassium carbonate 作用下， 以 丙醇 、 丙酮 为溶剂， 生成 N-(3,4-dichlorophenyl)-N'-isopropyl-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：

  3,4-二氯异硫氰酸苯酯 、 异丙胺 以 二氯甲烷 为溶剂， 反应 18.0h， 以97%的产率得到1-(3,4-dichlorophenyl)-3-isopropyl thiourea
  参考文献：
  名称：

  [EN] 2-GUANIDINO-4-OXO-IMIDAZOLINE DERIVATIVES AS ANTIMALARIAL AGENTS, SYNTHESIS AND METHODS OF USE THEREOF
  [FR] DÉRIVÉS DE 2-GUANIDINO-4-OXO-IMIDAZOLINE EN TANT QU'AGENTS ANTIPALUDIQUES, SYNTHÈSE ET PROCÉDÉS D'UTILISATION DE CEUX-CI

  摘要：

  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。

  公开号：

  WO2012149093A1

文献信息

• Antimalarial Activities of New Guanidylimidazole and Guanidylimidazoline Derivatives
  作者：Liang Zhang、Ramadas Sathunuru、Diana Caridha、Brandon Pybus、Michael T. O’Neil、Michael P. Kozar、Ai J. Lin

  DOI：10.1021/jm200503s

  日期：2011.10.13

  A series of new guanidylimidazole derivatives was prepared and evaluated in mice and Rhesus monkeys infected with malarial sporozoites. The majority of the new compounds showed poor metabolic stability and weak in vitro activities in three clones of Plasmodium falciparum. Compounds 8a, 8h, 9a, 16a, and 16e cured the mice infected with sporozoites of P. berghei at 160 and 320 mg/kg/day x 3 po. Compounds 8a showed better causal prophylactic activity than primaquine, tafenoquine, and Malarone in the Rhesus test. In the radical curative test, 8a cured one monkey and delayed relapse of another for 74 days at 30 mg/kg/day x 7 by im. By oral dosing, 8a delayed relapse 81 days for one and 32 days for other vs 11-12 days for control monkeys treated with 10 mg/kg of chloroquine by po alone. Compound 8h, which showed superior activity to 8a in mouse test, delayed the relapse of treated monkeys for 21-26 days at 30 mg/kg/day x 7 by oral.
• [EN] GUANIDYLIMIDAZOLE AND GUANIDYLIMIDAZOLINE DERIVATIVES AS ANTIMALARIAL AGENTS, SYNTHESIS OF AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE GUANIDYLIMIDAZOLE ET DE GUANIDYLIMIDAZOLINE EN TANT QU'AGENTS ANTI-MALARIA, LEUR SYNTHÈSE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：US OF AMERICA AS REPRESENTED BY THE SECRETARY OF ARMY

  公开号：WO2012149097A2

  公开（公告）日：2012-11-01

  The present invention relates to new guanidylimidazole derivatives and guanidylimidazoline derivatives, methods of making these compounds, compositions containing the same, and methods of using the same to prevent, treat, or inhibit malaria in a subject.
• 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.
• [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。