1-(3,4-dichlorophenyl)-3-(1H-imidazol-2-yl)thiourea | 1332704-18-3

• 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-(1H-imidazol-2-yl)thiourea
• CAS: 1332704-18-3
• 化学式: C₁₀H₈Cl₂N₄S
• 分子量: 287.172
• InChiKey: HUUPVNDXXGJFJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3,4-dichlorophenyl)-3-(1H-imidazol-2-yl)thiourea 在 氨 、 mercury dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以21%的产率得到N-(3,4-dichlorophenyl)-N'-(1H-imidazol-2-yl)guanidine hydrochloride
  参考文献：
  名称：

  Antimalarial Activities of New Guanidylimidazole and Guanidylimidazoline Derivatives

  摘要：

  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.

  DOI：

  10.1021/jm200503s
• 作为产物：
  描述：

  2-氨基咪唑 、 3,4-二氯异硫氰酸苯酯 以 二氯甲烷 为溶剂， 反应 18.0h， 以42%的产率得到1-(3,4-dichlorophenyl)-3-(1H-imidazol-2-yl)thiourea
  参考文献：
  名称：

  Antimalarial Activities of New Guanidylimidazole and Guanidylimidazoline Derivatives

  摘要：

  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.

  DOI：

  10.1021/jm200503s

文献信息

• [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.
• 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.