5-[4-(N'-hydroxy)amidinophenyl]-3-[4-(N'-hydroxy)amidino-2-methoxyphenyl]isoxazole | 1531598-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[4-(N'-hydroxy)amidinophenyl]-3-[4-(N'-hydroxy)amidino-2-methoxyphenyl]isoxazole
• 英文别名: N'-hydroxy-4-[5-[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]-1,2-oxazol-3-yl]-3-methoxybenzenecarboximidamide
• CAS: 1531598-91-0
• 化学式: C₁₈H₁₇N₅O₄
• 分子量: 367.364
• InChiKey: XVPVIVKACCHKNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  153
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[4-(N'-hydroxy)amidinophenyl]-3-[4-(N'-hydroxy)amidino-2-methoxyphenyl]isoxazole 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 以1.05 g的产率得到5-[4-(N'-hydroxy)amidinophenyl]-3-[4-(N'-hydroxy)amidino-2-methoxyphenyl]isoxazole dihydrochloride
  参考文献：
  名称：

  Antiprotozoal activity of dicationic 3,5-diphenylisoxazoles, their prodrugs and aza-analogues

  摘要：

  Fifty novel prodrugs and aza-analogues of 3,5-bis(4-amidinophenyl)isoxazole and its derivatives were prepared. Eighteen of the 24 aza-analogues exhibited IC50 values below 25 nM against Trypanosoma brucei rhodesiense or Plasmodium falciparum. Six compounds had antitrypanosomal IC50 values below 10 nM. Twelve analogues showed similar antiplasmodial activities, including three with sub-nanomolar potencies. Forty-four diamidines (including 16 aza-analogues) and the 26 prodrugs were evaluated for efficacy in mice infected with T. b. rhodesiense STIB900. Six diamidines cured 4/4 mice at daily 5 mg/kg intraperitoneal doses for 4 days, giving results far superior to pentamidine and furamidine. One prodrug attained 3/4 cures at daily 25 mg/kg oral doses for 4 days. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.10.050
• 作为产物：
  描述：

  3-(4-cyano-2-methoxyphenyl)-5-(4-cyanophenyl)isoxazole 在 盐酸羟胺 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以100%的产率得到5-[4-(N'-hydroxy)amidinophenyl]-3-[4-(N'-hydroxy)amidino-2-methoxyphenyl]isoxazole
  参考文献：
  名称：

  Antiprotozoal activity of dicationic 3,5-diphenylisoxazoles, their prodrugs and aza-analogues

  摘要：

  Fifty novel prodrugs and aza-analogues of 3,5-bis(4-amidinophenyl)isoxazole and its derivatives were prepared. Eighteen of the 24 aza-analogues exhibited IC50 values below 25 nM against Trypanosoma brucei rhodesiense or Plasmodium falciparum. Six compounds had antitrypanosomal IC50 values below 10 nM. Twelve analogues showed similar antiplasmodial activities, including three with sub-nanomolar potencies. Forty-four diamidines (including 16 aza-analogues) and the 26 prodrugs were evaluated for efficacy in mice infected with T. b. rhodesiense STIB900. Six diamidines cured 4/4 mice at daily 5 mg/kg intraperitoneal doses for 4 days, giving results far superior to pentamidine and furamidine. One prodrug attained 3/4 cures at daily 25 mg/kg oral doses for 4 days. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2013.10.050

文献信息

• Antiprotozoal activity of dicationic 3,5-diphenylisoxazoles, their prodrugs and aza-analogues
  作者：Donald A. Patrick、Stanislav A. Bakunov、Svetlana M. Bakunova、Tanja Wenzler、Reto Brun、Richard R. Tidwell

  DOI：10.1016/j.bmc.2013.10.050

  日期：2014.1

  Fifty novel prodrugs and aza-analogues of 3,5-bis(4-amidinophenyl)isoxazole and its derivatives were prepared. Eighteen of the 24 aza-analogues exhibited IC50 values below 25 nM against Trypanosoma brucei rhodesiense or Plasmodium falciparum. Six compounds had antitrypanosomal IC50 values below 10 nM. Twelve analogues showed similar antiplasmodial activities, including three with sub-nanomolar potencies. Forty-four diamidines (including 16 aza-analogues) and the 26 prodrugs were evaluated for efficacy in mice infected with T. b. rhodesiense STIB900. Six diamidines cured 4/4 mice at daily 5 mg/kg intraperitoneal doses for 4 days, giving results far superior to pentamidine and furamidine. One prodrug attained 3/4 cures at daily 25 mg/kg oral doses for 4 days. (C) 2013 Published by Elsevier Ltd.