5-(3-cyanophenyl)-3-(4-cyanopyridin-2-yl)isoxazole | 1531598-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(3-cyanophenyl)-3-(4-cyanopyridin-2-yl)isoxazole
• CAS: 1531598-74-9
• 化学式: C₁₆H₈N₄O
• 分子量: 272.266
• InChiKey: BWHRUIFHRLLCPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C (decomp)
• 沸点：
  516.7±50.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.5
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(3-cyanophenyl)-3-(4-cyanopyridin-2-yl)isoxazole 在 盐酸 、 palladium 10% on activated carbon 、 盐酸羟胺 、 potassium tert-butylate 、 氢气 作用下， 以 水 、 溶剂黄146 、 二甲基亚砜 为溶剂， 25.0 ℃ 、413.7 kPa 条件下， 反应 4.0h， 生成 5-(3-amidinophenyl)-3-(4-amidinopyridin-2-yl)isoxazole trihydrochloride
  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：

  2-羟基甲基-4-吡啶甲腈 在 manganese(IV) oxide 、 N-氯代丁二酰亚胺 、 盐酸羟胺 、 三丁基氧化锡 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(3-cyanophenyl)-3-(4-cyanopyridin-2-yl)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