7-(4-bromophenyl)-2-cyanonaphthalene | 914262-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-(4-bromophenyl)-2-cyanonaphthalene
• CAS: 914262-90-1
• 化学式: C₁₇H₁₀BrN
• 分子量: 308.177
• InChiKey: GCBXXCHWVCSDQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  7-(4-bromophenyl)-2-cyanonaphthalene 在 palladium diacetate 盐酸羟胺 、 potassium tert-butylate 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 7-(4'-N-hydroxyamidinobiphenyl-4-yl)-2-N-hydroxyamidinonaphthalene
  参考文献：
  名称：

  Dicationic DNA-targeted antiprotozoal agents: Naphthalene replacement of benzimidazole

  摘要：

  A series of naphthalene analogues of highly active benzimidazole diamidines were synthesized using sequential Stille and Suzuki coupling reactions for preparation of the bis-nitrile intermediates. All of the diamidines showed strong DNA affinities as judged by high Delta T-m values with poly(dA-dT). The dicationic compounds were quite active in vitro versus Trypanosoma brucei rhodesiense (T. b. r.) exhibiting IC50 values ranging from 4 to 98 nM. These compounds were also active versus Plasmodium falciparum (P. f) giving IC50 values ranging from 4 to 33 nM. Two of the compounds showed good activity in vivo in the STIB900 model for acute African trypanosomiasis; one gave 3/4 cures and the other gave 4/4 cures on ip dosage of 20 mg/kg for 4 days. The amidoxime prodrugs of the naphthalene analogues were essentially ineffective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.024
• 作为产物：
  描述：

  7-甲氧基-2-萘 在 四(三苯基膦)钯 、 palladium diacetate 吡啶 、 四丁基氟化铵 、 三溴化硼 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 56.0h， 生成 7-(4-bromophenyl)-2-cyanonaphthalene
  参考文献：
  名称：

  Dicationic DNA-targeted antiprotozoal agents: Naphthalene replacement of benzimidazole

  摘要：

  A series of naphthalene analogues of highly active benzimidazole diamidines were synthesized using sequential Stille and Suzuki coupling reactions for preparation of the bis-nitrile intermediates. All of the diamidines showed strong DNA affinities as judged by high Delta T-m values with poly(dA-dT). The dicationic compounds were quite active in vitro versus Trypanosoma brucei rhodesiense (T. b. r.) exhibiting IC50 values ranging from 4 to 98 nM. These compounds were also active versus Plasmodium falciparum (P. f) giving IC50 values ranging from 4 to 33 nM. Two of the compounds showed good activity in vivo in the STIB900 model for acute African trypanosomiasis; one gave 3/4 cures and the other gave 4/4 cures on ip dosage of 20 mg/kg for 4 days. The amidoxime prodrugs of the naphthalene analogues were essentially ineffective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.024