7-bromo-2-hydroxymethyl-3,4-dihydronaphthalene | 914262-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-bromo-2-hydroxymethyl-3,4-dihydronaphthalene
• 英文别名: (7-Bromo-3,4-dihydronaphthalen-2-yl)methanol
• CAS: 914262-76-3
• 化学式: C₁₁H₁₁BrO
• 分子量: 239.112
• InChiKey: DPBNDVQANZVZOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  92 °C(Solv: heptane (142-82-5))
• 沸点：
  340.5±42.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-bromo-2-hydroxymethyl-3,4-dihydronaphthalene 在 四(三苯基膦)钯 manganese(IV) oxide 、 氨 、 potassium acetate 、 magnesium sulfate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 3.0h， 生成 2-(2-cyano-3,4-dihydronaphthalen-7-yl)-5-(4-cyanophenyl)furan
  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：

  3-(4-溴苯甲酰)丙酸 在 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 PPA 、 水 、 sodium hydride 、 silver nitrate 、 肼 作用下， 以 1,4-二氧六环 、 乙醇 、 丙酮 、 苯 、 三乙二醇 为溶剂， 反应 7.83h， 生成 7-bromo-2-hydroxymethyl-3,4-dihydronaphthalene
  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