3-(3-溴-4,5-二甲氧基-苯基)-5-氯-1,3-二氢-异苯并呋喃-1-醇 | 1026063-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3-溴-4,5-二甲氧基-苯基)-5-氯-1,3-二氢-异苯并呋喃-1-醇
• 英文名称: 3-(3-Bromo-4,5-dimethoxyphenyl)-5-chloro-1,3-dihydro-2-benzofuran-1-ol
• CAS: 1026063-35-3
• 化学式: C₁₆H₁₄BrClO₄
• 分子量: 385.642
• InChiKey: MLBQOPQZRXDALF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-溴-4,5-二甲氧基-苯基)-5-氯-1,3-二氢-异苯并呋喃-1-醇 在 sodium hydroxide 、 三氟化硼乙醚 、 溶剂黄146 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 8.5h， 生成 1-(3-Bromo-4,5-dimethoxy-phenyl)-7-chloro-3-[4-(2-hydroxy-ethyl)-piperazine-1-carbonyl]-naphthalene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  1-Arylnaphthalene Lignan:  A Novel Scaffold for Type 5 Phosphodiesterase Inhibitor

  摘要：

  1-Arylnaphthalene lignan, which had been reported as a PDE4 inhibitor by Iwasaki, was disclosed as a new structural class of PDE5 inhibitors. The structural requirements for potent and specific PDE5 inhibition were revealed in a 1-arylnaphthalene lignan series, in which 1-(3-bromo-4, 5-dimethoxyphenyl)-5-chloro-3-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-2-(methoxycarbonyl)naphthalene hydrochloride (27q) showed the most potent and specific inhibition (PDE5 inhibition IC50 = 6.2 nM, selectivity for PDE5 against PDE1, -2, -3, and -4 > 16 000). It is noteworthy that 27q has the best selectivities against PDE isoforms among PDE5 inhibitors so far reported. Compound 27q exhibited almost the same relaxant effects on rat aortic rings as sodium 1-[6-chloro-4-[(3,4-methylenedioxybenzyl)amino]quinazolin-2-yl]piperidine-4-carboxylate (35) (27q, EC50 = 0.10 mu M; 35, EC50 = 0.20 mu M) and was selected for further biological evaluation.

  DOI：

  10.1021/jm9807048
• 作为产物：
  描述：

  3-溴-4,5-二甲氧基苯甲醛 在 盐酸 、 四甲基乙二胺 、 仲丁基锂 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 3-(3-溴-4,5-二甲氧基-苯基)-5-氯-1,3-二氢-异苯并呋喃-1-醇
  参考文献：
  名称：

  1-Arylnaphthalene Lignan:  A Novel Scaffold for Type 5 Phosphodiesterase Inhibitor

  摘要：

  1-Arylnaphthalene lignan, which had been reported as a PDE4 inhibitor by Iwasaki, was disclosed as a new structural class of PDE5 inhibitors. The structural requirements for potent and specific PDE5 inhibition were revealed in a 1-arylnaphthalene lignan series, in which 1-(3-bromo-4, 5-dimethoxyphenyl)-5-chloro-3-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-2-(methoxycarbonyl)naphthalene hydrochloride (27q) showed the most potent and specific inhibition (PDE5 inhibition IC50 = 6.2 nM, selectivity for PDE5 against PDE1, -2, -3, and -4 > 16 000). It is noteworthy that 27q has the best selectivities against PDE isoforms among PDE5 inhibitors so far reported. Compound 27q exhibited almost the same relaxant effects on rat aortic rings as sodium 1-[6-chloro-4-[(3,4-methylenedioxybenzyl)amino]quinazolin-2-yl]piperidine-4-carboxylate (35) (27q, EC50 = 0.10 mu M; 35, EC50 = 0.20 mu M) and was selected for further biological evaluation.

  DOI：

  10.1021/jm9807048