(2-二甲氧基甲基-4,5-二甲氧基-苯基)-(3-硝基-苯基)-甲醇 | 1025902-53-7

• 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: (2-二甲氧基甲基-4,5-二甲氧基-苯基)-(3-硝基-苯基)-甲醇
• 英文名称: [2-(Dimethoxymethyl)-4,5-dimethoxyphenyl]-(3-nitrophenyl)methanol
• CAS: 1025902-53-7
• 化学式: C₁₈H₂₁NO₇
• 分子量: 363.367
• InChiKey: WURHKJDQUSKBLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2-二甲氧基甲基-4,5-二甲氧基-苯基)-(3-硝基-苯基)-甲醇 在 sodium hydroxide 、 溶剂黄146 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 2.5h， 生成 3-[4-(2-Hydroxy-ethyl)-piperazine-1-carbonyl]-6,7-dimethoxy-1-(3-nitro-phenyl)-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：

  间硝基苯甲醛 、 1-溴-2-(二甲氧基甲基)-4,5-二甲氧基苯 在 三异丙氧基氯化钛 、 正丁基锂 作用下， 生成 (2-二甲氧基甲基-4,5-二甲氧基-苯基)-(3-硝基-苯基)-甲醇
  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