methyl 4-ethyl-3-[2-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoate | 165801-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑二氮卓类
• 英文名称: methyl 4-ethyl-3-[2-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoate
• CAS: 165801-70-7
• 化学式: C₁₈H₂₂N₄O₃
• 分子量: 342.398
• InChiKey: ILMQKJVGWDZAFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-ethyl-3-[2-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-ethyl-3-[2-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoic acid
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues

  摘要：

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.

  DOI：

  10.1021/jm990448e
• 作为产物：
  描述：

  4-羟基-3-丙-2-烯基苯甲酸甲酯 在 10percent Pd/C 咪唑 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 四溴化碳 、 camphor-10-sulfonic acid 、 氢气 、 sodium hydride 、 臭氧 、 三乙胺 、 三苯基膦 、 sodium iodide 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -78.0~90.0 ℃ 、206.85 kPa 条件下， 反应 59.58h， 生成 methyl 4-ethyl-3-[2-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoate
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues

  摘要：

  N3-Substituted coformycin aglycon analogues with improved AMP deaminase (AMPDA) inhibitory potency are described. Replacement of the 5-carboxypentyl substituent in the lead AMPDA inhibitor 3-(5-carboxypentyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (2) described in the previous article with various carboxyarylalkyl groups resulted in compounds with 10-100-fold improved AMPDA inhibitory potencies. The optimal N3 substituent had m-carboxyphenyl with a two-carbon alkyl tether. For example, 3-[2-(3-carboxy-5-ethylphenyl)-ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d] [1,3]diazepin-8-ol (43g) inhibited human AMPDA with a K-i = 0.06 mu M. The compounds within the series also exhibited >1000-fold specificity for AMPDA relative to adenosine deaminase.

  DOI：

  10.1021/jm990448e