Ethyl 3-bromo-5-[2-(8-oxo-4,7-dihydroimidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoate | 1026871-80-6

• 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: Ethyl 3-bromo-5-[2-(8-oxo-4,7-dihydroimidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoate
• CAS: 1026871-80-6
• 化学式: C₁₇H₁₇BrN₄O₃
• 分子量: 405.251
• InChiKey: UPRVSMXJFWQVLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 3-bromo-5-[2-(8-oxo-4,7-dihydroimidazo[4,5-d][1,3]diazepin-3-yl)ethyl]benzoate 在 sodium hydroxide 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 二乙二醇二甲醚 为溶剂， 反应 1.5h， 生成 3-(4-chlorophenyl)-5-[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：

  3,5-dibromobenzoic acid ethyl ester 在 ruthenium(IV) oxide 、 sodium tetrahydroborate 、 sodium periodate 、 四(三苯基膦)钯 、 四溴化碳 、 sodium hydride 、 三苯基膦 、 sodium iodide 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 37.75h， 生成 Ethyl 3-bromo-5-[2-(8-oxo-4,7-dihydroimidazo[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

文献信息

• AMP Deaminase Inhibitors. 3. SAR of 3-(Carboxyarylalkyl)coformycin Aglycon Analogues
  作者：Srinivas Rao Kasibhatla、Brett C. Bookser、Gary Probst、James R. Appleman、Mark D. Erion

  DOI：10.1021/jm990448e

  日期：2000.4.1

  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.