Ethyl 3-methoxy-4-[2-(8-oxo-4,7-dihydroimidazo[4,5-d][1,3]diazepin-3-yl)ethyl]-5,6,7,8-tetrahydronaphthalene-2-carboxylate | 331282-30-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Ethyl 3-methoxy-4-[2-(8-oxo-4,7-dihydroimidazo[4,5-d][1,3]diazepin-3-yl)ethyl]-5,6,7,8-tetrahydronaphthalene-2-carboxylate
• CAS: 331282-30-5
• 化学式: C₂₂H₂₆N₄O₄
• 分子量: 410.473
• InChiKey: YMPHTQQDZITVEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 3-methoxy-4-[2-(8-oxo-4,7-dihydroimidazo[4,5-d][1,3]diazepin-3-yl)ethyl]-5,6,7,8-tetrahydronaphthalene-2-carboxylate 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 生成 4-[2-(8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-3-methoxy-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 5. Design, Synthesis, and SAR of a Highly Potent Inhibitor Series

  摘要：

  A highly potent AMP deaminase (AMPDA) inhibitor series was discovered by replacing the N3 substitutents of the two lead AMPDA inhibitor series with a conformationally restricted group. The most potent compound, 3-[2-(3-carboxy-4-bromo-5,6,7,8-tetrahydroaphthyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (24b), represents a 10- to 250-fold enhancement in AMPDA inhibitory potency without loss in the enzyme specificity. The potency of the inhibitor 24b (AMPDA K-i = 0.002 muM) is 10(5)-fold lower than the K-m for the substrate AMP. It represents the most potent nonnucleotide AMPDA inhibitor known.

  DOI：

  10.1021/jm000355t
• 作为产物：
  描述：

  乙基3-羟基-2-萘甲酸酯 在 20percent Pd(OH)2/C 9-borabicyclo[3.3.1]nonane dimer 、 四(三苯基膦)钯 、 四溴化碳 、 氢气 、 溴 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 5.0~80.0 ℃ 、101.33 kPa 条件下， 反应 74.5h， 生成 Ethyl 3-methoxy-4-[2-(8-oxo-4,7-dihydroimidazo[4,5-d][1,3]diazepin-3-yl)ethyl]-5,6,7,8-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  AMP Deaminase Inhibitors. 5. Design, Synthesis, and SAR of a Highly Potent Inhibitor Series

  摘要：

  A highly potent AMP deaminase (AMPDA) inhibitor series was discovered by replacing the N3 substitutents of the two lead AMPDA inhibitor series with a conformationally restricted group. The most potent compound, 3-[2-(3-carboxy-4-bromo-5,6,7,8-tetrahydroaphthyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (24b), represents a 10- to 250-fold enhancement in AMPDA inhibitory potency without loss in the enzyme specificity. The potency of the inhibitor 24b (AMPDA K-i = 0.002 muM) is 10(5)-fold lower than the K-m for the substrate AMP. It represents the most potent nonnucleotide AMPDA inhibitor known.

  DOI：

  10.1021/jm000355t

文献信息

• AMP Deaminase Inhibitors. 5. Design, Synthesis, and SAR of a Highly Potent Inhibitor Series
  作者：Srinivas Rao Kasibhatla、Brett C. Bookser、Wei Xiao、Mark D. Erion

  DOI：10.1021/jm000355t

  日期：2001.2.1

  A highly potent AMP deaminase (AMPDA) inhibitor series was discovered by replacing the N3 substitutents of the two lead AMPDA inhibitor series with a conformationally restricted group. The most potent compound, 3-[2-(3-carboxy-4-bromo-5,6,7,8-tetrahydroaphthyl)ethyl]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (24b), represents a 10- to 250-fold enhancement in AMPDA inhibitory potency without loss in the enzyme specificity. The potency of the inhibitor 24b (AMPDA K-i = 0.002 muM) is 10(5)-fold lower than the K-m for the substrate AMP. It represents the most potent nonnucleotide AMPDA inhibitor known.