1,3-Dichloro-4-[2-(8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid benzyl ester | 331282-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3-Dichloro-4-[2-(8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid benzyl ester
• 英文别名: benzyl 1,3-dichloro-4-[2-(8-hydroxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl)ethyl]-5,6,7,8-tetrahydronaphthalene-2-carboxylate
• CAS: 331282-09-8
• 化学式: C₂₆H₂₆Cl₂N₄O₃
• 分子量: 513.423
• InChiKey: BTMGEDFAWKMHMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  1,3-Dichloro-4-[2-(8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid benzyl ester 在 10percent Pd/C 氢气 作用下， 以 甲醇 为溶剂， 反应 30.0h， 以46%的产率得到1,3-Dichloro-4-[2-(8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-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：

  5,6,7,8-tetrahydro-1-hydroxy-3-naphthoic acid 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium tetrahydroborate 、 磺酰氯 、 氢溴酸 、 sodium hydride 、 caesium carbonate 、 sodium iodide 、 lithium chloride 、 过氧化苯甲酰 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 1,3-Dichloro-4-[2-(8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid benzyl ester
  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