5-[(1R)-2-[benzyl-(4,5,6,7-tetramethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-phenylmethoxy-1H-quinolin-2-one | 312754-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-[(1R)-2-[benzyl-(4,5,6,7-tetramethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-phenylmethoxy-1H-quinolin-2-one
• CAS: 312754-35-1
• 化学式: C₃₈H₄₀N₂O₃
• 分子量: 572.747
• InChiKey: ORKGJCBHPKCJBA-DHUJRADRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(1R)-2-[benzyl-(4,5,6,7-tetramethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-phenylmethoxy-1H-quinolin-2-one 在 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 8-hydroxy-5-[(1R)-1-hydroxy-2-[(4,5,6,7-tetramethyl-2,3-dihydro-1H-inden-2-yl)amino]ethyl]-1H-quinolin-2-one
  参考文献：
  名称：

  An investigation into the structure–activity relationships associated with the systematic modification of the β2-adrenoceptor agonist indacaterol

  摘要：

  The synthesis of a series of indacaterol analogues in which each of the three structural regions of indacaterol are modified in a systematic manner is described. Evaluation of the affinity of these analogues for the beta(2)-adrenoceptor identified the 3,4-dihydroquinolinone and 5-n-butylindanyl analogues to demonstrate the most similar profiles to indacaterol. An alpha-methyl aminoindane analogue was discovered to be 25-fold more potent than indacaterol, and functional studies revealed an atypical beta(2)-adrenoceptor activation profile for this compound consistent with that of a slowly dissociating 'super agonist'. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.096
• 作为产物：
  描述：

  四甲基萘 在 盐酸 、 aluminum (III) chloride 、 sodium tetrahydroborate 、 亚硝酸异丁酯 、 硫酸 、 10% Pd/C 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 、 氯仿 、 正丁醇 为溶剂， 25.0~110.0 ℃ 、303.99 kPa 条件下， 反应 68.5h， 生成 5-[(1R)-2-[benzyl-(4,5,6,7-tetramethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-phenylmethoxy-1H-quinolin-2-one
  参考文献：
  名称：

  An investigation into the structure–activity relationships associated with the systematic modification of the β2-adrenoceptor agonist indacaterol

  摘要：

  The synthesis of a series of indacaterol analogues in which each of the three structural regions of indacaterol are modified in a systematic manner is described. Evaluation of the affinity of these analogues for the beta(2)-adrenoceptor identified the 3,4-dihydroquinolinone and 5-n-butylindanyl analogues to demonstrate the most similar profiles to indacaterol. An alpha-methyl aminoindane analogue was discovered to be 25-fold more potent than indacaterol, and functional studies revealed an atypical beta(2)-adrenoceptor activation profile for this compound consistent with that of a slowly dissociating 'super agonist'. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.096