8-(benzyloxy)-5-<2-<<1-(4-nitrophenyl)-2-methylprop-2-yl>amino>-1-hydroxyethyl>carbostyril | 128232-10-0

• 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: 8-(benzyloxy)-5-<2-<<1-(4-nitrophenyl)-2-methylprop-2-yl>amino>-1-hydroxyethyl>carbostyril
• 英文别名: 8-(benzyloxy)-5-(2-{[1-(4-nitrophenyl)-2-methylprop-2-yl]amino}-1-hydroxyethyl)carbostyril；5-[1-hydroxy-2-[[2-methyl-1-(4-nitrophenyl)propan-2-yl]amino]ethyl]-8-phenylmethoxy-1H-quinolin-2-one
• CAS: 128232-10-0
• 化学式: C₂₈H₂₉N₃O₅
• 分子量: 487.555
• InChiKey: BEIXZELPJQTZPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-(benzyloxy)-5-<2-<<1-(4-nitrophenyl)-2-methylprop-2-yl>amino>-1-hydroxyethyl>carbostyril 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.58h， 以33 mg的产率得到5-[2-[[1-(4-aminophenyl)-2-methylpropan-2-yl]amino]-1-hydroxyethyl]-8-hydroxy-1H-quinolin-2-one
  参考文献：
  名称：

  Carbostyril derivatives having potent .beta.-adrenergic agonist properties

  摘要：

  Derivatives carrying a substituent in the para position of the phenyl group of 8-hydroxy-5-[2-[(1-phenyl-2-methylprop-2-yl)amino]-1-hydroxyethyl] carbostyril (10) were prepared and their effects on beta-adrenoceptors evaluated in vitro. Unsubstituted compound 10, iodo 11, amino 12, and bromoacetamido 13 derivatives (all racemic) bound to the receptor with 15-100-fold lower dissociation constants than that of (-)-isoproterenol. All the above compounds stimulated adenylate cyclase more potently than (-)-isoproterenol. The intrinsic activities of compounds 10 and 12 were equal to that of (-)-isoproterenol. The intrinsic activities of compounds 11 and 13 were 1.3 and 1.2 times that of (-)-isoproterenol, respectively. Treatment of membrane preparations with bromoacetamido derivative 13 resulted in an irreversible loss of binding sites, and thus, 13 seems to be an alkylating affinity label for beta-adrenoceptors.

  DOI：

  10.1021/jm00392a006
• 作为产物：
  描述：

  (8-苯基甲氧基喹啉-5-基)甲醇 在 乙酸酐 、 sodium hydride 、 二甲基亚砜 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 28.0h， 生成 8-(benzyloxy)-5-<2-<<1-(4-nitrophenyl)-2-methylprop-2-yl>amino>-1-hydroxyethyl>carbostyril
  参考文献：
  名称：

  Carbostyril derivatives having potent .beta.-adrenergic agonist properties

  摘要：

  Derivatives carrying a substituent in the para position of the phenyl group of 8-hydroxy-5-[2-[(1-phenyl-2-methylprop-2-yl)amino]-1-hydroxyethyl] carbostyril (10) were prepared and their effects on beta-adrenoceptors evaluated in vitro. Unsubstituted compound 10, iodo 11, amino 12, and bromoacetamido 13 derivatives (all racemic) bound to the receptor with 15-100-fold lower dissociation constants than that of (-)-isoproterenol. All the above compounds stimulated adenylate cyclase more potently than (-)-isoproterenol. The intrinsic activities of compounds 10 and 12 were equal to that of (-)-isoproterenol. The intrinsic activities of compounds 11 and 13 were 1.3 and 1.2 times that of (-)-isoproterenol, respectively. Treatment of membrane preparations with bromoacetamido derivative 13 resulted in an irreversible loss of binding sites, and thus, 13 seems to be an alkylating affinity label for beta-adrenoceptors.

  DOI：

  10.1021/jm00392a006

文献信息

• BAKER, STEPHEN P.;PITHA, JOSEF
  作者：BAKER, STEPHEN P.、PITHA, JOSEF

  DOI：——

  日期：——
• MILECKI, JAN;BAKER, STEPHEN P.;STANDIFER, KELLY M.;ISHIZU, TAKASHI;CHIDA,+, J. MED. CHEM., 30,(1987) N 9, 1563-1566
  作者：MILECKI, JAN、BAKER, STEPHEN P.、STANDIFER, KELLY M.、ISHIZU, TAKASHI、CHIDA,+

  DOI：——

  日期：——
• US4894219A
  申请人：——

  公开号：US4894219A

  公开（公告）日：1990-01-16
• Carbostyril derivatives having potent .beta.-adrenergic agonist properties
  作者：Jan Milecki、Stephen P. Baker、Kelly M. Standifer、Takashi Ishizu、Yasuhiro Chida、John W. Kusiak、Josef Pitha

  DOI：10.1021/jm00392a006

  日期：1987.9

  Derivatives carrying a substituent in the para position of the phenyl group of 8-hydroxy-5-[2-[(1-phenyl-2-methylprop-2-yl)amino]-1-hydroxyethyl] carbostyril (10) were prepared and their effects on beta-adrenoceptors evaluated in vitro. Unsubstituted compound 10, iodo 11, amino 12, and bromoacetamido 13 derivatives (all racemic) bound to the receptor with 15-100-fold lower dissociation constants than that of (-)-isoproterenol. All the above compounds stimulated adenylate cyclase more potently than (-)-isoproterenol. The intrinsic activities of compounds 10 and 12 were equal to that of (-)-isoproterenol. The intrinsic activities of compounds 11 and 13 were 1.3 and 1.2 times that of (-)-isoproterenol, respectively. Treatment of membrane preparations with bromoacetamido derivative 13 resulted in an irreversible loss of binding sites, and thus, 13 seems to be an alkylating affinity label for beta-adrenoceptors.