1-[(2-bromophenyl)methyl]-3,4-dihydro-6-methoxy-1H-isoquinoline-2-carboxaldehyde | 1418222-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-[(2-bromophenyl)methyl]-3,4-dihydro-6-methoxy-1H-isoquinoline-2-carboxaldehyde
• CAS: 1418222-46-4
• 化学式: C₁₈H₁₈BrNO₂
• 分子量: 360.25
• InChiKey: CZVJFGQIFUIGQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-[(2-bromophenyl)methyl]-3,4-dihydro-6-methoxy-1H-isoquinoline-2-carboxaldehyde 在 硼烷四氢呋喃络合物 、 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 18.0h， 生成 dl-2-Methoxy-aporphin
  参考文献：
  名称：

  Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells

  摘要：

  Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a, 7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine-and benzylisoquinoline-type alkaloids. In addition, 3-30 mu M nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 mu M N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 mu M nuciferine inhibited the expression of TRP-2 mRNA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.038
• 作为产物：
  描述：

  2-(2-bromophenyl)-N-[2-(4-methoxyphenyl)ethyl]acetamide 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 1-[(2-bromophenyl)methyl]-3,4-dihydro-6-methoxy-1H-isoquinoline-2-carboxaldehyde
  参考文献：
  名称：

  Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells

  摘要：

  Methanolic extracts from the flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) were found to show inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extracts, a new alkaloid, N-methylasimilobine N-oxide, was isolated together with eleven benzylisoquinoline alkaloids. The absolute stereostructure of the new alkaloid was determined from chemical and physicochemical evidence. Among the constituents isolated, nuciferine, N-methylasimilobine, (-)-lirinidine, and 2-hydroxy-1-methoxy-6a, 7-dehydroaporphine showed potent inhibition of melanogenesis. Comparison of the inhibitory activities of synthetic related alkaloids facilitated characterization of the structure-activity relationships of aporphine-and benzylisoquinoline-type alkaloids. In addition, 3-30 mu M nuciferine and N-methylasimilobine inhibited the expression of tyrosinase mRNA, 3-30 mu M N-methylasimilobine inhibited the expression of TRP-1 mRNA, and 10-30 mu M nuciferine inhibited the expression of TRP-2 mRNA. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.038