5,6-dihydro-8,9-dimethoxy-1-(4-methoxyphenyl)-pyrrolo[2,3-a]isoquinoline-2,3-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 5,6-dihydro-8,9-dimethoxy-1-(4-methoxyphenyl)-pyrrolo[2,3-a]isoquinoline-2,3-dione
• 英文别名: 8,9-dimethoxyl-1-(4-methoxyphenyl)-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-2,3-dione；KW-7；8,9-Dimethoxy-1-(4-methoxyphenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2,3-dione
• 化学式: C₂₁H₁₉NO₅
• 分子量: 365.386
• InChiKey: GGLCESZWPRZVIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-[2-(3,4-二甲氧基苯基)乙基]-4-甲氧基苯基乙酰胺 在 吡啶 、 三氯氧磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 5,6-dihydro-8,9-dimethoxy-1-(4-methoxyphenyl)-pyrrolo[2,3-a]isoquinoline-2,3-dione
  参考文献：
  名称：

  Antiplatelet activity of synthetic pyrrolo-benzylisoquinolines

  摘要：

  Pyrrolo-benzylisoquinolines were prepared as target compounds and their antiplatelet aggregation activity, adrenoreceptor affinity, and cytotoxicity were screened. Compounds 1d-9d showed specific antiplatelet aggregation activity induced by arachidonic acid and collagen. Among them, 8d and 9d exhibited better activity than the reference drug, aspirin and 9d also showed inhibition of platelet aggregation by all four inducers. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00003-9

文献信息

• Synthesis of Homoprotoberberines and 8-Oxoprotoberberines by Sequential Bicyclization of Phenylacetamides
  作者：Rafael Suau、Juan Manuel López-Romero、Antonio Ruiz、Rodrigo Rico

  DOI：10.1016/s0040-4020(99)01084-4

  日期：2000.2

  The reaction of phenylacetamides with oxalyl chloride/Lewis acid provides a convergent, high-yield entry to C-homoprotoberberine and 8-oxoprotoberberine alkaloids from available starting materials. This approach was used to synthesize 8-oxopseudopalmatine starting from N-[β-(3′,4′-dimethoxyphenyl)ethyl]-3,4-dimethoxyphenylacetamide. Some C-homoprotoberberines exhibit significant cytotoxicity against

  苯乙酰胺与草酰氯/路易斯酸的反应提供了从可用起始原料到C-高伯小ber碱和8-氧伯小o碱生物碱的收敛，高收率的入口。该方法用于从N- [β-（3'，4'-二甲氧基苯基）乙基] -3,4-二甲氧基苯基乙酰胺开始合成8-氧代伪巴马汀。一些C-同型小ber碱对人乳腺癌细胞显示出显着的细胞毒性。