methyl 1,2-dibromo-8-isopropoxy-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate | 850346-76-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 1,2-dibromo-8-isopropoxy-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• 英文别名: Methyl 1,2-dibromo-9-methoxy-8-propan-2-yloxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
• CAS: 850346-76-8
• 化学式: C₁₈H₁₉Br₂NO₄
• 分子量: 473.161
• InChiKey: RFSVPYKHCRIEAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1,2-dibromo-8-isopropoxy-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 在 四(三苯基膦)钯 、 三氯化铝 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.34h， 生成 8-Hydroxy-1,2-bis-(3-hydroxy-phenyl)-9-methoxy-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Study of Potent Cytotoxic Analogues of the Marine Alkaloid Lamellarin D

  摘要：

  The marine alkaloid, Lamellarin D (Lam-D), has shown potent cytotoxicity in numerous cancer cell lines and was recently identified as a potent topoisomerase I inhibitor. A library of open lactone analogues of Lam-D was prepared from a methyl 5,6-dihydropyrrolo[2,1-a] isoquinoline-3- carboxylate scaffold (1) by introducing various aryl groups through sequential and regioselective bromination, followed by Pd(0)-catalyzed Suzuki cross-coupling chemistry. The compounds were obtained in a 24-44% overall yield, and tested in a panel of three human tumor cell lines, MDA-MB-231 (breast), A-549 (lung), and HT-29 (colon), to evaluate their cytotoxic potential. From these data, the SAR study concluded that more than 75% of the open-chain Lam-D analogues tested showed cytotoxicity in a low micromolar GI(50) range.

  DOI：

  10.1021/jm0602458
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 在 bis-triphenylphosphine-palladium(II) chloride N-溴代丁二酰亚胺(NBS) 、 sodium methylate 、 sodium hydride 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 1,2-dibromo-8-isopropoxy-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
  参考文献：
  名称：

  5,6-Dihydropyrrolo[2,1-b]isoquinolines as scaffolds for synthesis of lamellarin analogues

  摘要：

  Efficient modular synthetic routes to open chain marine alkaloids such as lamellarins have been developed. 5,6-Dihydropyrrolo[2, 1-b]isoquinoline scaffolds were prepared, and protocols enabling regioselective bromination followed by Suzuki cross-coupling were established for the introduction of aryl groups onto the 2- and 3-positions. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.145