5,6-dihydro-8,9-dimethoxy-2-phenylpyrrolo[2,1-a]isoquinoline-1-carbonitrile | 1053176-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5,6-dihydro-8,9-dimethoxy-2-phenylpyrrolo[2,1-a]isoquinoline-1-carbonitrile
• 英文别名: 8,9-dimethoxy-2-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carbonitrile
• CAS: 1053176-30-9
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: JTBJWYNTBOPWHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-8,9-dimethoxy-2-phenylpyrrolo[2,1-a]isoquinoline-1-carbonitrile 、 氯化重氮苯 在 吡啶 作用下， 以70%的产率得到3-phenylazo-5,6-dihydro-8,9-dimethoxy-2-phenylpyrrolo[2,1-a]isoquinoline-1-carbonitrile
  参考文献：
  名称：

  Synthesis of annulated dihydroisoquinoline heterocycles via their nitrogen ylides

  摘要：

  3,4-Dihydro-6,7-dimethoxyisoquinoline-1-acetonitrile reacts with some alpha-bromoketones in dry benzene to give the Corresponding isoquinolinium salts, which undergo intramolecular cyclization to give pyrrolo[2,1-a]isoquinolines. Cross-coupling of the latter compounds with some aryldiazonium chlorides resulted in the formation of 3-arylhydrazonopyrrolo[2,1-a]isoquinolines, 3-arylazopyrrolo[2,1-a]isoquinolines and 3-aryl-1,2,3-triazolo[5,1-a]isoquinolines, respectively. The structures of the products were established on the basis of their elemental and spectral analyses as well as X-ray single crystal studies. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.043
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 sodium carbonate 、 sodium iodide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 丙酮 为溶剂， 反应 39.17h， 生成 5,6-dihydro-8,9-dimethoxy-2-phenylpyrrolo[2,1-a]isoquinoline-1-carbonitrile
  参考文献：
  名称：

  A single‐step synthesis of 5,6‐dihydropyrrolo[2,1‐a]isoquinolines and evaluation of their anti‐leukemic activity

  摘要：

  While a pharmaceutically intriguing scaffold, 5,6‐dihydropyrrolo[2,1‐a]isoquinoline (DHPIQ), has precedently been prepared from diverse tetrahydroisoquinolines (THIQs) using elaborate conditions, convenient metal‐free methods were discovered from condensation of cyanomethylene‐THIQ (1) and α‐halo‐ketones or aldehydes (1a) to afford 15 DHPIQs (2–16) in moderate yields by employing unique reactivities of the secondary amine and α‐carbon to the nitrile of 1. Preliminary biological studies with chronic myelogenous leukemia K562 and adriamycin‐resistant K562 (K562/ADM) cells exhibited some of the DHPIQs tested were active in the both cell lines. In particular, cyclohexyl‐fused DHPIQ (10) showed GI50 values of 9.79 and 13.60 μM in K562 and K562/ADM cells, respectively. Based on the flow cytometry analysis of 10, the anti‐cancer activity could be from apoptosis‐related mechanisms. Overall, this DHPIQ scaffold may be further optimized to discover clinically meaningful anti‐leukemic agents overcoming adriamycin resistance.

  DOI：

  10.1002/bkcs.12846