4,5-dibromo-N-(4-methoxybenzyl)-1H-pyrrole-2-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-dibromo-N-(4-methoxybenzyl)-1H-pyrrole-2-carboxamide
• 化学式: C₁₃H₁₂Br₂N₂O₂
• 分子量: 388.058
• InChiKey: JPKQAEPDQBZDMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.12
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,2,2-三氯-1-(4,5-二溴-1H-吡咯-2-基)-1-乙酮 、 4-甲氧基苄胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以35%的产率得到4,5-dibromo-N-(4-methoxybenzyl)-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Synthesis and anticancer activity of focused compound libraries from the natural product lead, oroidin

  摘要：

  Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl) allyl)-4,5-dibromo-1H-pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screening in a panel of twelve cancer cell lines revealed 1 to be poorly cytotoxic with the 50% growth inhibition concentration (GI(50)) of 42 mu M in MCF-7 (breast) cells and 24 mu M in A2780 (ovarian) cells and >50 mu M in all other cell lines tested. The development of eight focused libraries comprising thirty compounds total identified N-(biphenyl-4-ylmethyl)-1H-pyrrole-2-carboxamide (4l), N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (5a) and N-(biphenyl-4-ylmethyl)-4,5-dibromo-1H-pyrrole-2-carboxamide (5l) as potent inhibitors of cell growth in our panel of cell lines. Of these compounds GI(50) values of <5 mu M were observed with 4l against HT29 (colon) and SW480 (colon); 5a against HT29; and 5l against HT29, SW480, MCF-7, A431 (skin), Du145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas) cell lines. As a cancer class, colon cancer appears to be more sensitive to the oroidin series of compounds, with analogue 5l being the most active. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.021

文献信息

• Synthesis and anticancer activity of focused compound libraries from the natural product lead, oroidin
  作者：Lauren Dyson、Anthony D. Wright、Kelly A. Young、Jennette A. Sakoff、Adam McCluskey

  DOI：10.1016/j.bmc.2014.01.021

  日期：2014.3

  Oroidin (1), (E)-N-(3-(2-amino-1H-imidazol-4-yl) allyl)-4,5-dibromo-1H-pyrrole-2-carboxamide, is a pyrrole alkaloid isolated from the marine sponge Agelas oroides. Routine screening in a panel of twelve cancer cell lines revealed 1 to be poorly cytotoxic with the 50% growth inhibition concentration (GI(50)) of 42 mu M in MCF-7 (breast) cells and 24 mu M in A2780 (ovarian) cells and >50 mu M in all other cell lines tested. The development of eight focused libraries comprising thirty compounds total identified N-(biphenyl-4-ylmethyl)-1H-pyrrole-2-carboxamide (4l), N-benzyl-4,5-dibromo-1H-pyrrole-2-carboxamide (5a) and N-(biphenyl-4-ylmethyl)-4,5-dibromo-1H-pyrrole-2-carboxamide (5l) as potent inhibitors of cell growth in our panel of cell lines. Of these compounds GI(50) values of <5 mu M were observed with 4l against HT29 (colon) and SW480 (colon); 5a against HT29; and 5l against HT29, SW480, MCF-7, A431 (skin), Du145 (prostate), BE2-C (neuroblastoma) and MIA (pancreas) cell lines. As a cancer class, colon cancer appears to be more sensitive to the oroidin series of compounds, with analogue 5l being the most active. (C) 2014 Elsevier Ltd. All rights reserved.