N-phenethyl-1H-pyrrole-2-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-phenethyl-1H-pyrrole-2-carboxamide
• 英文别名: N-2-phenylethyl-1H-pyrrole-2-carboxamide；N-(2-phenylethyl)-1H-pyrrole-2-carboxamide
• 化学式: C₁₃H₁₄N₂O
• mdl: MFCD17710466
• 分子量: 214.267
• InChiKey: JSHPCVXIXZUURL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 、 2-苯乙胺 在 三乙胺 作用下， 以87%的产率得到N-phenethyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  New Pyrrole Inhibitors of Monoamine Oxidase:  Synthesis, Biological Evaluation, and Structural Determinants of MAO-A and MAO-B Selectivity

  摘要：

  A series of new pyrrole derivatives have been synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. N-Methyl,N-(benzyl),N-(pyrrol-2-ylmethyl)amine (7) and N-(2-benzyl),N-(1-methylpyrrol-2-ylmethyl)amine (18) were the most selective MAO-B (7, SI = 0.0057) and MAO-A (18, SI = 12500) inhibitors, respectively. Docking and molecular dynamics simulations gave structural insights into the MAO-A and MAO-B selectivity. Compound 18 forms an H-bond with Gln215 through its protonated amino group into the MAO-A binding site. This H-bond is absent in the 7/MAO-A complex. In contrast, compound 7 places its phenyl ring into an aromatic cage of the MAO-B binding pocket, where it forms charge-transfer interactions. The slightly different binding pose of 18 into the MAO-B active site seems to be forced by a bulkier Tyr residue, which replaces a smaller Ile residue present in MAO-A.

  DOI：

  10.1021/jm060882y

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.
• N-Benzyl, N-phenethyl and N-benzyloxybenzamide derivatives inhibit amyloid-beta (Aβ42) aggregation and mitigate Aβ42-induced neurotoxicity
  作者：Yusheng Zhao、Arash Shakeri、Ahmed A. Hefny、Praveen P. N. Rao

  DOI：10.1007/s00044-024-03256-6

  日期：2024.7