(3,4-diphenyl-pyrrol-1-yl)phenylmethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (3,4-diphenyl-pyrrol-1-yl)phenylmethanone
• 英文别名: (3,4-diphenyl-1H-pyrrol-1-yl)(phenyl)methanone；(3,4-Diphenylpyrrol-1-yl)-phenylmethanone
• 化学式: C₂₃H₁₇NO
• 分子量: 323.394
• InChiKey: NBSSFRUGVGWDIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,4-diphenyl-1H-pyrrole-2,5-dicarboxylic acid 在 正丁基锂 、 C.I.酸性橙108 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (3,4-diphenyl-pyrrol-1-yl)phenylmethanone
  参考文献：
  名称：

  Structure-activity relationships study of neolamellarin A and its analogues as hypoxia inducible factor-1 (HIF-1) inhibitors

  摘要：

  The novel marine pyrrole alkaloid neolamellarin A derived from sponge has been shown to inhibit hypoxia-induced HIF-1 activity. In this work, we designed and synthesized neolamellarin A and its series of derivatives by a convergent synthetic strategy. The HIF-1 inhibitory activity and cytotoxicity of these compounds were evaluated in Hela cells by dual-luciferase reporter gene assay and MIT assay, respectively. The results showed that neolamellarin A 1 (IC50 = 10.8 +/- 1.0 mu M) and derivative 2b (IC50 = 11.9 +/- 3.6 mu M) had the best HIF-1 inhibitory activity and low cytotoxicity. Our SAR research focused on the effects of key regions aliphatic carbon chain length, aromatic ring substituents and C-7 substituent on biological activity, providing a basis for the subsequent research on the development of novel pyrrole alkaloids as HIF-1 inhibitors and design of small molecule probes for target protein identification.

  DOI：

  10.1016/j.bmcl.2019.06.017

文献信息

• Copper-catalyzed synthesis of five-membered heterocycles via double C–N bond formation: an efficient synthesis of pyrroles, dihydropyrroles, and carbazoles
  作者：Ende Li、Xiaobing Xu、Hongfeng Li、Huimin Zhang、Xiaolei Xu、Xiyuan Yuan、Yanzhong Li

  DOI：10.1016/j.tet.2009.08.075

  日期：2009.10

  An efficient copper-catalyzed double C-N bond forming reaction using diiodides and nitrogen-centered nucleophiles including amides and carbamates is reported. The reactions proceed to afford di- or tri-substituted N-acylpyrroles, dihydropyrroles, and carbazoles in good to excellent yields when different such as 1,4-diiodo-1,3-butadienes, 1,4-dihalobut-1-enes, and 2,2'-diiodobiphenyls were employed, respectively. It is crucial to use CuI as the catalyst with the assistance of proper base and diamine ligand. (C) 2009 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Double <i>N</i>-Alkenylation of Amides:  An Efficient Synthesis of Di- or Trisubstituted <i>N</i>-Acylpyrroles
  作者：Xiyuan Yuan、Xiaobing Xu、Xiaobo Zhou、Jiwei Yuan、Lugen Mai、Yanzhong Li

  DOI：10.1021/jo062194s

  日期：2007.2.1

  An efficient copper-catalyzed double alkenylation of amides with (1Z,3Z)-1,4-diiodo-1,3-dienes is reported for the first time. The reactions proceed to afford di- or trisubstituted N-acylpyrroles in good to excellent yields using CuI as the catalyst, Cs2CO3 as the base, and rac-trans-N,N'-dimethylcyclohexane-1,2-diamine as the ligand.