(3,4-bis(4-methoxyphenyl)-1H-pyrrol-1-yl)(phenyl)methanone | 65112-26-7

• 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-bis(4-methoxyphenyl)-1H-pyrrol-1-yl)(phenyl)methanone
• 英文别名: 1-Benzoyl-3,4-bis(4'-methoxyphenyl)pyrrol；1-benzoyl-3,4-bis-(4-methoxy-phenyl)-pyrrole；[3,4-Bis(4-methoxyphenyl)pyrrol-1-yl]-phenylmethanone
• CAS: 65112-26-7
• 化学式: C₂₅H₂₁NO₃
• 分子量: 383.447
• InChiKey: JTGVKLZBAAYSSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,4-bis(4-methoxyphenyl)-1H-pyrrol-1-yl)(phenyl)methanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以69%的产率得到(3,4-bis(4-hydroxyphenyl)-1H-pyrrol-1-yl)(phenyl)methanone
  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
• 作为产物：
  描述：

  苯甲酸 在 正丁基锂 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (3,4-bis(4-methoxyphenyl)-1H-pyrrol-1-yl)(phenyl)methanone
  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