4,6-dimethoxy-2,2-bis((4-methylpiperazin-1-yl)methyl)benzofuran-3(2H)-one | 1233972-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4,6-dimethoxy-2,2-bis((4-methylpiperazin-1-yl)methyl)benzofuran-3(2H)-one
• 英文别名: 4,6-Dimethoxy-2,2-bis[(4-methylpiperazin-1-yl)methyl]-1-benzofuran-3-one
• CAS: 1233972-68-3
• 化学式: C₂₂H₃₄N₄O₄
• 分子量: 418.536
• InChiKey: LKYMYHKPURVJNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-甲基哌嗪 、 聚合甲醛 、 4,6-二甲氧基-1-苯并呋喃-3(2H)-酮 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 以55%的产率得到4,6-dimethoxy-2,2-bis((4-methylpiperazin-1-yl)methyl)benzofuran-3(2H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents

  摘要：

  This is the first report on aurones as a new class of drugs with anti-inflammatory and antimicrobial agents. A series of 2,2-bisaminomethylated aurone analogues (4a-j) were synthesized by Mannich reaction from 1,3,5-trimethoxybenzene in three steps. The structures of the newly synthesized compounds were confirmed by IR, H-1 NMR and mass spectral analysis. All the synthesized compounds were screened against the pro-inflammatory cytokines (TNF-alpha, IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 4a, 4b, 4c, 4d, and 4e showed promising results against IL-6 at 10 mu M concentration (74-100%). Compounds 4a, 4b and 4c were found to be active against TNF-alpha (76-100%) at 10 mu M. Interestingly, all compounds have shown good antimicrobial activity. Compounds 4d, 4e and 4f showed excellent antimicrobial activity as compared with standard drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.045

文献信息

• Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents
  作者：Babasaheb P. Bandgar、Sachin A. Patil、Balaji L. Korbad、Satish C. Biradar、Shivraj N. Nile、Chandrahasya N. Khobragade

  DOI：10.1016/j.ejmech.2010.03.045

  日期：2010.7

  This is the first report on aurones as a new class of drugs with anti-inflammatory and antimicrobial agents. A series of 2,2-bisaminomethylated aurone analogues (4a-j) were synthesized by Mannich reaction from 1,3,5-trimethoxybenzene in three steps. The structures of the newly synthesized compounds were confirmed by IR, H-1 NMR and mass spectral analysis. All the synthesized compounds were screened against the pro-inflammatory cytokines (TNF-alpha, IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 4a, 4b, 4c, 4d, and 4e showed promising results against IL-6 at 10 mu M concentration (74-100%). Compounds 4a, 4b and 4c were found to be active against TNF-alpha (76-100%) at 10 mu M. Interestingly, all compounds have shown good antimicrobial activity. Compounds 4d, 4e and 4f showed excellent antimicrobial activity as compared with standard drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.