2-Acetyl-3-hydroxybenzonitrile | 1356999-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetyl-3-hydroxybenzonitrile
• 英文别名: 2-acetyl-3-hydroxybenzonitrile
• CAS: 1356999-30-8
• 化学式: C₉H₇NO₂
• 分子量: 161.16
• InChiKey: WUWPAHCCHPSEQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,5-三甲氧基苯甲醛 、 2-Acetyl-3-hydroxybenzonitrile 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2′,4′,5′-trimethoxyflavonol derivatives as anti-inflammatory and antimicrobial agents

  摘要：

  A series of novel 3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (flavonol) derivatives (2a-u) of biological interest have been prepared via CLAISEN-SCHMIDT condensation followed by ALGAR-FLYNN-OYAMADA reaction and to search for the potent nonsteroidal anti-inflammatory agents from this novel series. All the synthesized compounds have been screened for their in vitro proinflammatory cytokines tumor necrosis factor (TNF-alpha) and interleukin-6 (IL-6) inhibitory activity along with antimicrobial activity. As many as three compounds viz. 2h, 2l, and 2q from this novel series were found to be potent TNF-alpha and IL-6 inhibitor (up to 72-81 % TNF-alpha and 86-92 % IL-6 inhibitory activity) but at 10 mu M concentration as compared with the standard dexamethasone (71 % TNF-alpha and 84 % IL-6 inhibitory activities at 1 mu M concentration). While the compounds 2d, 2m, 2n, and 2s were found to be potent antimicrobial agent showing even 2-2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL.

  DOI：

  10.1007/s00044-013-0651-z

文献信息

• Synthesis and biological evaluation of novel 2′,4′,5′-trimethoxyflavonol derivatives as anti-inflammatory and antimicrobial agents
  作者：Girish D. Hatnapure、Ashish P. Keche、Atish H. Rodge、Rajesh H. Tale、Satish S. Birajdar、Mahendra J. Pawar、Vandana M. Kamble

  DOI：10.1007/s00044-013-0651-z

  日期：2014.1

  A series of novel 3-hydroxy-2-(2,4,5-trimethoxyphenyl)-4H-chromen-4-one (flavonol) derivatives (2a-u) of biological interest have been prepared via CLAISEN-SCHMIDT condensation followed by ALGAR-FLYNN-OYAMADA reaction and to search for the potent nonsteroidal anti-inflammatory agents from this novel series. All the synthesized compounds have been screened for their in vitro proinflammatory cytokines tumor necrosis factor (TNF-alpha) and interleukin-6 (IL-6) inhibitory activity along with antimicrobial activity. As many as three compounds viz. 2h, 2l, and 2q from this novel series were found to be potent TNF-alpha and IL-6 inhibitor (up to 72-81 % TNF-alpha and 86-92 % IL-6 inhibitory activity) but at 10 mu M concentration as compared with the standard dexamethasone (71 % TNF-alpha and 84 % IL-6 inhibitory activities at 1 mu M concentration). While the compounds 2d, 2m, 2n, and 2s were found to be potent antimicrobial agent showing even 2-2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 mu g/mL.