2-(3-hydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one | 1415662-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3-hydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one
• 英文别名: 2-(3-Hydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one
• CAS: 1415662-34-8
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: TUITUIWAVUZKLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氰乙酰肼 、 3-羟基苯乙酮 以 溶剂黄146 为溶剂， 反应 4.0h， 以70%的产率得到2-(3-hydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one
  参考文献：
  名称：

  Synthesis, characterization, biological evaluation and in silico screening of oxadiazinanones

  摘要：

  A series of novel oxadiazinan-5-one namely 2-methyl-2-phenyl-1,3,4-oxadiazinan-5-one (6), 2-(3-hydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one (7), 2-(4-hydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one (8), 2-(2,4-dihydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one (9) and 2-(2,5-dihydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one (10) have been synthesized by the reaction of acetophenone and its derivatives with cyanoacetic acid hydrazide. The structural assignments of the products were done on the basis of IR, H-1 NMR, C-13 NMR, MS, and analytical data. The in vitro antioxidant and antimicrobial activity of all the synthesized compounds (6-10) was tested by the DPPH and disk diffusion method, respectively. The synthesized compounds were screened against Gram-positive and Gram-negative bacterial and fungal strains. Compound (7) showed the highest inhibition comparable with the standard antibiotic drugs Ciprofloxacin and Amphotericin B. The antibacterial activity of the synthesized compounds was further investigated with the help of in silico docking study using Discovery studio 3.1, Molego Virtual Docker and LigandScout to predict the active sites.

  DOI：

  10.1007/s00044-012-0313-6

文献信息

• Synthesis, characterization, biological evaluation and in silico screening of oxadiazinanones
  作者：Mehtab Parveen、Akhtar Ali、Mahboob Alam、Asad U. Khan、Anis Ahmad

  DOI：10.1007/s00044-012-0313-6

  日期：2013.7

  A series of novel oxadiazinan-5-one namely 2-methyl-2-phenyl-1,3,4-oxadiazinan-5-one (6), 2-(3-hydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one (7), 2-(4-hydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one (8), 2-(2,4-dihydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one (9) and 2-(2,5-dihydroxyphenyl)-2-methyl-1,3,4-oxadiazinan-5-one (10) have been synthesized by the reaction of acetophenone and its derivatives with cyanoacetic acid hydrazide. The structural assignments of the products were done on the basis of IR, H-1 NMR, C-13 NMR, MS, and analytical data. The in vitro antioxidant and antimicrobial activity of all the synthesized compounds (6-10) was tested by the DPPH and disk diffusion method, respectively. The synthesized compounds were screened against Gram-positive and Gram-negative bacterial and fungal strains. Compound (7) showed the highest inhibition comparable with the standard antibiotic drugs Ciprofloxacin and Amphotericin B. The antibacterial activity of the synthesized compounds was further investigated with the help of in silico docking study using Discovery studio 3.1, Molego Virtual Docker and LigandScout to predict the active sites.