4-Methyl-2-phenyl-6-propyl-5,6-dihydro-4H-[1,3]thiazin-4-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 4-Methyl-2-phenyl-6-propyl-5,6-dihydro-4H-[1,3]thiazin-4-ol
• 英文别名: 4-methyl-2-phenyl-6-propyl-5,6-dihydro-1,3-thiazin-4-ol
• 化学式: C₁₄H₁₉NOS
• 分子量: 249.377
• InChiKey: ZAUCPOFUMIAKHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-庚烯-2-酮 、 硫代苯甲酰胺 在 三氟化硼乙醚 作用下， 生成 4-Methyl-2-phenyl-6-propyl-5,6-dihydro-4H-[1,3]thiazin-4-ol 、 4-Methyl-2-phenyl-6-propyl-5,6-dihydro-4H-[1,3]thiazin-4-ol
  参考文献：
  名称：

  Synthesis of 1,3-thiazine derivatives and their evaluation as potential antimycobacterial agents

  摘要：

  A series of eight 5,6-dihydro-4H-1,3-thiazine derivatives was synthesized by the BF3.Et2O-catalyzed reaction of selected alpha,beta-unsaturated ketones with thiobenzamide at room temperature. The antimycobacterial activities of these compounds were determined against Mycobacterium tuberculosis H37Rv (ATCC 27294) using the Alamar blue susceptibility assay. Three compounds, 5-hydroxy-3-phenyl-4-aza-2-thiabicyclo[3.3.1]none-3-ene 3a, 4-hydroxy-4-methyl-6-pentyl-2-phenyl-5,6-dihydro-4H-1,3-thiazine 3b, and 4-ethyl-4hydroxy-2-phenyl-5,6-dihydro-4H-1,3-thiazine 3c exhibited inhibitory activities of 97, 77 and 76%, respectively, at a concentration of 6.25 mug/ml. The actual MIC99 for the most active of these compounds, 3a, was also determined to be >6.25 mug/ml. These results, and especially those for 3a, suggest that 1,3-thiazines are potential lead compounds in the search for new antitubercular agents. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0928-0987(02)00014-3