4-propyl-2-(pyrrolidin-1-yl)-5H-pyrimido[4,5-b][1,4]benzothiazine | 1423655-64-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-propyl-2-(pyrrolidin-1-yl)-5H-pyrimido[4,5-b][1,4]benzothiazine
• 英文别名: 4-propyl-2-pyrrolidin-1-yl-5H-pyrimido[4,5-b][1,4]benzothiazine
• CAS: 1423655-64-4
• 化学式: C₁₇H₂₀N₄S
• 分子量: 312.439
• InChiKey: MDILITCSDMQJIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙硫氧嘧啶 在 水 、 溴 、 sodium amide 、 三乙胺 、 氯乙酸 、 三氯氧磷 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 反应 8.0h， 生成 4-propyl-2-(pyrrolidin-1-yl)-5H-pyrimido[4,5-b][1,4]benzothiazine
  参考文献：
  名称：

  Synthesis of new series of pyrimido[4,5-b][1,4] benzothiazines as 15-lipoxygenase inhibitors and study of their inhibitory mechanism

  摘要：

  A series of 2-substituted 4-n-propyl pyrimido[4,5-b][1,4]benzothiazines were synthesized, and evaluated as soybean 15-lipoxygenase (SLO) inhibitors. Among the synthesized compounds, 2-(4-methyl piperazinyl) analog showed the best SLO inhibition activity (IC50 = 8.9 +/- A 0.4 mu M). To rationalize the inhibitory potency variation of the compounds, computer-assisted modeling of the enzyme-inhibitor, radical scavenging evaluation, and inhibitory mechanism analyses were performed. The results showed that in 4-alkyl pyrimido[4,5-b]benzothiazines with same 2-substituent, radical scavenging potency plays a key role in lipoxygenase inhibition.

  DOI：

  10.1007/s00044-013-0506-7

文献信息

• Synthesis of new series of pyrimido[4,5-b][1,4] benzothiazines as 15-lipoxygenase inhibitors and study of their inhibitory mechanism
  作者：Mohsen Nikpour、Mina Mousavian、Mahdieh Davoodnejad、Maliheh Alimardani、Hamid Sadeghian

  DOI：10.1007/s00044-013-0506-7

  日期：2013.10

  A series of 2-substituted 4-n-propyl pyrimido[4,5-b][1,4]benzothiazines were synthesized, and evaluated as soybean 15-lipoxygenase (SLO) inhibitors. Among the synthesized compounds, 2-(4-methyl piperazinyl) analog showed the best SLO inhibition activity (IC50 = 8.9 +/- A 0.4 mu M). To rationalize the inhibitory potency variation of the compounds, computer-assisted modeling of the enzyme-inhibitor, radical scavenging evaluation, and inhibitory mechanism analyses were performed. The results showed that in 4-alkyl pyrimido[4,5-b]benzothiazines with same 2-substituent, radical scavenging potency plays a key role in lipoxygenase inhibition.