5-bromo-2-(5-((4-methylpiperazin-1-yl)sulfonyl)-2-propoxyphenyl)-6-propylpyrimidin-4(3H)-one | 1449772-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-2-(5-((4-methylpiperazin-1-yl)sulfonyl)-2-propoxyphenyl)-6-propylpyrimidin-4(3H)-one
• 英文别名: 5-bromo-2-[5-(4-methylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-4-propyl-1H-pyrimidin-6-one
• CAS: 1449772-44-4
• 化学式: C₂₁H₂₉BrN₄O₄S
• 分子量: 513.456
• InChiKey: HUXIRPTUIBCBEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(5-((4-methylpiperazin-1-yl)sulfonyl)-2-propoxyphenyl)-6-propylpyrimidin-4(3H)-one 在 吡啶 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以82%的产率得到5-bromo-2-(5-((4-methylpiperazin-1-yl)sulfonyl)-2-propoxyphenyl)-6-propylpyrimidin-4(3H)-one
  参考文献：
  名称：

  Exploration of the 5-bromopyrimidin-4(3H)-ones as potent inhibitors of PDE5

  摘要：

  The substituents both at the 6-position of the 5-bromopyrimidinone ring and at the 5'-position of the phenyl ring of 5-bromopyrimidin-4(3H)-ones were explored. 5-Bromo-6-isopropyl-2-(2-propoxyphenyl)pyrimidin-4(3H)-one was identified as a new scaffold for potent PDE5 inhibitors. The crystal structures of PDE5/2e and PDE5/10a complexes provided a structural basis for the inhibition of 5-bromopyrimidinones to PDE5. In addition, it was also found that there is a great tolerance for the substitution at the 5'-position of the phenyl ring of 5-bormopyrimidinones and the resulted compound 13a has the highest inhibition activity to PDE5 (IC50, 1.7 nM). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.062

文献信息

• Exploration of the 5-bromopyrimidin-4(3H)-ones as potent inhibitors of PDE5
  作者：Xudong Gong、Guan Wang、Jing Ren、Zheng Liu、Zhen Wang、Tiantian Chen、Xiaojun Yang、Xiangrui Jiang、Jingshan Shen、Hualiang Jiang、Haji Akber Aisa、Yechun Xu、Jianfeng Li

  DOI：10.1016/j.bmcl.2013.06.062

  日期：2013.9

  The substituents both at the 6-position of the 5-bromopyrimidinone ring and at the 5'-position of the phenyl ring of 5-bromopyrimidin-4(3H)-ones were explored. 5-Bromo-6-isopropyl-2-(2-propoxyphenyl)pyrimidin-4(3H)-one was identified as a new scaffold for potent PDE5 inhibitors. The crystal structures of PDE5/2e and PDE5/10a complexes provided a structural basis for the inhibition of 5-bromopyrimidinones to PDE5. In addition, it was also found that there is a great tolerance for the substitution at the 5'-position of the phenyl ring of 5-bormopyrimidinones and the resulted compound 13a has the highest inhibition activity to PDE5 (IC50, 1.7 nM). (C) 2013 Elsevier Ltd. All rights reserved.