2-propoxy-5-(4-methylpiperazin-1-yl)sulphonylbenzonitrile | 1229019-31-1

• 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: 2-propoxy-5-(4-methylpiperazin-1-yl)sulphonylbenzonitrile
• 英文别名: 2-n-Propoxy-5-(4-methylpiperazin-1-yl)sulfonylbenzonitrile；5-[(4-Methyl-1-piperazinyl)sulfonyl]-2-propoxybenzonitrile；5-(4-methylpiperazin-1-yl)sulfonyl-2-propoxybenzonitrile
• CAS: 1229019-31-1
• 化学式: C₁₅H₂₁N₃O₃S
• 分子量: 323.416
• InChiKey: NORBQZOQWCGRSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-propoxy-5-(4-methylpiperazin-1-yl)sulphonylbenzonitrile 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 6-ethyl-2-[2-propoxy-5-(4-methyl-1-piperazinylsulfonyl)-phenyl]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Utilization of Halogen Bond in Lead Optimization: A Case Study of Rational Design of Potent Phosphodiesterase Type 5 (PDE5) Inhibitors

  摘要：

  For proof-of-concept of halogen bonding in drug design, a series of halogenated compounds were designed based on a lead structure as new inhibitors of phosphodiesterase type S. Bioassay results revealed a good correlation between the measured bioactivity and the calculated halogen bond energy. Our X-ray crystal structures verified the existence of the predicted halogen bonds, demonstrating that the halogen bond is an applicable tool in drug design and should be routinely considered in lead optimization.

  DOI：

  10.1021/jm200644r
• 作为产物：
  描述：

  2-丙氧基苯甲腈 在 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 2-propoxy-5-(4-methylpiperazin-1-yl)sulphonylbenzonitrile
  参考文献：
  名称：

  PHENYL PYRIMIDONE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, PREPARATION METHODS AND USES THEREOF

  摘要：

  公开号：

  EP2383262B1

文献信息

• PHENYL PYRIMIDONE COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, PREPARATION METHODS AND USES THEREOF
  申请人：Topharman Shanghai Co., Ltd.

  公开号：EP2383262B1

  公开（公告）日：2016-07-06
• US8871777B2
  申请人：——

  公开号：US8871777B2

  公开（公告）日：2014-10-28
• Utilization of Halogen Bond in Lead Optimization: A Case Study of Rational Design of Potent Phosphodiesterase Type 5 (PDE5) Inhibitors
  作者：Zhijian Xu、Zheng Liu、Tong Chen、TianTian Chen、Zhen Wang、Guanghui Tian、Jing Shi、Xuelan Wang、Yunxiang Lu、Xiuhua Yan、Guan Wang、Hualiang Jiang、Kaixian Chen、Shudong Wang、Yechun Xu、Jingshan Shen、Weiliang Zhu

  DOI：10.1021/jm200644r

  日期：2011.8.11

  For proof-of-concept of halogen bonding in drug design, a series of halogenated compounds were designed based on a lead structure as new inhibitors of phosphodiesterase type S. Bioassay results revealed a good correlation between the measured bioactivity and the calculated halogen bond energy. Our X-ray crystal structures verified the existence of the predicted halogen bonds, demonstrating that the halogen bond is an applicable tool in drug design and should be routinely considered in lead optimization.