5-bromo-2-(5-(2-bromoacetyl)-2-propoxyphenyl)-6-isopropylpyrimidin-4(3H)-one | 1229017-68-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-bromo-2-(5-(2-bromoacetyl)-2-propoxyphenyl)-6-isopropylpyrimidin-4(3H)-one
• 英文别名: 5-bromo-6-isopropyl-2-(5-(2-bromoacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one；5-Bromo-6-isopropyl-2-(5-(2-bromoacetyl)-2-n-propoxyphenyl)pyrimid-4(3H)-one；5-bromo-2-[5-(2-bromoacetyl)-2-propoxyphenyl]-4-propan-2-yl-1H-pyrimidin-6-one
• CAS: 1229017-68-8
• 化学式: C₁₈H₂₀Br₂N₂O₃
• 分子量: 472.176
• InChiKey: DCAVAHWRVMSRSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(5-(2-bromoacetyl)-2-propoxyphenyl)-6-isopropylpyrimidin-4(3H)-one 、 N-甲基哌嗪 生成 5-bromo-6-isopropyl-2-(5-(2-(4-methylpiperazin-1-yl)acetyl)-2-propoxyphenyl)pyrimidin-4(3H)-one
  参考文献：
  名称：

  Phenylpyrimidone compounds, the pharmaceutical compositions, preparation methods and uses thereof

  摘要：

  本发明涉及一类苯基嘧啶酮化合物、制药组合物、制备方法及其用途。更具体地说，本发明涉及以下式I的一类苯基嘧啶酮化合物、其药学上可接受的盐或溶剂和药物组合物以及化合物的制备方法。本发明的式I化合物能够有效地抑制V型磷酸二酯酶（PDE5），因此可以用于治疗各种血管障碍，例如男性勃起功能障碍、肺动脉高压等。

  公开号：

  US08871777B2
• 作为产物：
  描述：

  5-bromo-2-(5-bromo-2-propoxyphenyl)-6-isopropylpyrimidin-4(3H)-one 在 溴 、 palladium diacetate 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 5-bromo-2-(5-(2-bromoacetyl)-2-propoxyphenyl)-6-isopropylpyrimidin-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

• Phenylpyrimidone Compounds, the Pharmaceutical Compositions, Preparation Methods and Uses Thereof
  申请人：Liu Zheng

  公开号：US20110301109A1

  公开（公告）日：2011-12-08

  The present invention relates to a class of phenylpyrimidone compounds, the pharmaceutical composition, the preparation method and the use thereof. More specifically, the present invention relates to a type of phenylpyrimidone compounds of the following formula I, the pharmaceutically acceptable salts or solvates thereof and to the pharmaceutical composition as well as the preparation method of the compounds. The compounds of formula I according to the present invention can effectively inhibit type V phosphodiesterase (PDE5), and thus can be used for the treatment of various vascular disorders, such as male erectile dysfunction, pulmonary hypertension and the like.

  本发明涉及一类苯基嘧啶酮化合物、制药组合物、其制备方法和用途。更具体地说，本发明涉及以下式I的一类苯基嘧啶酮化合物、其制药学上可接受的盐或溶剂以及化合物的制药组合物和制备方法。根据本发明的式I化合物可以有效抑制第V型磷酸二酯酶（PDE5），因此可以用于治疗各种血管障碍，例如男性勃起功能障碍、肺动脉高压等。
• Phenylpyrimidone compounds, the pharmaceutical compositions, preparation methods and uses thereof
  申请人：Liu Zheng

  公开号：US08871777B2

  公开（公告）日：2014-10-28

  The present invention relates to a class of phenylpyrimidone compounds, the pharmaceutical composition, the preparation method and the use thereof. More specifically, the present invention relates to a type of phenylpyrimidone compounds of the following formula I, the pharmaceutically acceptable salts or solvates thereof and to the pharmaceutical composition as well as the preparation method of the compounds. The compounds of formula I according to the present invention can effectively inhibit type V phosphodiesterase (PDE5), and thus can be used for the treatment of various vascular disorders, such as male erectile dysfunction, pulmonary hypertension and the like.

  本发明涉及一类苯基嘧啶酮化合物、制药组合物、制备方法及其用途。更具体地说，本发明涉及以下式I的一类苯基嘧啶酮化合物、其药学上可接受的盐或溶剂和药物组合物以及化合物的制备方法。本发明的式I化合物能够有效地抑制V型磷酸二酯酶（PDE5），因此可以用于治疗各种血管障碍，例如男性勃起功能障碍、肺动脉高压等。
• 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
• 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.