5-溴-6-乙基嘧啶2,4-二胺 | 861103-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-溴-6-乙基嘧啶2,4-二胺
• 英文名称: 5-bromo-6-ethylpyrimidine 2,4-diamine
• 英文别名: 5-Bromo-6-ethyl-2,4-pyrimidinediamine；5-bromo-6-ethylpyrimidine-2,4-diamine
• CAS: 861103-60-8
• 化学式: C₆H₉BrN₄
• 分子量: 217.068
• InChiKey: LDBFUJOVNWPXMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-溴-6-乙基嘧啶2,4-二胺 、 4-(3-methoxypropyl)-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-benzo[b][1,4]oxazin-3(4H)-one 在 四(三苯基膦)钯 potassium phosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以22%的产率得到6-(2,4-diamino-6-ethylpyrimidin-5-yl)-4-(3-methoxypropyl)-2-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one
  参考文献：
  名称：

  Rational design of 6-(2,4-diaminopyrimidinyl)-1,4-benzoxazin-3-ones as small molecule renin inhibitors

  摘要：

  We report the design and synthesis of a series of 6-(2,4-diaminopyrimidinyl)-1,4-benzoxazin-3-ones as orally bioavailable small molecule inhibitors of renin. Compounds with a 2-methyl-2-aryl substitution pattern exhibit potent renin inhibition and good permeability, solubility, and metabolic stability. Oral bioavailability was found to be dependent on metabolic clearance and cellular permeability, and was optimized through modulation of the sidechain that binds in the S3(sp) subsite.

  DOI：

  10.1016/j.bmc.2007.05.069
• 作为产物：
  描述：

  2,4-二氨基-6-乙基嘧啶 在 溴 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以31%的产率得到5-溴-6-乙基嘧啶2,4-二胺
  参考文献：
  名称：

  Diaminopyrimidine derivatives as growth hormone secrectgogue receptor (GHS-R) antagonists

  摘要：

  本发明涉及式(I)的化合物，或其治疗上适用的盐或前药，所述化合物的制备，含有所述化合物的组合物以及在预防或治疗由胃泌素受体调节的疾病中使用所述化合物，包括普拉德-威利综合征、进食障碍、体重增加、饮食和锻炼后体重减轻维持、肥胖，以及与肥胖相关的疾病，如非胰岛素依赖型糖尿病。

  公开号：

  US20050171131A1

文献信息

• SUBSTITUTED BENZOXAZINONES
  申请人：Holsworth Daniel

  公开号：US20090215763A1

  公开（公告）日：2009-08-27

  The present invention provides substituted oxazinone compounds, such as substituted benzoxazinones, which exhibit potent renin inhibition activities.

  本发明提供了取代的噁唑酮化合物，例如取代的苯并噁唑酮，表现出强大的肾素抑制活性。
• SUBSTITUTED (S)-BENZOXAZINONES
  申请人：Holsworth Daniel

  公开号：US20090311318A1

  公开（公告）日：2009-12-17

  The present invention provides enantiomerically pure substituted (S)-benzoxazinone compounds and an extended release formulation of the compounds. The compounds exhibit potent renin inhibition activities and improved bioavailability.

  本发明提供了对映纯的取代(S)-苯并噁嗪酮化合物及这些化合物的缓释制剂。这些化合物表现出强效的肾素抑制活性和改善的生物利用度。
• Discovery of 6-ethyl-2,4-diaminopyrimidine-based small molecule renin inhibitors
  作者：Daniel D. Holsworth、Mehran Jalaie、Thomas Belliotti、Cuiman Cai、Wendy Collard、Suzie Ferreira、Noel A. Powell、Michael Stier、Erli Zhang、Pat McConnell、Igor Mochalkin、Michael J. Ryan、John Bryant、Tingsheng Li、Aparna Kasani、Rajendra Subedi、Samarendra N. Maiti、Jeremy J. Edmunds

  DOI：10.1016/j.bmcl.2007.04.052

  日期：2007.7

  Novel 2,4-diaminopyrimidine-based small molecule renin inhibitors are disclosed. Through high throughput screening, parallel synthesis, X-ray crystallography, and structure based drug design, we have developed the first non-chiral, non-peptidic, small molecular template to possess moderate potency against renin. The designed compounds consist of a novel 6-ethyl-5(1,2,3,4-tetrahydroquinolin-7-yl)pyrimidine-2,4-diamine ring system that exhibit moderate potency (IC50: 91-650 nM) against renin while remaining 'Rule-of-five' compliant. (c) 2007 Elsevier Ltd. All rights reserved.
• [EN] SUBSTITUTED BENZOXAZINONES<br/>[FR] BENZOXAZINONES SUBSTITUÉES
  申请人：P & H THERAPEUTICS INC

  公开号：WO2009108722A2

  公开（公告）日：2009-09-03

  The present invention provides substituted oxazinone compounds, such as substituted benzoxazinones, which exhibit potent renin inhibition activities.
• Rational design of 6-(2,4-diaminopyrimidinyl)-1,4-benzoxazin-3-ones as small molecule renin inhibitors
  作者：Noel A. Powell、Fred L. Ciske、Cuiman Cai、Daniel D. Holsworth、Ken Mennen、Chad A. Van Huis、Mehran Jalaie、Jacqueline Day、Michelle Mastronardi、Pat McConnell、Igor Mochalkin、Erli Zhang、Michael J. Ryan、John Bryant、Wendy Collard、Suzie Ferreira、Chungang Gu、Roxane Collins、Jeremy J. Edmunds

  DOI：10.1016/j.bmc.2007.05.069

  日期：2007.9

  We report the design and synthesis of a series of 6-(2,4-diaminopyrimidinyl)-1,4-benzoxazin-3-ones as orally bioavailable small molecule inhibitors of renin. Compounds with a 2-methyl-2-aryl substitution pattern exhibit potent renin inhibition and good permeability, solubility, and metabolic stability. Oral bioavailability was found to be dependent on metabolic clearance and cellular permeability, and was optimized through modulation of the sidechain that binds in the S3(sp) subsite.