2-amino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine | 403792-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-amino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine
• 英文别名: 4-(1-Ethyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-amine；4-(3-ethyl-2-methylimidazol-4-yl)pyrimidin-2-amine
• CAS: 403792-92-7
• 化学式: C₁₀H₁₃N₅
• 分子量: 203.247
• InChiKey: SBIUSNLOEPXBRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine 、 N-甲基-4-溴苯甲酰胺 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-(4-(1-ethyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-ylamino)-N-methylbenzamide
  参考文献：
  名称：

  Imidazole pyrimidine amides as potent, orally bioavailable cyclin-dependent kinase inhibitors

  摘要：

  The development of a novel series of imidazole pyrimidine amides as cyclin-dependent kinase (CDK) inhibitors is described. The series was found to have much improved CDK2 inhibition and potent in vitro anti-proliferative effects against cancer cell lines. Control of overall lipophilicity was important to achieve good in vitro potency along with acceptable physiochemical properties and margins against inhibition of both CYP isoforms and the hERG potassium ion channel. A compound with an attractive overall balance of properties was pro. led in vivo and possessed suitable physiochemical and pharmacokinetic profiles for oral dosing. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.075
• 作为产物：
  描述：

  5-(3-dimethylaminoprop-2-en-1-oyl)-1-ethyl-2-methylimidazole 、 碳酸胍 以 正丁醇 为溶剂， 生成 2-amino-4-(1-ethyl-2-methylimidazol-5-yl)pyrimidine
  参考文献：
  名称：

  Imidazole pyrimidine amides as potent, orally bioavailable cyclin-dependent kinase inhibitors

  摘要：

  The development of a novel series of imidazole pyrimidine amides as cyclin-dependent kinase (CDK) inhibitors is described. The series was found to have much improved CDK2 inhibition and potent in vitro anti-proliferative effects against cancer cell lines. Control of overall lipophilicity was important to achieve good in vitro potency along with acceptable physiochemical properties and margins against inhibition of both CYP isoforms and the hERG potassium ion channel. A compound with an attractive overall balance of properties was pro. led in vivo and possessed suitable physiochemical and pharmacokinetic profiles for oral dosing. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.075

文献信息

• Imidazoles: SAR and development of a potent class of cyclin-dependent kinase inhibitors
  作者：Malcolm Anderson、David M. Andrews、Andy J. Barker、Claire A. Brassington、Jason Breed、Kate F. Byth、Janet D. Culshaw、M. Raymond V. Finlay、Eric Fisher、Helen H.J. McMiken、Clive P. Green、Dave W. Heaton、Ian A. Nash、Nicholas J. Newcombe、Sandra E. Oakes、Richard A. Pauptit、Andrew Roberts、Judith J. Stanway、Andrew P. Thomas、Julie A. Tucker、Mike Walker、Hazel M. Weir

  DOI：10.1016/j.bmcl.2008.09.024

  日期：2008.10

  An imidazole series of cyclin-dependent kinase (CDK) inhibitors has been developed. Protein inhibitor structure determination has provided an understanding of the emerging structure activity trends for the imidazole series. The introduction of a methyl sulfone at the aniline terminus led to a more orally bioavailable CDK inhibitor that was progressed into clinical development.
• IMIDAZOLO-5-YL-2-ANILINO-PYRIMIDINES AS AGENTS FOR THE INHIBITION OF THE CELL PROLIFERATION
  申请人：AstraZeneca AB

  公开号：EP1351958B1

  公开（公告）日：2004-06-16