1-(1-环戊基-2-甲基-1H-咪唑-5-基)乙酮 | 600699-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(1-环戊基-2-甲基-1H-咪唑-5-基)乙酮
• 英文名称: 1-(2-methyl-3-propan-2-yl-imidazol-4-yl)ethanone
• 英文别名: 1-cyclopentyl-2-methyl-5-acetylimidazole；1-(3-cyclopentyl-2-methyl-imidazol-4-yl)ethanone；1-(3-cyclopentyl-2-methyl-3H-imidazole-4-yl)ethanone；1-(3-cyclopentyl-2-methylimidazol-4-yl)ethanone
• CAS: 600699-47-6
• 化学式: C₁₁H₁₆N₂O
• 分子量: 192.261
• InChiKey: XFYQJXUMNZFNQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-环戊基-2-甲基-1H-咪唑-5-基)乙酮 、 N,N-二甲基甲酰胺二甲基缩醛 在 二氯甲烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 以to give the title compound as a yellow solid (9.74 g)的产率得到(E)-1-(3-cyclopentyl-2-methyl-imidazol-4-yl)-3-dimethylamino-prop-2-en-1-one
  参考文献：
  名称：

  2-HETEROCYCLOAMINO-4-IMIDAZOLYLPYRIMIDINES AS AGENTS FOR THE INHIBITION OF CELL PROLIFERATION

  摘要：

  描述了具有细胞周期抑制活性的化合物，其化学式为（I）。

  公开号：

  US20090275567A1
• 作为产物：
  描述：

  N-环戊基-N-(5-甲基-1,2-恶唑-4-基)乙酰胺 在 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 3.0h， 生成 1-(1-环戊基-2-甲基-1H-咪唑-5-基)乙酮
  参考文献：
  名称：

  Imidazoles: SAR and development of a potent class of cyclin-dependent kinase inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.09.024

文献信息

• Imidazolyl-Pyrimidine Compounds for Use in the Treatment of Proliferative Disorders
  申请人：Andrews David

  公开号：US20080280906A1

  公开（公告）日：2008-11-13

  Compounds of formula (I): which possess cell-cycle inhibitory activity are described.

  描述了具有细胞周期抑制活性的化合物，其化学式为（I）。
• Imidazolyl-pyrimidine compounds for use in the treatment of proliferative disorders
  申请人：AstraZeneca AB

  公开号：EP2301928A1

  公开（公告）日：2011-03-30

  Compounds of formula (I): which possess cell-cycle inhibitory activity are described.

  式(I)化合物： 所述化合物具有细胞周期抑制活性。
• WO2007/138268
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/15064
  申请人：——

  公开号：——

  公开（公告）日：——
• Imidazole pyrimidine amides as potent, orally bioavailable cyclin-dependent kinase inhibitors
  作者：Clifford D. Jones、David M. Andrews、Andrew J. Barker、Kevin Blades、Kate F. Byth、M. Raymond V. Finlay、Catherine Geh、Clive P. Green、Marie Johannsen、Mike Walker、Hazel M. Weir

  DOI：10.1016/j.bmcl.2008.10.075

  日期：2008.12

  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.