4-(2-methylimidazo[1,2-a]pyridin-3-yl)-N-p-tolylpyrimidin-2-amine | 1203678-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 4-(2-methylimidazo[1,2-a]pyridin-3-yl)-N-p-tolylpyrimidin-2-amine
• 英文别名: 4-(2-methylimidazo[1,2-a]pyridin-3-yl)-N-(4-methylphenyl)pyrimidin-2-amine
• CAS: 1203678-26-5
• 化学式: C₁₉H₁₇N₅
• 分子量: 315.377
• InChiKey: OVJWJFJQVGNUPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-碘甲苯 、 4-(2-甲基咪唑并[1,2-a]吡啶-3-基)-2-嘧啶胺 在 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 为溶剂， 以80%的产率得到4-(2-methylimidazo[1,2-a]pyridin-3-yl)-N-p-tolylpyrimidin-2-amine
  参考文献：
  名称：

  Synthesis and cytotoxic activity of 2-methylimidazo[1,2-a]pyridine- and quinoline-substituted 2-aminopyrimidine derivatives

  摘要：

  A series of 2-methylimidazo[1,2-a]pyridine- and quinoline-substituted 2-aminopyrimidines derivatives were synthesized using a convenient synthetic route. We evaluate the isosteric replacement of methyl groups in 4-(2-methylimidazo[1,2-a]pyridin-3-yl)-N-p-tolylpyrimidin-2-amine (compound 1) by trifluoromethyl groups and the isosteric substitution of the 2-methylimidazo[1,2-a]pyridin-3-yl scaffold by quinolin-4-yl or quinolin-3-yl moieties. The replacement of hydrogen by fluorine does not affect notably the cytotoxic activity and CDK inhibitor activity in this series. Quinolin-4-yl-substituted compound, 8, presents cytotoxic activity and is most effective and selective against CDK1/CycA than against CDK2/CycB. Compound 11, which has a quinolin-3-yl moiety is CDK inhibitor but presents null cytotoxic activity. Quinolin-4-yl-substituted compounds constitute a new lead of cytotoxic and CDK inhibitor compounds from which more compelling and selective inhibitors can be designed. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.002

文献信息

• [EN] BMI-1 PROTEIN EXPRESSION MODULATORS<br/>[FR] MODULATEURS DE L'EXPRESSION DE LA PROTÉINE BMI-1
  申请人：PTC THERAPEUTICS INC

  公开号：WO2010002985A1

  公开（公告）日：2010-01-07

  The compounds, pharmaceutical compositions, and methods of using such compounds or compositions thereof described herein are useful for treating a disease modulated by B-cell specific Moloney murine leukemia virus integration site 1 (Bmi-1) protein expression.

  本文描述的化合物、药物组合物和使用这些化合物或组合物的方法对治疗由B细胞特异性Moloney小鼠白血病病毒整合位点1（Bmi-1）蛋白表达调节的疾病具有用处。
• BMI 1 PROTEIN EXPRESSION MODULATORS
  申请人：PTC Therapeutics, Inc.

  公开号：EP3111956A1

  公开（公告）日：2017-01-04

  The compounds, pharmaceutical compositions, and methods of using such compounds or compositions thereof described herein are useful for treating a disease modulated by B-cell specific Moloney murine leukemia virus integration site 1 (Bmi-1) protein expression.

  本文所述的化合物、药物组合物和使用此类化合物或其组合物的方法可用于治疗由 B 细胞特异性莫隆尼鼠白血病病毒整合位点 1（Bmi-1）蛋白表达调节的疾病。
• BMI-1 PROTEIN EXPRESSION MODULATORS
  申请人：PTC Therapeutics, Inc.

  公开号：EP2306836A1

  公开（公告）日：2011-04-13
• US8680113B2
  申请人：——

  公开号：US8680113B2

  公开（公告）日：2014-03-25