N-[2-(4-bromophenyl)ethyl]-2-chloro-9-propan-2-ylpurin-6-amine | 441056-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-[2-(4-bromophenyl)ethyl]-2-chloro-9-propan-2-ylpurin-6-amine
• CAS: 441056-06-0
• 化学式: C₁₆H₁₇BrClN₅
• 分子量: 394.701
• InChiKey: HNZMQFJARNCHAP-UHFFFAOYSA-N

物化性质

• 沸点：
  511.9±60.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(4-bromophenyl)ethyl]-2-chloro-9-propan-2-ylpurin-6-amine 、 trans-1,4-Diaminocyclohexane 以 乙醇 为溶剂， 生成 N2-((1r,4r)-4-aminocyclohexyl)-N6-(4-bromophenethyl)-9-isopropyl-9H-purine-2,6-diamine
  参考文献：
  名称：

  Biaryl purine derivatives as potent antiproliferative agents: Inhibitors of cyclin dependent kinases. Part I

  摘要：

  The introduction of an aryl ring onto the 4-position of the C-6 benzyl amino group of the Cdk inhibitor roscovitine (2), maintained the potent Cdk inhibition demonstrated by roscovitine (2) as well as greatly improving the antiproliferative activity. A series of C-6 biarylmethylamino derivatives was prepared addressing modifications on the C-6 biaryl rings, N-9 and C-2 positions to provide compounds that displayed potent cytotoxic activity against tumor cell lines. In particular, derivative 21h demonstrated a >750-fold improvement in the growth inhibition of HeLa cells compared to roscovitine (2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.025
• 作为产物：
  描述：

  2-碘代丙烷 、 N-[2-(4-bromophenyl)ethyl]-2-chloro-7H-purin-6-amine 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 生成 N-[2-(4-bromophenyl)ethyl]-2-chloro-9-propan-2-ylpurin-6-amine
  参考文献：
  名称：

  Biaryl purine derivatives as potent antiproliferative agents: Inhibitors of cyclin dependent kinases. Part I

  摘要：

  The introduction of an aryl ring onto the 4-position of the C-6 benzyl amino group of the Cdk inhibitor roscovitine (2), maintained the potent Cdk inhibition demonstrated by roscovitine (2) as well as greatly improving the antiproliferative activity. A series of C-6 biarylmethylamino derivatives was prepared addressing modifications on the C-6 biaryl rings, N-9 and C-2 positions to provide compounds that displayed potent cytotoxic activity against tumor cell lines. In particular, derivative 21h demonstrated a >750-fold improvement in the growth inhibition of HeLa cells compared to roscovitine (2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.025

文献信息

• Biaryl purine derivatives as potent antiproliferative agents: Inhibitors of cyclin dependent kinases. Part I
  作者：Michael P. Trova、Keith D. Barnes、Curt Barford、Travis Benanti、Mark Bielaska、Lori Burry、John M. Lehman、Christine Murphy、Harold O’Grady、Denise Peace、Susan Salamone、Jennifer Smith、Patricia Snider、Joseph Toporowski、Steven Tregay、Alison Wilson、Michael Wyle、Xiaozhang Zheng、Thomas D. Friedrich

  DOI：10.1016/j.bmcl.2009.10.025

  日期：2009.12

  The introduction of an aryl ring onto the 4-position of the C-6 benzyl amino group of the Cdk inhibitor roscovitine (2), maintained the potent Cdk inhibition demonstrated by roscovitine (2) as well as greatly improving the antiproliferative activity. A series of C-6 biarylmethylamino derivatives was prepared addressing modifications on the C-6 biaryl rings, N-9 and C-2 positions to provide compounds that displayed potent cytotoxic activity against tumor cell lines. In particular, derivative 21h demonstrated a >750-fold improvement in the growth inhibition of HeLa cells compared to roscovitine (2). (C) 2009 Elsevier Ltd. All rights reserved.