[1-[[6-[(4-Bromophenyl)methylamino]-9-propan-2-ylpurin-2-yl]amino]cyclopentyl]methanol | 294648-13-8

• 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: [1-[[6-[(4-Bromophenyl)methylamino]-9-propan-2-ylpurin-2-yl]amino]cyclopentyl]methanol
• CAS: 294648-13-8
• 化学式: C₂₁H₂₇BrN₆O
• 分子量: 459.389
• InChiKey: XTGFJAXMBITFCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  87.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1-[[6-[(4-Bromophenyl)methylamino]-9-propan-2-ylpurin-2-yl]amino]cyclopentyl]methanol 、 苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 18.0h， 生成 [1-[[6-[(4-Phenylphenyl)methylamino]-9-propan-2-ylpurin-2-yl]amino]cyclopentyl]methanol
  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：

  1-氨基-1-环戊基甲醇 、 N-(4-bromobenzyl)-2-chloro-9-isopropyl-9H-purin-6-amine 以 乙醇 为溶剂， 生成 [1-[[6-[(4-Bromophenyl)methylamino]-9-propan-2-ylpurin-2-yl]amino]cyclopentyl]methanol
  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.