2-({6-[(2-hydroxy-5-methylbenzyl)amino]-9-(isopropyl)-9H-purin-2-yl}amino)butan-1-ol | 1222186-58-4

• 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: 2-({6-[(2-hydroxy-5-methylbenzyl)amino]-9-(isopropyl)-9H-purin-2-yl}amino)butan-1-ol
• 英文别名: 2-(((2-((1-Hydroxybutan-2-yl)amino)-9-isopropyl-9H-purin-6-yl)amino)methyl)-4-methylphenol；2-[[[2-(1-hydroxybutan-2-ylamino)-9-propan-2-ylpurin-6-yl]amino]methyl]-4-methylphenol
• CAS: 1222186-58-4
• 化学式: C₂₀H₂₈N₆O₂
• 分子量: 384.481
• InChiKey: KWXOHZOEEBOAEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,6-二氯嘌呤 在 potassium carbonate 、 三乙胺 作用下， 以 二甲基亚砜 、 正丁醇 为溶剂， 生成 2-({6-[(2-hydroxy-5-methylbenzyl)amino]-9-(isopropyl)-9H-purin-2-yl}amino)butan-1-ol
  参考文献：
  名称：

  The first iron(III) complexes with cyclin-dependent kinase inhibitors: Magnetic, spectroscopic (IR, ES+ MS, NMR, 57Fe Mössbauer), theoretical, and biological activity studies

  摘要：

  The first Fe-III complexes 1-6 with cyclin-dependent kinase (CDK) inhibitors of the type [Fe(L-n)Cl-3]center dot nH(2)O (n = 0 for 1, 1 for 2, 2 for 3-6; L-1-L-6 = C2- and phenyl-substituted CDK inhibitors derived from 6-benzyl-amino-9-isopropylpurine), have been synthesized and characterized by elemental analysis, IR, Fe-57 Mossbauer, H-1 and C-13 NMR, and ES+ mass spectroscopies, conductivity and magnetic susceptibility measurements, and thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The study revealed that the compounds are mononuclear, tetrahedral high-spin (S = 5/2) Fe-III complexes with an admixture of an S = 3/2 spin state originating probably from five-coordinated Fe-III ions either connecting with a bidentate coordination mode of the CDK inhibitor ligand or relating to the possibility that one crystal water molecule enters the coordination sphere of the central atom in a portion of molecules of the appropriate complex. Nearly spin-only value of the effective magnetic moment (5.82 mu(eff)/mu(B)) was determined for compound 1 due to absence of crystal water molecule(s) in the structure of the complex. Based on NMR data and DFT calculations, we assume that the appropriate organic ligand is coordinated to the Fe-III ion through the N7 atom of a purine moiety. The cytotoxicity of the complexes was tested in vitro against selected human cancer cell lines (G-361, HOS, K-562 and MCF-7) along with the ability to inhibit the CDK2/cyclinE kinase. The best cytotoxicity (IC50: 4-23 mu M) and inhibition activity (IC50: 0.02-0.09 mu M) results have been achieved in the case of complexes 2-4, and complexes 3,4 and 6, respectively. In addition, the X-ray structure of 2-chloro-6-benzylamino-9-isopropylpurine, i.e. a precursor for the preparation of L-1, L-4 and L-5, is also described. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2009.12.002

文献信息

• US8492391B2
  申请人：——

  公开号：US8492391B2

  公开（公告）日：2013-07-23
• The first iron(III) complexes with cyclin-dependent kinase inhibitors: Magnetic, spectroscopic (IR, ES+ MS, NMR, 57Fe Mössbauer), theoretical, and biological activity studies
  作者：Zdeněk Trávníček、Igor Popa、Michal Čajan、Radek Zbořil、Vladimír Kryštof、Jiří Mikulík

  DOI：10.1016/j.jinorgbio.2009.12.002

  日期：2010.4

  The first Fe-III complexes 1-6 with cyclin-dependent kinase (CDK) inhibitors of the type [Fe(L-n)Cl-3]center dot nH(2)O (n = 0 for 1, 1 for 2, 2 for 3-6; L-1-L-6 = C2- and phenyl-substituted CDK inhibitors derived from 6-benzyl-amino-9-isopropylpurine), have been synthesized and characterized by elemental analysis, IR, Fe-57 Mossbauer, H-1 and C-13 NMR, and ES+ mass spectroscopies, conductivity and magnetic susceptibility measurements, and thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The study revealed that the compounds are mononuclear, tetrahedral high-spin (S = 5/2) Fe-III complexes with an admixture of an S = 3/2 spin state originating probably from five-coordinated Fe-III ions either connecting with a bidentate coordination mode of the CDK inhibitor ligand or relating to the possibility that one crystal water molecule enters the coordination sphere of the central atom in a portion of molecules of the appropriate complex. Nearly spin-only value of the effective magnetic moment (5.82 mu(eff)/mu(B)) was determined for compound 1 due to absence of crystal water molecule(s) in the structure of the complex. Based on NMR data and DFT calculations, we assume that the appropriate organic ligand is coordinated to the Fe-III ion through the N7 atom of a purine moiety. The cytotoxicity of the complexes was tested in vitro against selected human cancer cell lines (G-361, HOS, K-562 and MCF-7) along with the ability to inhibit the CDK2/cyclinE kinase. The best cytotoxicity (IC50: 4-23 mu M) and inhibition activity (IC50: 0.02-0.09 mu M) results have been achieved in the case of complexes 2-4, and complexes 3,4 and 6, respectively. In addition, the X-ray structure of 2-chloro-6-benzylamino-9-isopropylpurine, i.e. a precursor for the preparation of L-1, L-4 and L-5, is also described. (C) 2009 Elsevier Inc. All rights reserved.