2-[[9-(1-甲基乙基)-6-[(苯基甲基)氨基]-9H-嘌呤-2-基]氨基]-1-丁醇 | 186692-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-[[9-(1-甲基乙基)-6-[(苯基甲基)氨基]-9H-嘌呤-2-基]氨基]-1-丁醇
• 中文别名: 2-[[9-(1-甲基乙基)-6-[(苯甲基)氨基]-9H-嘌呤-2-基]氨基]-1-丁醇
• 英文名称: roscovitine
• 英文别名: (+/-)-Roscovitine；6-(benzylamino)-2-[(1-hydroxymethylpropyl)amino]-9-isopropylpurine；2-(1-ethyl-2-hydroxyethylamino)-N6-(benzyl)-9-isopropyladenine；RS-roscovitine；Seliciclib；roscovitin；2-[[9-(1-Methylethyl)-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-1-butanol；2-[[6-(benzylamino)-9-propan-2-ylpurin-2-yl]amino]butan-1-ol
• CAS: 186692-44-4
• 化学式: C₁₉H₂₆N₆O
• 分子量: 354.455
• InChiKey: BTIHMVBBUGXLCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  577.5±60.0 °C(Predicted)
• 密度：
  1.25

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  87.9
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  2-[[9-(1-甲基乙基)-6-[(苯基甲基)氨基]-9H-嘌呤-2-基]氨基]-1-丁醇 在 溴 、 一水合肼 作用下， 以 氯仿 为溶剂， 生成 2-(8-Amino-6-benzylamino-9-isopropyl-9H-purin-2-ylamino)-butan-1-ol
  参考文献：
  名称：

  2,6,8,9-Tetrasubstituted Purines as New CDK1 Inhibitors

  摘要：

  Purine inhibitors of cyclin-dependent kinases attract attention as potential anticancer drugs because their first representative roscovitine recently entered clinical trials. Although well described in terms of structure-activity relationships, we still present here a novel modification of the purine scaffold influencing their inhibitory properties. The introduced C-8 substituents, however, lowered the CDK inhibitory activity of roscovitine, whereas the antiproliferative potential of several derivatives remained high. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00632-2
• 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-[[9-(1-甲基乙基)-6-[(苯基甲基)氨基]-9H-嘌呤-2-基]氨基]-1-丁醇
  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

• Antisense modulation of cyclin-dependent kinase 4 expression
  申请人：Isis Pharmaceuticals Inc.

  公开号：US20040005567A1

  公开（公告）日：2004-01-08

  Antisense compounds, compositions and methods are provided for modulating the expression of cyclin-dependent kinase 4. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding cyclin-dependent kinase 4. Methods of using these compounds for modulation of cyclin-dependent kinase 4 expression and for treatment of diseases associated with expression of cyclin-dependent kinase 4 are provided.

  提供了用于调节细胞周期依赖性激酶4表达的反义化合物、组合物和方法。这些组合物包括针对编码细胞周期依赖性激酶4的核酸的反义化合物，特别是反义寡核苷酸。提供了利用这些化合物调节细胞周期依赖性激酶4表达并治疗与细胞周期依赖性激酶4表达相关疾病的方法。
• Acyl and sulfonyl derivatives of 6,9-disubstituted 2-(trans-1,4-diaminocyclohexyl)-purines and their use as antiproliferative agents
  申请人：——

  公开号：US20030069259A1

  公开（公告）日：2003-04-10

  The present invention is directed to acyl and sulfonyl derivatives of 6,9-disubstituted 2-(trans-1,4-diaminocyclohexyl)-purines and methods of using the same as antiproliferative agents or to prevent apoptosis.

  本发明涉及酰基和磺酰衍生物，其为6,9-二取代的2-(反-1,4-二氨基环己基)-嘌呤的衍生物，并且涉及使用它们作为抗增殖剂或预防细胞凋亡的方法。
• Palladium(II) oxalato complexes involving N6-(benzyl)-9-isopropyladenine-based N-donor carrier ligands: Synthesis, general properties, 1H, 13C and 15N{1H} NMR characterization and in vitro cytotoxicity
  作者：Pavel Štarha、Igor Popa、Zdeněk Trávníček

  DOI：10.1016/j.ica.2010.01.035

  日期：2010.4

  a series of seven palladium(II) oxalato (ox) complexes of the general formula [Pd(ox)(L 1–7 ) 2 ]· n H 2 O ( 1 – 7 ; n = 0 for 4 , 5 and 7 , ¾ for 1 and 2 , 1 for 6 , and 3 for 3 ). The compounds were characterized by elemental analysis, IR, Raman, 1 H, 13 C and 15 N 1 H} NMR spectroscopy, ESI+ mass spectrometry, molar conductivity and TG/DTA thermal analysis. The geometry of [Pd(ox)(L 2 ) 2 ] ( 2

  和3代表3）。通过元素分析，IR，拉曼，1 H，13 C和15 N 1 H} NMR光谱，ESI +质谱，摩尔电导率和TG / DTA热分析对化合物进行表征。[Pd（ox）（L 2）2]（2）的几何结构在理论上的B3LYP / 6-311G ∗ / LANL2DZ水平上得到了优化。配合物4 – 7代表第一批具有PdN 2 O 2供体的草酸钯（II）配合物，其中涉及基于嘌呤的高效细胞周期蛋白依赖性激酶（CDK）抑制剂（L 4–7）作为载体N-供体配体。通过MTT分析测试了选定的复合物1、3 – 5和7对人骨肉瘤（HOS）癌细胞的体外细胞毒活性。发现复合物5（IC 50 = 34.9μM）和复合物7（IC 50 = 39.2μM）的最高活性。13 C和15 N 1 H} NMR光谱，ESI +质谱，摩尔电导率和TG / DTA热分析。[Pd（ox）（L 2）2]（2）的几何结构在理论上的B3LYP
• [EN] FATTY ACID ANTICANCER DERIVATIVES AND THEIR USES<br/>[FR] DÉRIVÉS D'ACIDES GRAS ANTI-CANCÉREUX ET LEURS UTILISATIONS
  申请人：CATABASIS PHARMACEUTICALS INC

  公开号：WO2014204856A1

  公开（公告）日：2014-12-24

  The invention relates to fatty acid anticancer derivatives; compositions comprising an effective amount of a fatty acid anticancer derivative; and methods for treating or preventing cancer comprising the administration of an effective amount of a fatty acid anticancer derivative.

  这项发明涉及脂肪酸抗癌衍生物；包含有效量脂肪酸抗癌衍生物的组合物；以及治疗或预防癌症的方法，包括给予有效量脂肪酸抗癌衍生物的管理。
• Reduction of hair growth
  申请人：Botchkareva Natalia

  公开号：US20060135461A1

  公开（公告）日：2006-06-22

  Mammalian hair growth is reduced by topically applying a composition including a survivin inhibitor.

  哺乳动物的毛发生长通过局部涂抹包括生存素抑制剂的组合物而减少。