2-chloro-6-((2-methoxybenzyl)amino)-9-isopropylpurine | 932748-80-6

• 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-chloro-6-((2-methoxybenzyl)amino)-9-isopropylpurine
• 英文别名: 2-chloro-6-(2-methoxybenzyl)amino-9-isopropylpurine；2-chloro-N6-(2-methoxybenzyl)-9-isopropyladenine；2-chloro-N-[(2-methoxyphenyl)methyl]-9-propan-2-ylpurin-6-amine
• CAS: 932748-80-6
• 化学式: C₁₆H₁₈ClN₅O
• 分子量: 331.805
• InChiKey: XEFUFVXONNYENZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  64.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-6-((2-methoxybenzyl)amino)-9-isopropylpurine 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 trans-[PtCl2(2-chloro-6-((2-methoxybenzyl)amino)-9-isopropylpurine)2]
  参考文献：
  名称：

  Preparation and cis-to-trans transformation study of square-planar [Pt(Ln)2Cl2] complexes bearing cytokinins derived from 6-benzylaminopurine (Ln) by view of NMR spectroscopy and X-ray crystallography

  摘要：

  Mononuclear, square-planar platinum(II) complexes involving derivatives of aromatic cytokinins as the ligands, and having the general formula cis-[Pt(L-n)(2)Cl-2] (1-3) and trans-[Pt(L-n)(2)Cl-2] (4-6), where n = 13, L-1 = 2-chloro-6-(benzylamino)-9-isopropylpurine, L-2 = 2-chloro-6-[(4-methoxybenzyl)amino]-9-isopropylpurine and L-3 = 2-chloro-6-[(2-methoxybenzyl)-amino]-9-isopropylpurine, have been synthesized and characterized by elemental analysis, MALDI-TOF mass, FT IR, H-1, C-13, N-15 and Pt-195 NMR spectral measurements. Dynamic cis-to-trans isomerization process of complex 1 in N,N'-dimethylformamide (DMF) has been investigated by means of multinuclear NMR spectroscopy. The solid-state structures of 1, 4 center dot (DMF)(2), and 5 have been determined by single crystal X-ray analysis. X-ray structures revealed that the heterocyclic ligands are coordinated to platinum via nitrogen atom N(7) in all the complexes studied. In vitro cytotoxicity of the prepared complexes against MCF7, G361, K562, and HOS has been evaluated. Owing to low solubility of the complexes in water, the cytotoxicity has been only tested up to 5 mu M concentration. Unfortunately, all complexes have been found to be non-cytotoxic in the accessible concentration range.

  DOI：

  10.1016/j.poly.2008.05.021

文献信息

• 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
• In Vitro Cytotoxic‐Active Platinum(II) Complexes Derived from Carboplatin and Involving Purine Derivatives
  作者：Lukáš Dvořák、Igor Popa、Pavel Štarha、Zdeněk Trávníček

  DOI：10.1002/ejic.201000322

  日期：2010.8

  C, 15 N and 195 Pt) spectroscopy. Based on the results of these techniques, it can be concluded that the central Pt II atom of the complexes 1-6 is coordinated to two oxygen atoms originating from the cyclobutane-1,1-dicarboxylate group and to two nitrogen atoms from two HL n molecules, that is, having a PtN 2 O 2 donor set. Detailed multinuclear and two-dimensional NMR studies indicated the N-7 atom

  六种铂 (II) 配合物的通式为 [Pt(cbdc)-(HL n ) 2 ] (1-6; cbdc = 环丁烷-1,1-二羧酸酯和 HL 1 -HL 6 = 苄基取代的 6-苄氨基-已经通过 [Pt(cbdc)(dmso) 2 ] 与相应的 HL n 化合物反应合成了 2-氯-9-异丙基嘌呤衍生物。制备的配合物通过元素分析和 FTIR、拉曼和 NMR（ 1 H、 13 C、 15 N 和 195 Pt）光谱表征。基于这些技术的结果，可以得出结论，配合物 1-6 的中心 Pt II 原子与来自 1,1-二羧酸环丁烷基团的两个氧原子和来自两个 HL n 的两个氮原子配位分子，即具有 PtN 2 O 2 供体组。详细的多核和二维 NMR 研究表明 N-7 原子是嘌呤衍生物的配位位点。[Pt(cbdc)(dmso)-(HL 7 )]·H 2 O (7a·H 2 O) 中间体 [HL 7 = 2-氯-
• [EN] CYCLOBUTAN-1,1 -DICARBOXYLATO COMPLEXES OF PLATINUM WITH N6-BENZYLADENINE DERIVATIVES, METHOD OF THEIR PREPARATION AND APPLICATION OF THESE COMPLEXES AS DRUGS IN ANTITUMOUR THERAPY<br/>[FR] COMPLEXES CYCLOBUTANE-1,1-DICARBOXYLATO DE PLATINE AVEC DES DÉRIVÉS DE N6-BENZYLADÉNINE, LEUR PROCÉDÉ DE PRÉPARATION ET LEUR APPLICATION EN TANT QUE MÉDICAMENTS DANS UN TRAITEMENT ANTITUMORAL
  申请人：UNIV PALACKEHO

  公开号：WO2011029415A1

  公开（公告）日：2011-03-17

  Cyclobutane-1,1-dicarboxylato complexes of platinum in the oxidation state +II and their crystal-solvates including the structural motif I or having the general formula Il expressed by the structural formula [Pt(cbdc)(L)2] Il or the general formula III expressed by the structural formula [Pt(cbdc)(L)(L')] III, where the symbols L and L' stand for N6-benzyladenine derivatives of the general formula IV bound to the platinum atom of the basic motif V through any adenine nitrogen atom independently chosen from the N1, N3, N6, N7 or N9 atoms, depending on the substitution rate of the molecules IV, where the substituents R1, R2 a R3 are independently chosen from the group of: hydrogen atom, halogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, cycloalkenyl, substituted cycloalkenyl, cycloheteroalkenyl, substituted cycloheteroalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, functional group and N-R'R" group, where R' and R" independently symbolize hydrogen atom, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, cycloalkenyl, substituted cycloalkenyl, cycloheteroalkenyl, substituted cycloheteroalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl and functional group.

  铂的氧化态为+II的环丁二酸-1,1-二羧酸配合物及其晶体溶剂包括结构基团I或具有由结构式[Pt(cbdc)(L)2] II表示的一般式Il或由结构式[Pt(cbdc)(L)(L')] III表示的一般式III，其中符号L和L'代表通式IV的N6-苄腺嘌呤衍生物，通过任何腺嘌呤氮原子独立选择自N1、N3、N6、N7或N9原子与基本基团V的铂原子结合，取决于分子IV的取代率，其中取代基R1、R2和R3独立选择自以下组中的: 氢原子、卤素、烷基、取代烷基、烯基、取代烯基、炔基、取代炔基、环烷基、取代环烷基、环杂烷基、取代环杂烷基、环烯基、取代环烯基、环杂烯基、取代环杂烯基、芳基、取代芳基、杂芳基、取代杂芳基、功能基团和N-R'R"基团，其中R'和R"独立表示氢原子、烷基、取代烷基、烯基、取代烯基、炔基、取代炔基、环烷基、取代环烷基、环杂烷基、取代环杂烷基、环烯基、取代环烯基、环杂烯基、取代环杂烯基、芳基、取代芳基、杂芳基、取代杂芳基和功能基团。
• [EN] OXALATO COMPLEXES OF PLATINUM<br/>[FR] COMPLEXES OXALATO-PLATINE
  申请人：UNIV PALACKEHO

  公开号：WO2010121575A1

  公开（公告）日：2010-10-28

  Oxalato complexes of platinum in the oxidation state +II and their crystal-solvates including the structural motif (I) or having the general formula (II) expressed by the structural formula [Pt(L)2(ox)] (II) or the general formula (III) expressed by the structural formula [Pt(L)(L')(ox)] (III), where the symbols L and L' stand for N6- benzyladenine derivatives of the general formula (IV) bound to the platinum atom of the basic motif (V) through any adenine nitrogen atom independently chosen from the N1, N3, N6, N7 or N9 atoms, depending on the substitution rate of the molecules (IV), where the substituents R1, R2 a R3 are independently chosen from the group of: hydrogen atom, halogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, cycloalkenyl, substituted cycloalkenyl, cycloheteroalkenyl, substituted cycloheteroalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, functional group and N-R'R" group, where R' and R" independently symbolize hydrogen atom, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, cycloalkenyl, substituted cycloalkenyl, cycloheteroalkenyl, substituted cycloheteroalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl and functional group.
• Preparation and cis-to-trans transformation study of square-planar [Pt(Ln)2Cl2] complexes bearing cytokinins derived from 6-benzylaminopurine (Ln) by view of NMR spectroscopy and X-ray crystallography
  作者：Lucie Szüčová、Zdeněk Trávníček、Igor Popa、Jaromír Marek

  DOI：10.1016/j.poly.2008.05.021

  日期：2008.8

  Mononuclear, square-planar platinum(II) complexes involving derivatives of aromatic cytokinins as the ligands, and having the general formula cis-[Pt(L-n)(2)Cl-2] (1-3) and trans-[Pt(L-n)(2)Cl-2] (4-6), where n = 13, L-1 = 2-chloro-6-(benzylamino)-9-isopropylpurine, L-2 = 2-chloro-6-[(4-methoxybenzyl)amino]-9-isopropylpurine and L-3 = 2-chloro-6-[(2-methoxybenzyl)-amino]-9-isopropylpurine, have been synthesized and characterized by elemental analysis, MALDI-TOF mass, FT IR, H-1, C-13, N-15 and Pt-195 NMR spectral measurements. Dynamic cis-to-trans isomerization process of complex 1 in N,N'-dimethylformamide (DMF) has been investigated by means of multinuclear NMR spectroscopy. The solid-state structures of 1, 4 center dot (DMF)(2), and 5 have been determined by single crystal X-ray analysis. X-ray structures revealed that the heterocyclic ligands are coordinated to platinum via nitrogen atom N(7) in all the complexes studied. In vitro cytotoxicity of the prepared complexes against MCF7, G361, K562, and HOS has been evaluated. Owing to low solubility of the complexes in water, the cytotoxicity has been only tested up to 5 mu M concentration. Unfortunately, all complexes have been found to be non-cytotoxic in the accessible concentration range.