2-氯-9-异丙基-N-(4-甲氧基苄基)-9H-嘌呤-6-胺 | 203436-13-9

• 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-氯-9-异丙基-N-(4-甲氧基苄基)-9H-嘌呤-6-胺
• 英文名称: 2-chloro-6-(4-methoxybenzylamino)-9-isopropylpurine
• 英文别名: (2-chloro-9-isopropyl-9H-purin-6-yl)-(4-methoxybenzyl)-amine；2-chloro-9-isopropyl-N-(4-methoxybenzyl)-9H-purin-6-amine；2-chloro-6-[(4-methoxybenzyl)amino]-9-(2-propyl)purine；2-chloro-N-[(4-methoxyphenyl)methyl]-9-propan-2-ylpurin-6-amine
• CAS: 203436-13-9
• 化学式: C₁₆H₁₈ClN₅O
• 分子量: 331.805
• InChiKey: PDMSQJKBAMAEQE-UHFFFAOYSA-N

物化性质

• 沸点：
  483.1±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

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

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 |

反应信息

• 作为反应物：
  描述：

  2-氯-9-异丙基-N-(4-甲氧基苄基)-9H-嘌呤-6-胺 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 cis-[PtCl2(2-chloro-6-((4-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
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 6.0h， 生成 2-氯-9-异丙基-N-(4-甲氧基苄基)-9H-嘌呤-6-胺
  参考文献：
  名称：

  Synthesis and Pharmacophore Modelling of 2,6,9-Trisubstituted Purine Derivatives and Their Potential Role as Apoptosis-Inducing Agents in Cancer Cell Lines

  摘要：

  合成并研究了一系列2,6,9-三取代嘌呤衍生物，以探讨其作为抗肿瘤剂的潜在作用。通过三步合成程序获得了十二个化合物，其中微波辐射在一个关键步骤中发挥了重要作用。所有化合物都进行了体外评估，以确定其对细胞毒性的潜在影响，使用MTT法和流式细胞术分析四种癌细胞系和Vero细胞。与已知的有效抗癌药物依托泊苷相比，十二个化合物中有三个在四种癌细胞系中显示出良好的选择性，具有潜在的应用前景。初步的流式细胞术数据显示，上述化合物能诱导这些细胞的凋亡。每种癌细胞系的活性主要结构要求通过初步药效团模型进行了表征，该模型确定了芳香中心、氢受体/供体中心和疏水区域。这些特征与所测试化合物的细胞毒性活性一致。

  DOI：

  10.3390/molecules20046808

文献信息

• Kinase inhibitor scaffolds and methods for their preparation
  申请人：IRM LLC, a Delaware Limited Liability Company

  公开号：US20030191312A1

  公开（公告）日：2003-10-09

  General methods for the solution phase as well as solid phase synthesis of various substituted heteroaryls has been demonstrated. These substituted heteroaryls can be further elaborated by aromatic substitution with amines at elevated temperature or by anilines, boronic acids and phenols via palladium catalyzed cross-coupling reactions.

  已经展示了解决各种取代杂环烷基的溶液相和固相合成的一般方法。这些取代杂环烷基可以通过在高温下与胺发生芳香取代，或者通过钯催化的交叉偶联反应与苯胺、硼酸和酚进一步扩展。
• Expanding the diversity of purine libraries
  作者：Sheng Ding、Nathanael S Gray、Qiang Ding、Peter G Schultz

  DOI：10.1016/s0040-4039(01)01925-6

  日期：2001.12

  interest in the synthesis of purine derivatives due to the discovery of purine-derived ligands for a variety of nucleotide dependent enzymes. The majority of chemistry has focused on substitution of the purine core structure by alkylation at N9 and nucleophilic–aromatic substitution reactions at C2 and C6. Here we report the syntheses of aryl, N-aryl, O-aryl substituted purine libraries by the palladium-mediated

  近年来，由于发现了嘌呤衍生的用于多种核苷酸依赖性酶的配体，因此在嘌呤衍生物的合成中引起了人们的兴趣。大多数化学方法都集中在通过N9处的烷基化以及C2和C6处的亲核-芳族取代反应来取代嘌呤核心结构。这里，我们报告的芳基，的合成Ñ -芳基，ø -芳基取代的嘌呤库通过在C2位硼酸，苯胺或苯酚的钯介导的偶联，和铜（II）介导的Ñ -arylation与硼酸N9位置。此处描述的化学物质极大地扩展了我们引入不同功能并创建新嘌呤支架的能力。
• [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。
• Purine inhibitors of cyclin dependent kinase 2
  申请人：CV Therapeutics, Incorporation

  公开号：US05866702A1

  公开（公告）日：1999-02-02

  A 2,6,9-trisubstituted purine composition having the following formula: ##STR1## where X is a amino, oxo, thio, of sulfone moiety, R.sub.1 is a lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, cycloheteroalkyl, substituted cycloheteroalkyl, aryl, substituted aryl, heterocycle, hetaryl, substituted hetaryl, aralkyl, heteroaralkyl, heteroalkyl, alkyl alkenyl, alkyl alkynyl, alkyl cycloalkyl, or alkyl cycloheteroalkyl, each having from 1 to 20 carbon atoms; R.sub.2 is hydrogen, lower alkyl, substituted lower alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, heterocycle, hetaryl, substituted hetaryl, aralkyl, heteroaralkyl, heteroalkyl, alkyl alkenyl, alkyl alkynyl, alkyl cycloalkyl, or alkyl cycloheteroalkyl; and R.sub.3 is halogen, hydroxyl, thio, alkoxy, alkylthio, lower alkyl, --NR.sub.4 R.sub.5 or a component having the formula: ##STR2## wherein when R.sub.3 is 2-hydroxyethylamino and R.sub.2 is methyl, R.sub.1 -X is not amino, 3-methyl-2-butenylamino, benzylamino, or m-hydroxybenzyl-amino, when R.sub.3 is 2-hydroxyethylamino and R.sub.2 is isopropyl, R.sub.1 -X is not benzylamino, m-hydroxybenzylamino, or 3-methylbutylamino, when R.sub.3 is 2-hydroxyethylamino and R.sub.2 is 2-hydroxyethyl, R.sub.1 -X is not benzylamino and when R.sub.3 is selected from the group consisting of 2-propanol-2-methylamino and 2-dimethylaminoethylamino and R.sub.2 is methyl, then R.sub.1 -X is not benzylamino.

  具有以下公式的2,6,9-三取代嘌呤组成物：##STR1## 其中X是氨基，氧代基，硫代基或磺酰基，R.sub.1是低碳链烷基，取代低碳链烷基，环烷基，取代环烷基，环杂烷基，取代环杂烷基，芳基，取代芳基，杂环，杂芳基，取代杂芳基，芳基烷基，杂芳基烷基，杂基烷基，烷基烯烃基，烷基炔烃基，烷基环烷基或烷基环杂烷基，每个都有1到20个碳原子；R.sub.2是氢，低碳链烷基，取代低碳链烷基，环烷基，取代环烷基，芳基，取代芳基，杂环，杂芳基，取代杂芳基，芳基烷基，杂芳基烷基，杂基烷基，烷基烯烃基，烷基炔烃基，烷基环烷基或烷基环杂烷基；R.sub.3是卤素，羟基，硫代基，烷氧基，烷基硫代基，低碳链烷基，--NR.sub.4 R.sub.5或具有以下公式的组分：##STR2## 当R.sub.3是2-羟乙基氨基且R.sub.2是甲基时，R.sub.1 -X不是氨基，3-甲基-2-丁烯基氨基，苄基氨基或m-羟基苄基氨基；当R.sub.3是2-羟乙基氨基且R.sub.2是异丙基时，R.sub.1 -X不是苄基氨基，m-羟基苄基氨基或3-甲基丁基氨基；当R.sub.3是2-羟乙基氨基且R.sub.2是2-羟乙基时，R.sub.1 -X不是苄基氨基；当R.sub.3选自由2-异丙醇基-2-甲基氨基和2-二甲基氨基乙基氨基且R.sub.2是甲基时，R.sub.1 -X不是苄基氨基。
• Purine inhibitors of cyclin dependent kinase 2 and IkappaB-alpha
  申请人：Lum T. Robert

  公开号：US20050080261A1

  公开（公告）日：2005-04-14

  Compounds of the following formula are provided: In the Formula (I), R 1 is —X—R 1 ′; in which R 1 ′ is optionally substituted lower alkyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted heterocyclyl, and X is —NH—. R 2 is lower alkyl optionally substituted with one, two or three groups chosen from hydroxy, lower alkoxy, and halogen. And R 3 is —NR 4 R 5 ; in which R 4 is hydrogen and R 5 is lower alkyl substituted with amino; or (ii) R 4 and R 5 are both lower alkyl optionally substituted with one, two or three groups chosen from hydroxy and amino. It is to be understood that R 1 ′ is not cyclohexylmethyl, phenyl, substituted phenyl, benzyl, phenylethyl, or m-hydroxybenzyl. The compounds inhibit CDK-2 activity and are useful for treating disorders characterized by undesirable cell proliferation.

  提供以下公式的化合物：在公式（I）中，R1为—X—R1′；其中R1′为可选择取代的低烷基、可选择取代的芳基、可选择取代的杂芳基或可选择取代的杂环烷基，X为—NH—。R2为低烷基，可选择取代一个、两个或三个羟基、低烷氧基或卤素基。R3为—NR4R5；其中R4为氢，R5为取代氨基的低烷基；或（ii）R4和R5均为低烷基，可选择取代一个、两个或三个羟基和氨基。应理解R1′不是环己基甲基、苯基、取代苯基、苄基、苯乙基或间羟基苄基。这些化合物能够抑制CDK-2活性，并用于治疗具有不良细胞增殖特征的疾病。