N-benzyl-2-fluoro-9H-purin-6-amine | 3800-23-5

• 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: N-benzyl-2-fluoro-9H-purin-6-amine
• 英文别名: 6-benzylamino-2-fluoropurine；N-benzyl-2-fluoro-7H-purin-6-amine
• CAS: 3800-23-5
• 化学式: C₁₂H₁₀FN₅
• 分子量: 243.243
• InChiKey: TTYFSTRCKXBULP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-fluoro-9H-purin-6-amine 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 2,4-滴二甲胺盐 、 二甲基亚砜 、 正丁醇 为溶剂， 反应 96.0h， 生成 [(1S)-1-氰基-2-甲基丙基]氨基甲酸苄酯
  参考文献：
  名称：

  Design, synthesis and biological evaluation of 6-pyridylmethylaminopurines as CDK inhibitors

  摘要：

  The cyclin-dependent kinase (CDK) inhibitor seliciclib (1, CYC202) is in phase II clinical development for the treatment of cancer. Here we describe the synthesis of novel purines with greater solubility, lower metabolic clearance, and enhanced potency versus CDKs. These compounds exhibit novel selectivity profiles versus CDK isoforms. Compound alpha SbR-21 inhibits CDK2/cyclin E with IC(50) = 30 nM, CDK7-cyclin H with IC(50) = 1.3 mu M, and CDK9-cyclinT with IC(50) = 0.11 mu M; it (CCT68127) inhibits growth of HCT116 colon cancer cells in vitro with GI(50) = 0.7 mu M; and shows antitumour activity when dosed p.o. at 50 mg/kg to mice bearing HCT116 solid human tumour xenografts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.051
• 作为产物：
  描述：

  苄胺 在 tetrafluoroboric acid 、 三乙胺 、 sodium nitrite 作用下， 以 水 、 正丁醇 为溶剂， 反应 6.5h， 生成 N-benzyl-2-fluoro-9H-purin-6-amine
  参考文献：
  名称：

  嘌呤-2,6-二胺衍生物作为细胞周期蛋白依赖性激酶（CDK）抑制剂的设计，合成和初步生物学评估

  摘要：

  设计并合成了新型嘌呤-2,6-二胺衍生物，作为细胞周期蛋白依赖性激酶（CDK）抑制剂。根据初步的生物学评估，大多数化合物在CDK1酶分析中显示出良好的抑制活性，并且在某些肿瘤细胞系中显示出强大的抗增殖活性。尤其是，化合物11a（CDK1 /细胞周期蛋白B的IC 50 = 0.35 µmol / L，CDK2 /细胞周期蛋白A的IC 50 = 0.023 µmol / L）与Roscovitine（IC 50 = 2.54（CDK1 /细胞周期蛋白B和CD 50 /细胞周期蛋白A的IC 50 = 0.092 µmol / L）。

  DOI：

  10.1002/cjoc.201300420

文献信息

• Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)
  申请人：CHEN Han-Min

  公开号：US20140303112A1

  公开（公告）日：2014-10-09

  The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

  本发明涉及一种治疗疾病或病情的方法，该疾病或病情容易通过AMPK激活剂和公式化合物得到改善，这些化合物有助于激活AMP激活蛋白激酶（AMPK），并将这些化合物用于预防或治疗疾病，包括糖尿病前期、2型糖尿病、X综合症、代谢综合征和肥胖症。
• [EN] IMAGING AGENTS FOR NEURAL FLUX<br/>[FR] AGENTS D'IMAGERIE POUR FLUX NEURONAL
  申请人：GEN HOSPITAL CORP

  公开号：WO2016011394A1

  公开（公告）日：2016-01-21

  Provided herein are radiolabeled compounds useful for non-invasive imaging techniques. An exemplary radiolabeled compound provided herein is useful as a radiotracer for positron emission tomography. The present application also provides unlabeled compounds useful in methods of treating diseases of the central nervous system or disease of the peripheral nervous system. Methods for preparing radiolabeled compounds, preparing unlabeled compounds, and diagnostic methods using labeled or unlabeled compounds are also provided.

  本文提供了用于非侵入性成像技术的放射性标记化合物。本文提供的一种示例性放射性标记化合物可用作正电子发射断层扫描的放射示踪剂。本申请还提供了用于治疗中枢神经系统疾病或外周神经系统疾病的未标记化合物。还提供了制备放射性标记化合物、制备未标记化合物以及使用标记化或未标记化化合物的诊断方法。
• Methods for the synthesis of substituted purines
  申请人：IRM LLC, a Delaware Limited Liability Company

  公开号：US20030171583A1

  公开（公告）日：2003-09-11

  The invention provides general methods for preparing 2,9-, 2,6,9-, O 6 -aryl- and O 6 -alkyl-substituted purines in a combinatorial and traceless fashion. The methods involve, in some embodiments, Mitsunobu alkylation of 2-fluoro-6-phenylsulfenylpurine at N9 with alcohols in solution, followed by C2-capture of the purine core with a resin-bound amine and subsequent oxidation and displacement of the C6 sulfonyl group with amines and anilines.

  本发明提供了一种通用方法，以组合和无痕迹的方式制备2,9-, 2,6,9-, O6-芳基-和O6-烷基取代嘌呤。在某些实施例中，该方法涉及在溶液中使用醇对2-氟-6-苯基磺酰基嘌呤的N9进行三丁基膦酸酯烷基化，随后用树脂结合胺捕获嘌呤核心的C2，然后用胺和苯胺进行C6磺酰基基团的氧化和置换。
• PURINE DERIVATIVE COMPOUNDS FOR MEDICAL USE
  申请人：MANROS THERAPEUTICS

  公开号：US20150320753A1

  公开（公告）日：2015-11-12

  A method for treatment of disease by reduction in macrophages-mediated bacterial killing, including administration to patients in need a compound of formula (I): wherein A is N or CH; B is NO, or S; R 1 is H, (C 1 -C 4 )alkyl group, methyl(C 1 -C 6 )cycloalkyl group or (C 1 -C 6 )cycloalkyl group; R 2 is an aryl, arylmethyl group or methylheteroaryl group as methylpyridine and methylthiophene; R 3 is absent when B is O or S, or is H or (C 1 -C 4 )alkyl group when B is N; R 4 is (C 1 -C 5 )alkyl group or (C 1 -C 4 )cycloalkyl group, groups bearing a carboxylic acid group, and (C 1 -C 5 )alkyl group or (C 1 -C 4 )cycloalkyl substituted by hydroxyl group, halogen group or methoxy group, when B is N, R 3 and R 4 can together form a 5- or 6-membered heterocycle substituted by carboxylic acid group, substituted by a halogen atom, hydroxyl group, methoxy group or hydroxymethyl group, or pharmaceutically acceptable salt. Also provided are new compounds relating to this use.

  一种通过减少巨噬细胞介导的细菌杀伤治疗疾病的方法，包括向需要治疗的患者给予式(I)的化合物：其中A是N或CH；B是NO或S；R1是H，(C1-C4)烷基，甲基(C1-C6)环烷基或(C1-C6)环烷基；R2是芳基，芳基甲基基或甲基杂环芳基，如甲基吡啶和甲基噻吩；当B为O或S时，R3不存在，或者当B为N时，R3是H或(C1-C4)烷基；R4是(C1-C5)烷基或(C1-C4)环烷基，带有羧酸基团，以及(C1-C5)烷基或(C1-C4)环烷基被羟基基团，卤素基团或甲氧基团取代，当B为N时，R3和R4可以共同形成一个被羧酸基团取代的5-或6-成员杂环，在卤素原子，羟基基团，甲氧基团或羟甲基基团取代。还提供了与此用途相关的新化合物。
• [EN] COVALENT CDK2-BINDING COMPOUNDS FOR THERAPEUTIC PURPOSES<br/>[FR] COMPOSÉS DE LIAISON À CDK2 COVALENTS UTILISÉS À DES FINS THÉRAPEUTIQUES
  申请人：UMBRA THERAPEUTICS INC

  公开号：WO2022187693A1

  公开（公告）日：2022-09-09

  Heteroaryl sulfonyl compounds and compositions that have a CDK2 Recognition Moiety bound to an electrophile for the selective covalent modification of CDK2 to treat CDK2-mediated disorders are described.

  本文描述了具有CDK2识别基团结合到亲电体的杂环磺酰化合物和组合物，用于选择性共价修饰CDK2以治疗CDK2介导的疾病。