9H-嘌呤-6-胺, n-环戊基- | 103626-36-4

• 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: 9H-嘌呤-6-胺, n-环戊基-
• 中文别名: 9H-嘌呤-6-胺,n-环戊基-
• 英文名称: N⁶-cyclopentyladenine
• 英文别名: N-cyclopentyl-9H-purin-6-amine；6-cyclopentylaminopurine；N-cyclopentyl-7H-purin-6-amine
• CAS: 103626-36-4
• 化学式: C₁₀H₁₃N₅
• mdl: MFCD11124690
• 分子量: 203.247
• InChiKey: LMWYJWNGVLKEDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9H-嘌呤-6-胺, n-环戊基- 在 disodium hydrogenphosphate 、 溴 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 8-bromo-N-cyclopentyl-3-propylpurin-6-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of disubstituted N6-cyclopentyladenine analogues

  摘要：

  Novel 3,8- and 8,9-disubstituted N(6)-cyclopentyladenine derivatives were synthesised in moderate overall yield from 6-chloropurine. The derivatives were made in an attempt to find a new neutral antagonist with high affinity for adenosine A(1) receptors. N(6)-Cyclopentyl-9-methyladenine (N-0840) was used as a lead compound. Binding affinities of the new analogues were determined for human adenosine A(1) and A(3) receptors. Their intrinsic activity was assessed in [35S]GTPgammaS binding experiments. Elongation of the 9-methyl of N-0840 to a 9-propyl substituent was very well tolerated. A 9-benzyl group, on the other hand, caused a decrease in adenosine A(1) receptor affinity. Next, the 8-position was examined in detail, and affinity was increased with appropriate substitution. Most derivatives were A(1)-selective and 20 of the new compounds (6-9, 15-21, 23-26, 28, 31, 33, 35, and 36) had higher adenosine A(1) receptor affinity than the reference substance, N-0840. Compound 31 (N(6)-cyclopentyl-8-(N-methylisopropylamino)-9-methyladenine, LUF 5608) had the highest adenosine A(1) receptor affinity, 7.7 nM. In the [35S]GTPgammaS binding experiments, derivatives 5, 14, 22, 23, 25, 26, 33 and 34 did not significantly change basal [35S]GTPgammaS binding, thus behaving as neutral antagonists. Moreover, four of these compounds (23, 25, 26, and 33) displayed a 4- to 10-fold increased adenosine A(1) receptor affinity (75-206 nM) compared to N-0840 (852 nM). In summary, we synthesised a range of N-0840 analogues with higher affinity for adenosine A(1) receptors. In addition, four new derivatives, LUF 5666 (23), LUF 5668 (25), LUF 5669 (26) and LUF 5674 (33), behaved as neutral antagonists when tested in [35S]GTPgammaS binding studies. Thus, these compounds have improved characteristics as neutral adenosine A(1) receptor antagonists.

  DOI：

  10.1016/j.bmc.2003.10.023
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 9H-嘌呤-6-胺, n-环戊基-
  参考文献：
  名称：

  通过Mitsunobu反应对腺嘌呤和腺苷的环外氮进行区域选择性烷基化

  摘要：

  以Mitsunobu反应为关键步骤，提出了一种新的合成途径来合成腺嘌呤的N 6-取代。在45°C下30分钟内，一系列伯醇和仲醇的收率都非常好，达到了极佳的水平，为传统的6-氯嘌呤亲核芳香族取代提供了温和的替代方法。通过将其应用于N 6，N 9-二取代的腺嘌呤的合成，包括有效的和选择性的A 1腺苷受体激动剂N 6-环戊基腺苷，进一步证明了该方案的实用性。

  DOI：

  10.1016/j.tetlet.2010.03.103

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] COMPOUNDS FOR IMPROVING MRNA SPLICING<br/>[FR] COMPOSÉS POUR AMÉLIORER L'ÉPISSAGE DE L'ARNM
  申请人：GEN HOSPITAL CORP

  公开号：WO2016115434A1

  公开（公告）日：2016-07-21

  Provided herein are compounds useful for improving mRNA splicing in a cell. Exemplary compounds provided herein are useful for improving mRNA splicing in genes comprising at least one exon ending in the nucleotide sequence CAA. Methods for preparing the compounds and methods of treating diseases of the central nervous system are also provided.

  本文提供了一些有助于改善细胞内mRNA剪接的化合物。本文提供的示例化合物有助于改善包含至少一个以核苷酸序列CAA结尾的外显子的基因的mRNA剪接。还提供了制备这些化合物的方法以及治疗中枢神经系统疾病的方法。
• Structural insights on the molecular recognition patterns between N6-substituted adenines and N-(aryl-methyl)iminodiacetate copper(II) chelates
  作者：Alicia Domínguez-Martín、Ángel García-Raso、Catalina Cabot、Duane Choquesillo-Lazarte、Inmaculada Pérez-Toro、Antonio Matilla-Hernández、Alfonso Castiñeiras、Juan Niclós-Gutiérrez

  DOI：10.1016/j.jinorgbio.2013.02.002

  日期：2013.10

  p-tolyl in MEBIDA and furfuryl in FurIDA) whereas HBAP, HCy5ade, HCy6ade and HdimAP are N6-substituted adenine derivatives with a N-benzyl, N-cyclopentyl, N-cyclohexyl or two N-methyl groups, respectively. Regardless of the molecular (1–4) or polymeric (5–6) nature of the studied compounds, the Cu(II) centre exhibits a type 4 + 1 coordination where the tridentate IDA-like chelators adopt a mer-conformation

  为了更好地理解N 6取代的腺嘌呤的金属结合模式，已通过单晶X射线衍射对六种新型三元Cu（II）配合物进行了结构表征：[Cu（NBzIDA）（HCy5ade）（H 2 O）] ·H 2 O（1），[Cu（NBzIDA）（HCy6ade）（H 2 O）]·H 2 O（2），[Cu（FurIDA）（HCy6ade）（H 2 O）]·H 2 O（3），[Cu（MEBIDA）（HBAP）（H 2 O）]·H 2 O（4），[Cu（FurIDA）（HBAP）] n（5）和[Cu（NBzIDA）（HdimAP）]·H 2 O} n（6）。在这些化合物中NBzIDA，FurIDA和MEBIDA被N-取代的具有非配位的芳基甲基侧链臂（苄基在NBzIDA，对甲苯基在MEBIDA和糠在FurIDA），而HBAP iminodiacetates，HCy5ade，HCy6ade和HdimAP是N 6 -分别具有N
• Inhibitors of MAPK/Erk Kinase
  申请人：Pinkerton B. Anthony

  公开号：US20070049591A1

  公开（公告）日：2007-03-01

  The present invention relates to compounds useful as inhibitors of MEK kinase and methods for the treatment or prevention of cellular proliferative disease states, such as conditions related to the hyperactivity of MEK, as well as diseases modulated by the MEK cascade.

  本发明涉及到作为MEK激酶抑制剂的化合物，以及用于治疗或预防细胞增殖性疾病状态的方法，例如与MEK过度活化有关的疾病，以及由MEK级联调控的疾病。
• [EN] ANHYDROUS POLYMORPHS OF (2R,3S,4R,5R)-5-(6-(CYCLOPENTYLAMINO)-9H-PURIN-9-YL)-3,4-DIHYDROXYTETRAHYDROFURAN-2-YL) } METHYL NITRATE AND PROCESSES OF PREPARATION THEREOF<br/>[FR] POLYMORPHES ANHYDRES DE NITRATE DE MÉTHYLE [(2R,3S,4R,5R)-5-(6- (CYCLOPENTYLAMINO)-9H-PURIN-9-YLE)-3,4-DIHYDROXYTETRAHYDROFURAN-2-YLE)] ET PROCESSUS DE PRÉPARATION DE CEUX-CI
  申请人：INOTEK PHARMACEUTICALS CORP

  公开号：WO2013112850A1

  公开（公告）日：2013-08-01

  The present invention provides novel anhydrous polymorph forms of 2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl nitrate (Compound A). The present invention also provides processes for preparation of the anhydrous polymorphic forms of compound A.

  本发明提供了2R，3S，4R，5R)-5-(6-(环戊基氨基)-9H-嘌呤-9-基)-3,4-二羟基四氢呋喃-2-基甲基硝酸盐（化合物A）的新型无水多晶形式。本发明还提供了制备化合物A无水多晶形式的方法。