N6-(2-phenylethyl)adenosine | 20125-39-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N6-(2-phenylethyl)adenosine
• 英文别名: N6-Phenylethyladenosine；N⁶-(2-phenylethyl)purine riboside；N-(2-phenylethyl)adenosine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-(phenethylamino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol；N⁶-phenethyl-adenosine；N6-(β-phenethyl)adenosine；N6-(2-phenethyl)-adenosine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(2-phenylethylamino)purin-9-yl]oxolane-3,4-diol
• CAS: 20125-39-7
• 化学式: C₁₈H₂₁N₅O₄
• 分子量: 371.396
• InChiKey: LGZYEDZSPHLISU-SCFUHWHPSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  723.5±70.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)
• 溶解度：
  0.1 M NaOH：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N6-(2-phenylethyl)adenosine 在 Proton Sponge 、 三氯氧磷 、 吡啶 、 N,N-二丁基丁烷-1-胺,磷酸 作用下， 以 various solvent(s) 为溶剂， 生成 N6-(2-phenethyl)-adenosine-5'-O-diphosphate
  参考文献：
  名称：

  A Molecular Target for Suppression of the Evolution of Antibiotic Resistance:  Inhibition of the Escherichia coli RecA Protein by N⁶-(1-Naphthyl)-ADP

  摘要：

  We report that N-6-(1-naphthyl)-ADP (1) inhibits the Escherichia coli RecA protein in vitro. A novel rapid screen identified 1 as a potent inhibitor of RecA nucleoprotein filament formation, and further characterization established 1 as an ATP-competitive inhibitor of RecA-catalyzed ATP hydrolysis. 1 and other inhibitors of RecA activities represent a new approach for understanding the molecular targets and pathways involved in the evolution of antibiotic resistance in bacteria.

  DOI：

  10.1021/jm050113z
• 作为产物：
  描述：

  2’,3’,5’-三乙酰肌苷 在 4-二甲氨基吡啶 、 氨 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 37.34h， 生成 N6-(2-phenylethyl)adenosine
  参考文献：
  名称：

  α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5′-Nucleotidase (CD73) Inhibitors

  摘要：

  ecto-5'-Nucleotidase (eN, CD73) catalyzes the hydrolysis of extracellular AMP to adenosine. eN inhibitors have potential for use as cancer therapeutics. The eN inhibitor alpha,beta-methylene-ADP (AOPCP, adenosine-5'-O-[(phosphonomethyl)phosphonic acid]) was used as a lead structure, and derivatives modified in various positions were prepared. Products were tested at rat recombinant eN. 6-(Ar)alkylamino substitution led to the largest improvement in potency. N-6-Monosubstitution was superior to symmetrical N-6,N-6-disubstitution. The most potent inhibitors were N-6-(4chlorobenzyl)-(10l, PSB-12441, K-i 7.23 n.M), N-6-phenylethyl(10h, PSB-12425, K-i 8.04 nM), and N-6-benzyl-adenosine-5'-O[(phosphonomethyl)phosphonic acid] (10g, PSB-12379, K-i 9.03 nM). Replacement of the 6-NH group in 10g by 0 (10q, PSB-12431) or S (10r, PSB-12553) yielded equally potent inhibitors (10q, 9.20 nM; 10r, 9.50 aM). Selected compounds investigated at the human enzyme did not show species differences; they displayed high selectivity versus other ecto-nudeotidases and ADP-activated P2Y receptors. Moreover, high metabolic stability was observed. These compounds represent the most potent eN inhibitors described to date.

  DOI：

  10.1021/acs.jmedchem.5b00802

文献信息

• Anti-HCV nucleoside derivatives
  申请人：——

  公开号：US20030008841A1

  公开（公告）日：2003-01-09

  The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

  本发明涉及新颖和已知的嘌呤和嘧啶核苷衍生物，已发现这些衍生物对丙型肝炎病毒（HCV）具有活性。本发明声明利用这些衍生物治疗HCV感染，以及本文所披露的新颖核苷衍生物。
• Inhibitors of DNA Methyltransferase
  申请人：Wahhab Amal

  公开号：US20080132525A1

  公开（公告）日：2008-06-05

  The invention relates to the inhibition of DNA methyltransferase isoforms DNMT1 and DNMT3b2. The invention provides compounds and methods for inhibiting DNMT1 and DNMT3b2.

  这项发明涉及抑制DNA甲基转移酶亚型DNMT1和DNMT3b2。该发明提供了用于抑制DNMT1和DNMT3b2的化合物和方法。
• N6-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity
  作者：Roberta Ottria、Silvana Casati、Erika Baldoli、Jeanette A.M. Maier、Pierangela Ciuffreda

  DOI：10.1016/j.bmc.2010.09.030

  日期：2010.12

  between structure and biological activity of iPA. The structures of the compounds were confirmed by standard studies of 1H NMR, MS and elemental analysis. These molecules were then evaluated for their anti-proliferative activity on bladder cancer cells. We found that some of these compounds possess anti-proliferative activity but have no effect on cell invasion and metalloprotease activity.

  合成了一系列在N 6位上不同取代的腺苷类似物，以继续我们对iPA的结构与生物学活性之间关系的研究。化合物的结构通过1 H NMR，MS和元素分析的标准研究确认。然后评估这些分子对膀胱癌细胞的抗增殖活性。我们发现其中一些化合物具有抗增殖活性，但对细胞侵袭和金属蛋白酶活性没有影响。
• Modification of the length and structure of the linker of N6-benzyladenosine modulates its selective antiviral activity against enterovirus 71
  作者：Mikhail S. Drenichev、Vladimir E. Oslovsky、Liang Sun、Aloys Tijsma、Nikolay N. Kurochkin、Vitali I. Tararov、Alexander O. Chizhov、Johan Neyts、Christophe Pannecouque、Pieter Leyssen、Sergey N. Mikhailov

  DOI：10.1016/j.ejmech.2016.01.036

  日期：2016.3

  high yields. Analysis of the structure-activity relationship clearly shows that the optimal size of the linker is limited to 2 or 3 atoms (compounds 4–7). 2′-Deoxyadenosine derivatives did not elicit any inhibitory or cytotoxic effect, while 5′-deoxynucleosides still induced some cell protective antiviral activity. Based on these observations, it can be hypothesized that there may be another mechanism

  最近，我们证明了N 6-异戊烯基腺苷，一种细胞分裂素核苷，对人肠病毒71的复制具有有效的选择性抗病毒作用。本研究致力于另一种天然化合物N 6-苄基腺苷的结构优化。我们主要研究腺嘌呤和苯环之间连接基的大小和性质，以及D-核糖残基的必要性。制备了30多种N 6-苄基腺苷类似物，并评估了它们的抗病毒特性。两种主要的制备方法：N 6-乙酰基-2'，3'，5'-tri- O-乙酰基腺苷可以在碱促进条件下通过烷基卤或在Mitsunobu反应中通过醇进行区域选择性烷基化。在室温下用4 M PrNH 2在MeOH中的溶液脱酰1天后，以高总收率获得所需产物。对结构-活性关系的分析清楚地表明，连接子的最佳尺寸限于2或3个原子（化合物4 – 7）。2'-脱氧腺苷衍生物没有引起任何抑制或细胞毒性作用，而5'-脱氧核苷仍然诱导了某些细胞保护性抗病毒活性。基于这些观察，可以假设除了可能的5'-三磷酸化继之以对RNA合
• N.sup.6 -substituted adenosines
  申请人：Schering Aktiengesellschaft

  公开号：US03983104A1

  公开（公告）日：1976-09-28

  Novel N.sup.6 -substituted adenosines and a novel process for the preparation of N.sup.6 -substituted adenosines from 6-trialkylsiloxypurine derivatives. The derivatives are reacted in the presence of a tertiary base or a Lewis acid with ammonia or an amine of the formula HNR.sub.1 R.sub.2, wherein R.sub.1 and R.sub.2 are the same or different represent hydrogen, alkyl of 1-6 carbon atoms, aralkyl or 7 to 10 carbon atoms unsubstituted or substituted with hydroxy or alkoxy with 1-4 carbon atoms, aryl unsubstituted or substituted with hydroxy or alkoxy with 1 to 4 carbon atoms, a heterocyclic ring of 4 to 7 members, containing a total of 1-3 hetero atoms which can be nitrogen, oxygen or sulfur; or when R.sub.1 is hydrogen R.sub.2 is hydroxyl, amino, alkyl of 1-4 carbon atoms substituted in the terminal position with a mono- or dialkylamino group, containing 1-4 carbon atoms in each alkyl group, or mono- or bicyclic heterocyclic group of 5-10 members, containing a total of 1-3 hetero atoms, which can be nitrogen, oxygen and sulfur, or R.sub.1 and R.sub.2, together with the N-atom, collectively represent a heteromonocyclic ring of 4-7 members containing a total of 1-3 hetero atoms which, in addition to the nitrogen atom, can be nitrogen, oxygen or sulfur, unsubstituted or substituted by an alkyl group with 1-4 carbon atoms. The compounds of the invention have valuable biological properties such as cytokinins, etc.

  N.sup.6-取代腺苷类新化合物及从6-三烷基硅氧基嘌呤衍生物制备N.sup.6-取代腺苷类化合物的新方法。这些衍生物在三级碱或Lewis酸存在下与氨或HNR.sub.1 R.sub.2（其中R.sub.1和R.sub.2相同或不同，代表氢、1-6碳原子的烷基、7-10碳原子的芳基或未取代或取代的含有氢氧基或1-4碳原子的烷氧基的芳基，未取代或取代的含有氢氧基或1-4碳原子的烷氧基的芳基，含有1-3个杂原子的4-7环的杂环，这些杂原子可以是氮、氧或硫；或者当R.sub.1为氢时，R.sub.2为羟基、氨基、1-4碳原子的末端取代为单烷基氨基团的烷基，每个烷基团中含有1-4碳原子，或含有1-3个杂原子的5-10环的单烷基或双环杂环基，这些杂原子可以是氮、氧和硫，或R.sub.1和R.sub.2与N原子一起共同代表含有1-3个杂原子的4-7环的杂单环环，除氮原子外，这些杂原子可以是氮、氧或硫，未取代或取代为含有1-4碳原子的烷基。该发明的化合物具有诸如细胞激素等有价值的生物学性质。