6-(3-methyl-2-butenylamino)-9-(2'-deoxy-β-D-ribofuranosyl)purine | 25775-85-3

• 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: 6-(3-methyl-2-butenylamino)-9-(2'-deoxy-β-D-ribofuranosyl)purine
• 英文别名: N⁶-(3-methyl-2-buten-1-yl)-2'-deoxyadenosine；N⁶-(2-Isopentenyl)-2'-deoxyadenosine；N⁶-(3-methyl-but-2-enyl)-2'-deoxy-adenosine；6-(3-methyl-2-butenylamino-9-(2-deoxy-β-D-ribofuranosyl)-purine；(2R,3S,5R)-2-(Hydroxymethyl)-5-(6-((3-methylbut-2-en-1-yl)amino)-9H-purin-9-yl)tetrahydrofuran-3-ol；(2R,3S,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolan-3-ol
• CAS: 25775-85-3
• 化学式: C₁₅H₂₁N₅O₃
• 分子量: 319.363
• InChiKey: RQJJSCGVSYFLOS-QJPTWQEYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  609.7±65.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3',5'-di-O-acetyl-2'-deoxyadenosine 在 ammonium hydroxide 、 barium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 192.0h， 生成 6-(3-methyl-2-butenylamino)-9-(2'-deoxy-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Regioselective 1-N-Alkylation and Rearrangement of Adenosine Derivatives

  摘要：

  Several methods for the preparation of some N-6-substituted adenosines based on selective 1-N-alkylation with subsequent Dimroth rearrangement were developed. The proposed methods seem to be effective for the preparation of natural N-6-isopentenyl- and N-6-benzyladenosines, which are known to possess pronounced biological activities. Direct 1-N-alkylation of 2 ',3 ',5 '-tri-O-acetyladenosine and 3 ',5 '-di-O-acetyl-2 '-deoxyadenosine with alkyl halides in N,N-dimethylformamide (DMF) in the presence of BaCO3 and KI gave 1-N-substituted derivatives with quantitative yields, whereas 1-N-alkylation of adenosine was accompanied by significant O-alkylation. Moreover, the reaction of trimethylsilyl derivatives of N-6-acetyl-2 ',3 ',5 '-tri-O-acetyladenosine and N-6-acetyl-3 ',5 '-di-O-acetyl-2 '-deoxyadenosine with alkyl halides leads to the formation of the stable 1-N-substituted adenosines. Dimroth rearrangement of 1-N-substituted adenosines in aqueous ammonia yields pure N-6-substituted adenosines.

  DOI：

  10.1080/15257770.2015.1016169

文献信息

• Synthesis and evaluation of in vitro anticancer activity of some novel isopentenyladenosine derivatives
  作者：Roberta Ottria、Silvana Casati、Ada Manzocchi、Erika Baldoli、Massimo Mariotti、Jeanette A.M. Maier、Pierangela Ciuffreda

  DOI：10.1016/j.bmc.2010.04.093

  日期：2010.6.15

  and elemental analysis. We here show that only two derivatives, 1-(3-methyl-2-butenylamino)-9-(3′-deoxy-β-d-ribofuranosyl)-purine hydrobromide and 2-amino-6-(3-methyl-2- butenylamino)-9-(β-d-ribofuranosyl)-purine, inhibit the growth of T24 cells, although to a lower extent than N6-isopentenyladenosine. We conclude that the integrity of ribosidic and purine moiety and the N6 position of the chain are essential

  本研究描述了N 6-异戊烯基腺苷在T24人膀胱癌细胞上的某些衍生物的合成，表征和评价。特别地，我们已经修饰了核糖部分中的羟基，嘌呤环中异戊烯基链的位置和碱基部分。通过NMR，MS和元素分析的标准研究确认了化合物的结构。我们在这里显示只有两个衍生物，1-（3-甲基-2-丁烯基氨基）-9-（3'-脱氧-β- d-核呋喃糖基）-嘌呤氢溴酸盐和2-氨基-6-（3-甲基-2） -丁烯基氨基）-9-（β- d-核呋喃糖基）-嘌呤抑制T24细胞的生长，尽管程度低于N 6-异戊烯基腺苷。我们得出结论，核糖和嘌呤部分的完整性以及链的N 6位置对于维持抗增殖活性至关重要。
• From synthesis to the biological effect of isoprenoid 2′-deoxyriboside and 2′,3′-dideoxyriboside cytokinin analogues
  作者：Vlasta Matušková、Marek Zatloukal、Tomáš Pospíšil、Jiří Voller、Hana Vylíčilová、Karel Doležal、Miroslav Strnad

  DOI：10.1016/j.phytochem.2022.113481

  日期：2023.1

  Isoprenoid cytokinins are a class of naturally occurring plant signaling molecules. A series of prepared compounds derived from isoprenoid cytokinins (isopentenyladenine, trans-zeatin and cis-zeatin) with attached 2′-deoxy-d-ribose or 2′,3′-dideoxy-d-ribose at the N9 position of the purine were prepared and their biological activities were examined. Different synthetic approaches were employed. The

  类异戊二烯细胞分裂素是一类天然存在的植物信号分子。由类异戊二烯细胞分裂素（异戊烯基腺嘌呤、反式-玉米素和顺式-玉米素）制备的一系列化合物，在嘌呤的N 9位连接有 2'-脱氧-d-核糖或 2',3'-双脱氧-d-核糖制备并检测了它们的生物活性。采用了不同的合成方法。最终化合物通过多种物理化学方法（TLC、HPLC-MS 和 NMR）进行了表征，并通过经典生物测定法（例如苋属植物、烟草愈伤组织、离体小麦叶衰老和拟南芥）测定了它们的细胞分裂素活性根伸长抑制测定。此外，还筛选了用于激活细胞分裂素信号通路（细菌受体、竞争性配体结合和ARR5::GUS测定）的化合物，以提供对 CK 结构-活性关系的详细评估。发现制备的化合物对人体细胞无毒，并且大多数测定显示出游离碱基的最高活性，而 2',3'-双脱氧核糖苷的活性非常弱或没有。与游离碱相比，即使在最高测试浓度（10 -4  moL/l）下，所有 2'-
• Regioselective 1-N-Alkylation and Rearrangement of Adenosine Derivatives
  作者：Vladimir E. Oslovsky、Mikhail S. Drenichev、Sergey N. Mikhailov

  DOI：10.1080/15257770.2015.1016169

  日期：2015.7.3

  Several methods for the preparation of some N-6-substituted adenosines based on selective 1-N-alkylation with subsequent Dimroth rearrangement were developed. The proposed methods seem to be effective for the preparation of natural N-6-isopentenyl- and N-6-benzyladenosines, which are known to possess pronounced biological activities. Direct 1-N-alkylation of 2 ',3 ',5 '-tri-O-acetyladenosine and 3 ',5 '-di-O-acetyl-2 '-deoxyadenosine with alkyl halides in N,N-dimethylformamide (DMF) in the presence of BaCO3 and KI gave 1-N-substituted derivatives with quantitative yields, whereas 1-N-alkylation of adenosine was accompanied by significant O-alkylation. Moreover, the reaction of trimethylsilyl derivatives of N-6-acetyl-2 ',3 ',5 '-tri-O-acetyladenosine and N-6-acetyl-3 ',5 '-di-O-acetyl-2 '-deoxyadenosine with alkyl halides leads to the formation of the stable 1-N-substituted adenosines. Dimroth rearrangement of 1-N-substituted adenosines in aqueous ammonia yields pure N-6-substituted adenosines.