5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine | 68144-26-3

• 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: 5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine
• 英文别名: 5'-azido-N⁶-benzoyl-2',3'-O-isopropylidene-5'-deoxyadenosine；5'-azido-N6-benzoyl-5'-deoxy-2',3'-O-isopropylideneadenosine；5'-azido-N⁶-benzoyl-O^2'_,O3'-isopropylidene-5'-deoxy-adenosine；5'-Azido-N-benzoyl-5'-deoxy-2',3'-O-(1-methylethylidene)-adenosine；N-[9-[(3aR,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-yl]benzamide
• CAS: 68144-26-3
• 化学式: C₂₀H₂₀N₈O₄
• 分子量: 436.43
• InChiKey: KHIBXAXSWIUUTF-QEPJRFBGSA-N

物化性质

• 熔点：
  122-124 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine 在 palladium on activated charcoal 甲醇 、 氨 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 45.0h， 生成 5-氨基-5-脱氧-2,3-O-(1-甲基亚乙基)-腺苷酸
  参考文献：
  名称：

  Synthesis of an Uncharged cAMP-Analogue

  摘要：

  3'-O,5'-N-(N-phenylsulfonyliminocarbonyl)-5'-amino-5'-deoxy adenosine, an uncharged cAMP-analogue was synthesized. This was accomplished by treatment of 5'amino-5'-deoxy-2',3'-O-isopropylidene adenosine with dimethyl N-phenylsulfonyldithiocarbamate. After removal of the isopropylidene protecting group and treatment of the intermediate with benzoyl chloride, cyclisation was carried out in DMF containing 10 equivalents of potassium tert-butoxide. Final deprotection of the adenine moiety was carried out with hydrazine hydrate.

  DOI：

  10.1080/15257779508014657
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 吡啶 、 sodium azide 、 乙醇 、 氨 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 生成 5'-azido-5'-deoxy-N⁶-benzoyl-2',3'-O-isopropylidene adenosine
  参考文献：
  名称：

  Synthesis of an Uncharged cAMP-Analogue

  摘要：

  3'-O,5'-N-(N-phenylsulfonyliminocarbonyl)-5'-amino-5'-deoxy adenosine, an uncharged cAMP-analogue was synthesized. This was accomplished by treatment of 5'amino-5'-deoxy-2',3'-O-isopropylidene adenosine with dimethyl N-phenylsulfonyldithiocarbamate. After removal of the isopropylidene protecting group and treatment of the intermediate with benzoyl chloride, cyclisation was carried out in DMF containing 10 equivalents of potassium tert-butoxide. Final deprotection of the adenine moiety was carried out with hydrazine hydrate.

  DOI：

  10.1080/15257779508014657

文献信息

• Molecular recognition of tyrosinyl adenylate analogues by prokaryotic tyrosyl tRNA synthetases
  作者：Pamela Brown、Christine M. Richardson、Lucy M. Mensah、Peter J. O'Hanlon、Neal F. Osborne、Andrew J. Pope、Graham Walker

  DOI：10.1016/s0968-0896(99)00192-3

  日期：1999.11

  modelling and synthetic studies have been carried out on tyrosinyl adenylate and analogues to probe the interactions seen in the active site of the X-ray crystal structure of tyrosyl tRNA synthetase from Bacillus stearothermophilus, and to search for new inhibitors of this enzyme. Micromolar and sub-micromolar inhibitors of tyrosyl tRNA synthetases from both B. stearothermophilus and Staphylococcus aureus have

  已经对酪氨酰腺苷酸及其类似物进行了分子建模和合成研究，以探测在嗜热脂肪芽孢杆菌的酪氨酰tRNA合成酶的X射线晶体结构的活性位点中观察到的相互作用，并寻找该酶的新抑制剂。已经合成了来自嗜热脂肪芽孢杆菌和金黄色葡萄球菌的酪氨酰tRNA合成酶的微摩尔和亚微摩尔抑制剂。腺嘌呤环对酪氨酸腺苷酸与酶结合的重要性以及水介导的氢键相互作用的重要性已得到强调。通过与金黄色葡萄球菌酶的同源性建模以及配体对接研究进一步支持了抑制数据。
• [EN] CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS DI-NUCLÉOTIDES CYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：IMMUNE SENSOR LLC

  公开号：WO2017161349A1

  公开（公告）日：2017-09-21

  Disclosed are cyclic-di-nucleotide cGAMP analogs, methods of synthesizing the compounds, pharmaceutical compositions comprising the compounds thereof, and use of compounds and compositions in medical therapy.

  揭示了环二核苷酸cGAMP类似物，合成这些化合物的方法，包括这些化合物的药物组合物，以及在医学治疗中使用这些化合物和组合物的用途。
• A Tractable and Efficient One-Pot Synthesis of 5'-Azido-5'-deoxyribonucleosides
  作者：Theodore Peterson、Tobin Streamland、Ahmed Awad

  DOI：10.3390/molecules19022434

  日期：——

  Synthetic routes to 5'-azidoribonucleosides are reported for adenosine, cytidine, guanosine, and uridine, resulting in a widely applicable one-pot methodology for the synthesis of these and related compounds. The target compounds are appropriate as precursors in a variety of purposive syntheses, as the synthetic and therapeutic relevance of azido- and amino-modified nucleosides is expansive. Furthermore

  报道了腺苷、胞苷、鸟苷和尿苷的 5'-叠氮核糖核苷的合成路线，从而为合成这些和相关化合物提供了一种广泛适用的一锅法。目标化合物适合作为各种有目的的合成中的前体，因为叠氮基和氨基修饰的核苷的合成和治疗相关性是广泛的。此外，在将醇转化为叠氮化物的过程中，这些方法为 Mitsunobu 和其他更困难的反应提供了一种易于处理的替代方法。
• Oligonucleotide Analogues with Integrated Bases and Backbones. Part 24
  作者：Katja Chiesa、Alyena Shvoryna、Bruno Bernet、Andrea Vasella

  DOI：10.1002/hlca.201000011

  日期：2010.4

  Inspection of Maruzen models and force‐field calculations suggest that oligonucleotide analogues integrating backbone and bases (ONIBs) with an aminomethylene linker form similar cyclic duplexes as the analogous oxymethylene linked dinucleosides. The self‐complementary adenosine‐ and uridine‐derived aminomethylene‐linked A*[n]U dinucleosides 15–17 were prepared by an aza‐Wittig reaction of the aldehyde

  对Maruzen模型和力场计算的检查表明，整合有骨架和碱基（ONIB）与氨基亚甲基接头的寡核苷酸类似物与甲醛与二甲基核苷类似，形成了类似的环状双链体。自身互补腺苷和尿苷衍生的氨基亚甲基联A * [ Ñ ] V二核苷15 - 17通过氮杂制备维蒂希的醛的反应10与叠氮化物衍生的亚氨基正膦6。序列异构U * [ Ñ ]甲二核苷18 - 20类似地从醛制备3和叠氮化12。的Ñ -乙胺5，乙酰胺7和14，和胺13，制备作为用于二核苷的构象分析的引用。与计算结果相反，N-乙胺5以分子内H键合的羟基亚氨基互变异构体形式存在。通过1 H-NMR和CD光谱研究了这些二核苷在CDCl 3中的缔合。A * [ n ] U二核苷16和17的缔合作用比序列异构体19和20的缔合作用更强; 16个环状双链体优先形成Watson – Crick型碱基对，而17、19和20则同时显示Watson – Crick型和Ho
• Design, synthesis, and molecular modeling studies of 5′-deoxy-5′-ureidoadenosine: 5′-ureido group as multiple hydrogen bonding donor in the active site of S-adenosylhomocysteine hydrolase
  作者：Ting Wang、Hyun Joo Lee、Dilip K. Tosh、Hea Ok Kim、Shantanu Pal、Sun Choi、Yoonji Lee、Hyung Ryong Moon、Long Xuan Zhao、Kang Man Lee、Lak Shin Jeong

  DOI：10.1016/j.bmcl.2007.06.013

  日期：2007.8

  5'-Deoxy-5'-ureidoadenosine was designed and synthesized as a potent inhibitor of S-adenosylhomocysteine hydrolase (SAH), in which 5'-ureido group acted as multiple hydrogen bonding donor in binding with active site residues of SAH in the molecular modeling study. (c) 2007 Published by Elsevier Ltd.