N-benzoyl-2',3'-di-O-benzoyladenosine | 14985-43-4

• 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: N-benzoyl-2',3'-di-O-benzoyladenosine
• 英文别名: N⁶,O^2',O^3'-tribenzoyladenosine；2',3'-Di-O-benzoyl-N6-benzoyl-L-adenosine；[(2R,3R,4R,5R)-5-(6-benzamidopurin-9-yl)-4-benzoyloxy-2-(hydroxymethyl)oxolan-3-yl] benzoate
• CAS: 14985-43-4
• 化学式: C₃₁H₂₅N₅O₇
• 分子量: 579.569
• InChiKey: PDOVRTQXHVPGAF-UQCYUJMQSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-benzoyl-2',3'-di-O-benzoyladenosine 在 palladium on activated charcoal 吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 反应 66.0h， 生成 N⁶-benzoyl-9-[2',3'-di-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-β-D-ribohexofuranosyl]adenine
  参考文献：
  名称：

  Design, Synthesis, and Antiviral Activity of Adenosine 5‘-Phosphonate Analogues as Chain Terminators against Hepatitis C Virus

  摘要：

  A series of adenosine 5'-phosphonate analogues were designed to mimic naturally occurring adenosine monophosphate. These compounds (1-5) were synthesized and evaluated in a cellular hepatitis C virus (HCV) replication assay. To improve cellular permeability and enhance the anti-HCV activity of these phosphonates, a bis(S-acyl-2-thioethyl) prodrug for compound 5 was prepared, and its cellular activity was determined. To elucidate the mechanism of action of these novel adenosine phosphonates, their diphosphate derivatives (1a-5a) were synthesized. Further nucleotide incorporation assays by HCV NS5B RNA-dependent RNA polymerase revealed that 2a and 3a can serve as chain terminators, whereas compounds 1a, 4a, and 5a are competitive inhibitors with ATP. Additional steady-state kinetic analysis determined the incorporation efficiency of 2a and 3a as well as the inhibition constants for 1a, 4a, and 5a. The structure -activity relationships among these compounds were analyzed, and the implication for nucleoside phosphonate drug design was discussed.

  DOI：

  10.1021/jm049029u
• 作为产物：
  描述：

  N6-苯甲酰基腺苷 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 N-benzoyl-2',3'-di-O-benzoyladenosine
  参考文献：
  名称：

  Synthesis and structural characterization of diastereomeric isomers of RNA trimer adenylyl(3′-5′)adenylyl(3′-5′)adenosine

  摘要：

  We have synthesized the diastereomeric isomers of adenylyl(3'-5')adenylyl(3'-5')adenosine (ApApA), and investigated their helical structures and hybridization properties with D-poly(U) by circular dichroism (CD) and UV melting experiments. The configuration of the 5'-end residue of ApApA has little effect on the helical structure. The configuration of the 3'-end residue has little effect on the stability of the triplex, and the chiral modifications cause complicated effects on the helical structure of ApApA and its triplex-forming ability with D-poly(U), depending on the site of the modification. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.026

文献信息

• Synthesis and Properties of Aminoacylamido-AMP:  Chemical Optimization for the Construction of an <i>N</i>-Acyl Phosphoramidate Linkage
  作者：Tomohisa Moriguchi、Terukazu Yanagi、Masao Kunimori、Takeshi Wada、Mitsuo Sekine

  DOI：10.1021/jo0008338

  日期：2000.12.1

  This paper describes the design and synthesis of a new type of aminoacyl-adenylate analogue (aa-AMPN) having an N-acyl phosphoramidate linkage where the oxygen atom of the mixed anhydride bond of aminoacyl-adenylate (aa-AMP) is replaced by an amino group. This new type of aa-AMP analogue is expected to be useful as material for studies on the recognition mechanism of the aminoacylation of tRNA and

  本文介绍了具有N-酰基氨基磷酸酯键的新型氨基酰基-腺苷酸类似物（aa-AMPN）的设计和合成，其中氨基酰基-腺苷酸（aa-AMP）的混合酸酐键的氧原子被氨基。这种新型的aa-AMP类似物有望用作研究tRNA氨基酰化和其他生化反应识别机制的材料。羧酰胺的亚磷酰胺衍生物与核苷衍生物的缩合失败，因为活化的亚磷酰胺衍生物不仅与羟基反应，而且与另一种反应性物质反应。通过5'-O-亚磷酰胺基腺苷衍生物与羧酰胺衍生物的反应研究了另一种方法。选择TBTr和TSE基团分别用于保护氨基酸酰胺的氨基和磷酸基。详细研究表明，使用5-（3,5-二硝基苯基）-1H-四唑作为亚磷酰胺的活化催化剂可在10分钟内迅速缩合，从而得到完全保护的aa-AMPN衍生物。没有发生副反应。通过两步程序对这些产物进行脱保护，得到高产率的aa-AMPN衍生物。还证明由此获得的aa-AMPN在酸性和碱性条件下均是稳定的，例如0.1M HCl（pH
• A Mild and Efficient Detritylation of Some Carbohydrate Derivatives
  作者：J. Fuentes、T. Cuevas、M. A. Pradera

  DOI：10.1080/00397919408019048

  日期：1994.8

  Abstract Solutions of Cl2 in CHCl3 are used to remove the trityl radical from CH2OTr groups of carbohydrate derivatives. This method does not produce cleavage of the C-N bond in nucleosides. An N-dialkoxy-carbonylvinyl group can be simultaneously removed.

  摘要 Cl2 在CHCl3 中的溶液用于从碳水化合物衍生物的CH2OTr 基团中去除三苯甲基自由基。这种方法不会导致核苷中 CN 键的断裂。可以同时除去N-二烷氧基-羰基乙烯基。
• Methoxyethoxymethyl group for the protection of uracil residue in oligoribonucleotide synthesis
  作者：Hiroshi Takaku、Souichi Ueda、Tsunehiko Ito

  DOI：10.1016/s0040-4039(00)87869-7

  日期：——

  Methoxyethoxymethyl group (MEM) was useful protecting group for the protection of uracil residue. This group was selectively introduced into uracil residue in good yield and removed under mild conditions.

  甲氧基乙氧基甲基（MEM）是用于保护尿嘧啶残基的有用保护基。将这一组以高收率选择性地引入尿嘧啶残基中，并在温和条件下除去。
• Synthesis of 2'- or 3'-o-(4-methoxybenzyl)nucleosides and its application in the 3'-terminal nonanucleotide sequence of rous sarcoma virus 35S RNA synthesis
  作者：Kazuo Kamaike、Hiromichi Tsuchiya、Kazuaki Imai、Hiroshi Takaku

  DOI：10.1016/s0040-4020(01)82051-2

  日期：1986.1

  2'- or 3'-O-(4-Methoxybenzyl)nucleoside derivatives were synthesized by treatment of uridine, N4-benzoylcytidine, N6-benzoyladenosine, and N2-benzoylguanosine with 4-methoxy-phenyldiazomethane. The separation of 2'- or 3'-isomers became possible on a silica gel column chromatography by using N-acylated nucleosides and these compounds could be used as useful starting materials for the synthesis of

  通过用4-甲氧基-苯基重氮甲烷处理尿苷，N 4-苯甲酰基胞苷，N 6-苯甲酰基腺苷和N 2-苯甲酰基鸟苷来合成2'-或3'-O-（4-甲氧基苄基）核苷衍生物。通过使用N-酰化的核苷，可以在硅胶柱色谱上分离2'-或3'-异构体，并且这些化合物可用作通过磷酸三酯法合成寡核糖核苷酸的有用起始原料。通过快速方法合成了三聚体嵌段UU-Cp，AC-Cp和ACA。劳斯肉瘤病毒35S RNA的3'端九核苷酸UUCACCACA是通过三聚体的嵌段缩合获得的。
• Stereochemistry of Internucleotide Bond Formation by the H-Phosphonate Method. 1. Synthesis and ³¹P Nmr Analysis of 16 Diribonulceoside (3′-5′)-H-Phosphonates and the Corresponding Phosphorothioates
  作者：Michal Sobkowski、Jadwiga Jankowska、Adam Kraszewski、Jacek Stawinski

  DOI：10.1080/15257770500265729

  日期：2005.9.1

  Sixteen diribonucleoside (3′-5′)-H-phosphonates were synthesized via condensation of the protected ribonucleoside 3′-H-phosphonates with nucleosides, and the influence of a nucleoside sequence on the observed stereoselectivity was analyzed. 31P NMR spectroscopy was used to evaluate a relationship between chemical shift and absolute configuration at the phosphorous center of the H-phosphonate diesters

  通过受保护的核糖核苷 3'-H-膦酸酯与核苷的缩合合成了 16 种二核糖核苷 (3'-5')-H-膦酸酯，并分析了核苷序列对观察到的立体选择性的影响。31P NMR光谱用于评估H-膦酸二酯以及相应硫代磷酸二酯的磷中心的化学位移和绝对构型之间的关系。尽管在大多数情况下发现了这种相关性，但也有一些例外，即由 RP 和 SP 非对映异构体产生的共振的相对位置颠倒的规则。