N-(2-methyl-1-oxopropyl)-2',3'-dibenzoylguanosine | 66466-51-1

• 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-(2-methyl-1-oxopropyl)-2',3'-dibenzoylguanosine
• 英文别名: [(2R,3R,4R,5R)-4-benzoyloxy-2-(hydroxymethyl)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] benzoate
• CAS: 66466-51-1
• 化学式: C₂₈H₂₇N₅O₈
• 分子量: 561.551
• InChiKey: XWVZATALEMCBIK-GUQHISFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(2-methyl-1-oxopropyl)-2',3'-dibenzoylguanosine 在 Dowex-50 、 氨 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 122.0h， 生成 CpG
  参考文献：
  名称：

  Studies on transfer ribonucleic acids and related compounds. XXXIV. Stepwise diester or partial triester synthesis of penta- to octanucleotides corresponding to residues 41-46, 47-54, 61-65 and 66-71 of tRNAfMet of E. coli.

  摘要：

  通过逐步添加单核苷酸，合成了对应于tRNAMetf第41-46位和第47-54位的六核苷酸和八核苷酸。这个八核苷酸是通过这种方法合成的最大的寡核糖核酸。通过部分三酯化中间体，合成了一个五核苷酸（第61-65位）和一个六核苷酸（第66-71位）。去阻断产物通过离子交换色谱法进行纯化，并利用酶解法进行表征。这些寡核苷酸被用作RNA连接酶连接反应中的底物。

  DOI：

  10.1248/cpb.28.2450
• 作为产物：
  描述：

  N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(trityloxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 N-(2-methyl-1-oxopropyl)-2',3'-dibenzoylguanosine
  参考文献：
  名称：

  Design and Synthesis of α-Carboxy Phosphononucleosides

  摘要：

  Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.

  DOI：

  10.1021/jo101738e

文献信息

• 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。
• Synthesis of certain nucleoside methylenediphosphonate sugars as potential inhibitors of glycosyltransferases
  作者：Morteza M. Vaghefi、Ralph J. Bernacki、William J. Hennen、Roland K. Robins

  DOI：10.1021/jm00391a021

  日期：1987.8

  The synthesis of alpha-D-glucopyranosyl 1-(methylenediphosphonate) (11), alpha-D-galactopyranosyl 1-(methylenediphosphonate) (14), and alpha-D-mannopyranosyl 1-(methylenediphosphonate) (17) has been accomplished. [(Di-phenoxyphosphinyl)methyl]phosphonic acid (diphenyl-MDP) (5), synthesized by two different procedures, was fused with beta-D-glucopyranose pentaacetate followed by catalytic hydrogenation to give 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl methylenediphosphonate (glucose-MDP) (10). The anomeric configuration of 10 was assigned on the basis of NMR spectral studies. Condensation of 10 with 2',3'-di-O-acetyladenosine was accomplished by using 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) as coupling agent, and removal of the blocking groups gave adenosine 5'-[(alpha-D-glucopyranosylhydroxyphosphinyl)methyl]phosphonate (20). Uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl] phosphonate (23) and guanosine 5'-[(alpha-D-mannopyranosylhydroxyphosphinyl)methyl]phosphonate (26) were similarly prepared. Using a specific glycoprotein galactosyltransferase (EC 2.4.1.38) assay, uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl]phosphonate (23) demonstrated competitive inhibition with an apparent Ki of 97 microM. The adenosine analogue did not inhibit the enzyme. None of the above compounds show any in vitro antitumor or antiviral activity. Such specific inhibitors of glycosyltransferases may serve as specific probes to study various glycosyltransferases that might be involved in the process of metastasis.
• Markiewicz, Wojciech T.; Niewczyk, Anna; Gdaniec, Zofia, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 411 - 424
  作者：Markiewicz, Wojciech T.、Niewczyk, Anna、Gdaniec, Zofia、Adamiak, Dorota A.、Dauter, Zbigniew、Rypniewski, Wojciech、Chmielewski, Marcin

  DOI：——

  日期：——
• VAGHEFI, M. M.;BERNACKI, R. J.;HENNEN, W. J.;ROBINS, R. K., J. MED. CHEM., 30,(1987) N 8, 1391-1399
  作者：VAGHEFI, M. M.、BERNACKI, R. J.、HENNEN, W. J.、ROBINS, R. K.

  DOI：——

  日期：——
• Design and Synthesis of α-Carboxy Phosphononucleosides
  作者：Sebastien Debarge、Jan Balzarini、Anita R. Maguire

  DOI：10.1021/jo101738e

  日期：2011.1.7

  Rhodium catalyzed O-H insertion reactions employing alpha-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an alpha-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2.