2'-deoxy-2'-α-methyl-N4-benzoylcytidine | 733050-27-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2'-deoxy-2'-α-methyl-N4-benzoylcytidine
• 英文别名: 2'-deoxy-2'-α-methyl-N⁴-benzoylcytidine
• CAS: 733050-27-6
• 化学式: C₁₇H₁₉N₃O₅
• 分子量: 345.355
• InChiKey: HDHVSPCOPCQJAU-UUFMSHNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113.68
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-α-methyl-N4-benzoylcytidine 在 吡啶 、 N-甲基咪唑 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-[1-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-methyloxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
  参考文献：
  名称：

  Synthesis of the Phosphoramidite Derivatives of 2‘-Deoxy-2‘-C-α-methylcytidine and 2‘-Deoxy-2‘-C-α-hydroxymethylcytidine:  Analogues for Chemical Dissection of RNA's 2‘-Hydroxyl Group

  摘要：

  Oligonucleotides containing 2'-C-alpha-methyl and 2'-C-alpha-hydroxymethyl modifications enable strategies for delineation of the distinctive role fulfilled by the 2'-hydroxyl group in RNA structure and function. Synthetic routes to the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine (14%, 15 steps) and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine (19%, 10 steps) from methyl 3,5-di-O-(4-chlorobenzyl)-alpha-D-ribofuranoside are developed.

  DOI：

  10.1021/jo0495337
• 作为产物：
  描述：

  methyl 3,5-di-O-(4-chlorobenzyl)-2-keto-α-D-ribofuranoside 在 palladium dihydroxide 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 硫酸氢铵 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 2,4,6-三异丙基苯磺酰氯 、 偶氮二异丁腈 、 triethylamine trihydrofluoride 、 氢气 、 仲丁基锂 、 三正丁基氢锡 、 三乙胺 、 六甲基二硅氮烷 、 硫代氯甲酸苯酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 环己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 85.0h， 生成 2'-deoxy-2'-α-methyl-N4-benzoylcytidine
  参考文献：
  名称：

  Synthesis of the Phosphoramidite Derivatives of 2‘-Deoxy-2‘-C-α-methylcytidine and 2‘-Deoxy-2‘-C-α-hydroxymethylcytidine:  Analogues for Chemical Dissection of RNA's 2‘-Hydroxyl Group

  摘要：

  Oligonucleotides containing 2'-C-alpha-methyl and 2'-C-alpha-hydroxymethyl modifications enable strategies for delineation of the distinctive role fulfilled by the 2'-hydroxyl group in RNA structure and function. Synthetic routes to the phosphoramidite derivatives of 2'-deoxy-2'-C-alpha-methylcytidine (14%, 15 steps) and 2'-deoxy-2'-C-alpha-hydroxymethylcytidine (19%, 10 steps) from methyl 3,5-di-O-(4-chlorobenzyl)-alpha-D-ribofuranoside are developed.

  DOI：

  10.1021/jo0495337

文献信息

• Influence of conformationally restricted pyrimidines on the activity of 10–23 DNAzymes
  作者：Laura Robaldo、Franco Izzo、María Dellafiore、Cecilia Proietti、Patricia V. Elizalde、Javier M. Montserrat、Adolfo M. Iribarren

  DOI：10.1016/j.bmc.2012.02.047

  日期：2012.4

  The catalytic core of a 10-23 DNAzyme was modified introducing conformationally restricted nucleosides such as (2'R)-, (2'S)-2'-deoxy-2'-C-methyluridine, (2'R)-, (2'S)-2'-deoxy-2'-C-methylcytidine, 2,2'-anhydrouridine and LNA-C, in one, two or three positions. Catalytic activities under pseudo first order conditions were compared at different Mg2+ concentrations using a short RNA substrate. At low Mg2+ concentrations, triple modified DNAzymes with similar kinetic performance to that displayed by the non-modified control were identified. In the search for a partial explanation of the obtained results, in silico studies were carried out in order to explore the conformational behavior of 2'-deoxy-2'-C-methyl-pyrimidines in the context of a loop structure, suggesting that at least partial flexibility is needed for the maintenance of activity. Finally, the modified 2'-C-methyl DNAzyme activity was tested assessing the inhibition of Stat3 expression and the decrease in cell proliferation using the human breast cancer cell line T47D. (C) 2012 Elsevier Ltd. All rights reserved.