1-(2'-脱氧核糖基)-2-嘧啶酮 | 22003-30-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 1-(2'-脱氧核糖基)-2-嘧啶酮
• 英文名称: 1-β-D-deoxyribofuranosyl-1,2-dihydropyrimidin-2-one
• 英文别名: 1-(2'-Desoxy-β-D-ribofuranosyl)-2-(1H)-pyrimidinon；1-(2'-Desoxy-β-D-ribofuranosyl)-2(1H)-pyrimidinon；1-(β-D-2'-Deoxyribosyl)-2-pyrimidinone；2'-deoxyzebularine；β-dZeb；dZ；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 22003-30-1
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: QEJOIGZDWKFVCO-XLPZGREQSA-N

物化性质

• 沸点：
  450.2±55.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2'-脱氧核糖基)-2-嘧啶酮 在 1H-1,2,4-三唑 、 N-甲基咪唑 、 4-nitrobenzaldehyde oxime 、 三乙胺 、 四甲基胍 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 23.33h， 生成 5'-O-Monomethoxytritylthymidyl-(3'-5')-thymidyl-(3'-5')-1-(2'-desoxy-β-D-ribofuranosyl)-2(1H)-pyrimidinon
  参考文献：
  名称：

  核苷和核苷酸。Teil 20.合成二酯和三酯方法的脱氧核糖核酸寡核苷酸核苷酸2（1 H）-嘧啶碱基† ‡

  摘要：

  核苷和核苷酸。第20部分，以2（1 H）-嘧啶酮为基础的二酯和三酯方法合成脱氧核糖寡核苷酸

  DOI：

  10.1002/hlca.19830660131
• 作为产物：
  描述：

  Phosphoric acid mono-[(2R,3S,5R)-3-hydroxy-5-(2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester; compound with ammonia 在 poison of Crotalus adamanteus 、 alkaline phosphatase 作用下， 生成 1-(2'-脱氧核糖基)-2-嘧啶酮
  参考文献：
  名称：

  核苷和核苷酸。TEIL 15.合成冯Desoxyribonucleosid-monophosphaten UND -triphosphaten MIT 2（1 ħ）-Pyrimidinon，2（1 ħ）-Pyridinon UND 4-氨基- 2（1 ħ）-pyridinon ALS倍欣†往最‡

  摘要：

  核苷和核苷酸。脱氧核苷单磷酸和核苷三磷酸部分15合成2（1 ħ） -嘧啶酮，2（1 ħ） -吡啶酮和4-氨基-2（1个H ^） -吡啶酮作为基地

  DOI：

  10.1002/hlca.19800630842

文献信息

• Nucleoside und Nucleotide. Teil 22. Synthese eines Tridecanucleosiddodecaphosphats, das die unnatürliche Base 2(1<i>H</i>)-Pyrimidinon enthält
  作者：Rolf Altermatt、Christoph Tamm

  DOI：10.1002/hlca.19850680221

  日期：1985.3.27

  Nucleosides and Nucleotides. Part 22. Synthesis of a Tridecanucleoside Dodecaphosphate Containing the Unnatural Base 2(1H)-Pyrimidinone

  核苷和核苷酸。第22部分。包含非天然碱2（1 H）-嘧啶酮的十三碳十二烷基核苷十二磷酸的合成
• Polynucleotide assay reagent and method
  申请人：ANTIVIRALS INC.

  公开号：EP0639582A2

  公开（公告）日：1995-02-22

  The invention provides a use of a morpholino subunit of the formula (I) where P is a purine or pyrimidine base-pairing moiety, and T is H or an N-protective group, for the production of a polymer capable of hydrogen-bonding to complementary bases in a polynucleotide, where in said polymer (i) the subunits are joined predominantly by substantially uncharged, achiral linkages, and (ii) each linkage joins the morpholino nitrogen of one subunit to the 5' exocyclic carbon of an adjacent subunit.

  本发明提供了式 (I) 吗啉亚基的用途 其中 P 是嘌呤或嘧啶碱基配对分子，T 是 H 或 N 保护基团，用于生产能够与多核苷酸中的互补碱基发生氢键连接的聚合物，在所述聚合物中，(i) 亚基主要通过基本上不带电的非手性连接物连接，(ii) 每个连接物将一个亚基的吗啉基氮连接到相邻亚基的 5'外环碳上。
• Activation of <i>p16</i> Gene Silenced by DNA Methylation in Cancer Cells by Phosphoramidate Derivatives of 2′-Deoxyzebularine
  作者：Christine B. Yoo、Rocco Valente、Costantino Congiatu、Federica Gavazza、Annette Angel、Maqbool A. Siddiqui、Peter A. Jones、Christopher McGuigan、Victor E. Marquez

  DOI：10.1021/jm8005965

  日期：2008.12.11

  We report herein the application of the phosphoramidate ProTide technology to improve the metabolism of the DNA methytransferase inhibitor, zebularine (Z). Zebularine is a riboside that must undergo a complex metabolic transformation before reaching the critical 2'-deoxyzebularine 5'-triphosphate (dZTP). Because 2'-deoxyzebularine (dZ) is not phosphorylated and therefore inactive, the ProTide strategy was employed to bypass the lack of phosphorylation of dZ and the inefficient reduction of zebularine 5'-diphosphate by ribonucleotide-diphosphate reductase required for zebularine. Several compounds were identified as more potent inhibitors of DNA methylation and stronger inducers of p16 tumor suppressor gene than zebularine. However, their activity was dependent on the administration of thymidine to overcome the potent inhibition of thymidylate synthase (TS) and deoxycytidine monophosphate (dCMP) deaminase by dZMP, which deprives cells of essential levels of thymidine. Intriguingly, the activity of the ProTides was cell line-dependent, and activation of p16 was manifest only in Cf-Pac-1 pancreatic ductal adenocarcinoma. cells.
• Efficient synthesis of 2′-deoxyzebularine and its α-anomer by the silyl method of N-glycosylation. Crystal structures and conformational study in solution
  作者：Katarzyna Ebenryter-Olbinska、Janina Karolak-Wojciechowska、Elzbieta Sochacka

  DOI：10.1016/j.carres.2014.03.018

  日期：2014.6

  2'-Deoxyzebularine and its alpha-anomer have been efficiently synthesized with relatively high stereoselectivity by a modified procedure of the silyl method of the N-glycosidic bond formation. An SnCl4-catalyzed condensation of silylated pyrimidin-2-one with 1-alpha-chloro-3,5-di-O-p-toluoy1-2-deoxy-D-ribofuranose under kinetic control condition (-33 degrees C, 1,2-dichloroethane) led to the mixture of beta- and alpha-anomeric nucleosides in 3:1 ratio. Analogous condensation at +35 degrees C (thermodynamic control conditions) provided mainly p-toluoyl protected alpha-2'-deoxyzebularine (alpha:beta= 4:1), easily separated by crystallization from the anomeric mixture. The structures of both 2'-deoxyzebularine anomers were confirmed by X-ray analysis of the crystals and conformational studies in solution performed using an NMR method. (C) 2014 Elsevier Ltd. All rights reserved.
• Mild acid hydrolysis of 2-pyrimidinone-containing DNA fragments generates apurinic/apyrimidinic sites
  作者：Joseph A Iocono、Brian Gildea、Larry W McLaughlin

  DOI：10.1016/s0040-4039(00)94363-6

  日期：1990.1