1'-Pivaloyl-2'-deoxyuridine | 173349-24-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1'-Pivaloyl-2'-deoxyuridine
• 英文别名: 1-[(2S,4S,5R)-2-(2,2-dimethylpropanoyl)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 173349-24-1
• 化学式: C₁₄H₂₀N₂O₆
• 分子量: 312.323
• InChiKey: DUEFCDHCFYWDRQ-QIBSRJKCSA-N

物化性质

• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1'-Pivaloyl-2'-deoxyuridine 在 air 、 水 作用下， 反应 6.0h， 生成 D-(+)-核糖酸-gamma-内酯
  参考文献：
  名称：

  Fate of the C-1′ peroxyl radical in the 2′-deoxyuridine system

  摘要：

  光生2-脱氧尿苷-1-基自由基与水中的分子氧反应形成2-脱氧核糖酸内酯的机理已经过研究。

  DOI：

  10.1039/a802375a
• 作为产物：
  描述：

  1-(3'-deoxy-β-D-psicofuranosyl)uracil 在 吡啶 、 氟化铵 作用下， 以 甲醇 为溶剂， 生成 1'-Pivaloyl-2'-deoxyuridine
  参考文献：
  名称：

  Independent Generation and Reactivity of 2‘-Deoxyurid-1‘-yl

  摘要：

  DOI：

  10.1021/jo951769a

文献信息

• Spectra and structure of the 2′-deoxyuridin-1′-yl radical
  作者：Chryssostomos Chatgilialoglu、Thanasis Gimisis、Maurizio Guerra、Carla Ferreri、Calvin J. Emanuel、John H. Horner、Martin Newcomb、Macro Lucarini、Gian Franco Pedulli

  DOI：10.1016/s0040-4039(98)00731-x

  日期：1998.6

  The title C-1′ radical, obtained by photolysis of the corresponding tert-butyl ketone in water, was studied spectroscopically by EPR and laser flash photolysis methods and computationally.

  通过相应的叔丁基酮在水中的光解，通过EPR和激光闪光光解方法对光谱进行了研究，并通过计算研究了标题C-1'自由基。
• Synthesis and Biological Evaluation of Novel 1′‐Branched and Spironucleoside Analogues
  作者：Chryssostomos Chatgilialoglu、Carla Ferreri、Thanasis Gimisis †、Marinella Roberti、Jan Balzarini、Erik De Clercq

  DOI：10.1081/ncn-200031391

  日期：2004.1.1

  Novel anomeric spironucleosides and 1′‐cyano‐2′,3′‐didehydro‐2′,3′‐dideoxyuridine, a structural analogue of known anti‐HIV agents, were prepared by nucleophilic addition of organolithium reagents to 1′‐cyano‐2′‐deoxy‐ and 1′‐cyano‐2′‐deoxy‐2′β‐bromo‐uridine derivatives, respectively. The yield and distribution of products depended on the reaction conditions, which were studied in detail. Although none

  通过将有机锂试剂亲核加成到 1'-氰基-2 上制备了新型异头螺核苷和 1'-氰基-2',3'-didehydro-2',3'-dideoxyuridine，一种已知抗 HIV 药物的结构类似物'-deoxy- 和 1'-cyano-2'-deoxy-2'β-bromo-uridine 衍生物，分别。产物的产率和分布取决于反应条件，对此进行了详细研究。尽管这些化合物都没有表现出抗病毒活性，但有两种化合物对鼠白血病和人 T 淋巴细胞都表现出细胞抑制活性。†也是通讯作者。
• Direct Evidence for Bimodal DNA Damage Induced by Tirapazamine
  作者：J. Scott Daniels、Kent S. Gates、Christopher Tronche、Marc M. Greenberg

  DOI：10.1021/tx980184j

  日期：1998.11.1

  The ability of tirapazamine (1, 3-amino-1,2,4-benzotriazine 1,4-dioxide, SR4233) to fix DNA radical lesions is demonstrated by studying the reaction between the antitumor drug and an oligonucleotide radical that is independently produced at a defined site within a biopolymer. Using beta-mercaptoethanol as a competitor, it was determined that tirapazamine traps a C1'-nucleotide radical with a rate constant of similar to 2 x 10(8) M-1 s(-1) Product and isotopic labeling studies suggest that tirapazamine reacts with the radical via covalent adduct formation, resulting primarily from reaction at the N-oxide oxygen. Intermediate covalent adducts could not be observed, but are postulated to decompose to the alkaline labile 2'-deoxyribonolactone lesion. These experiments affirm recent proposals suggesting that tirapazamine can serve as a surrogate for O-2 in converting DNA radicals into toxic strand damage events.
• Anionically induced formation of anomeric spironucleosides from 1′-C-cyano-2′-deoxyuridine
  作者：Chryssostomos Chatgilialoglu、Carla Ferreri、Thanasis Gimisis

  DOI：10.1016/s0040-4039(99)00273-7

  日期：1999.4

  The reaction of the 1'-C-cyano-2'-deoxyuridine derivative 1 with organolithium reagents can be favorably tuned to give a new class of anomeric spironucleosides. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Kinetics and Stereoselectivity of Thiol Trapping of Deoxyuridin-1‘-yl in Biopolymers and Their Relationship to the Formation of Premutagenic α-Deoxynucleotides
  作者：Jae-Taeg Hwang、Marc M. Greenberg

  DOI：10.1021/ja990152y

  日期：1999.5.1

  alpha-Deoxynucleotides are potentially deleterious lesions when produced in DNA. They are presumably formed in part via misrepair of the respective C1'-nucleotide radicals by thiols. However, the selectivity and extent to which these lesions are formed via this pathway has not been ascertained. Using the ability to independently generate deoxyuridin-1'-yl (4) at a defined site in a biopolymer, we have determined that thiol trapping in duplex DNA occurs with high stereoselectivity from the ct-face, resulting in restoration of the naturally occurring beta-deoxynucleotide. The observed stereoselectivity of thiol trapping in duplex DNA suggests that 4 is intrahelical. The rate constant for hydrogen atom donation to 4 is reduced 2-3-fold in double-stranded DNA compared to single-stranded DNA. This decrease is attributed to the relative inaccessibility of the C1'-position in duplex DNA. The combination of these two properties of 4 indicates that, at O-2 concentrations present in aerated water, alpha-deoxynucleotide formation should constitute a minor component of the reactivity of C1'-radicals. Accordingly, the chemical biology of other lesions derived from formal damage at C1'-position could be significant.