1-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone | 109025-52-7

• 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-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone
• 英文别名: 1-(3',5'-Di-O-acetyl-2'-desoxy-β-D-ribofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)pyrimidinon；4-(1,2,4-triazol-1-yl)-1-(β-D-3,5-di-O-acetylribofuranosyl)pyrimidin-2(1H)-one；3',5'-O-diacetyl-4-(1,2,4-triazol-1-yl)-2'-deoxyuridine；1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one；3′,5'-di-O-acetyl-4-(1,2,4-triazol-1-yl)-2′-deoxyuridine；[(2R,3S,5R)-3-acetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate；[(2R,3S,5R)-3-acetyloxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate
• CAS: 109025-52-7
• 化学式: C₁₅H₁₇N₅O₆
• 分子量: 363.33
• InChiKey: HEEXNJLPNPMRMG-OUCADQQQSA-N

物化性质

• 沸点：
  568.4±60.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone 在 吡啶 、 三(4-硝基苯基)磷酸酯 、 wheat shoot nucleoside phosphotransferase 、 盐酸羟胺 、 氨 作用下， 以 甲醇 、 acetate buffer 为溶剂， 反应 64.0h， 生成 1-(β-D-2-deoxyribofuranosyl)-4-hydroxyaminopyrimidin-2(1H)-one 5'-monophosphate
  参考文献：
  名称：

  5位取代的N（4）-羟基-2'-脱氧胞苷及其5'-单磷酸酯：合成，构象，与肿瘤胸苷酸合酶的相互作用以及体外抗肿瘤活性。

  摘要：

  描述了通过转化各自的5-取代的3'，5'-二-O-乙酰基-2'-来合成5-取代的N（4）-羟基-2'-脱氧胞苷5a，b，dh的简便方法。脱氧尿苷1a-c，eh。这些程序包括在位置C（4）上进行位点特异性三唑基化或N-甲基咪唑基化，然后进行羟胺化并用MeOH-NH（3）进行解封。借助于麦芽磷酸转移酶系统，将核苷5a，b，dh选择性地转化为相应的5′-单磷酸酯6a，b，dh。由（1）H NMR光谱推导并通过分子力学计算证实的D（2）O溶液中每个核苷的构象表明，戊糖环主要存在于构象S（C-2'-endo）和N（ 4）-OH基为顺式旋转异构体。研究了两种L5178Y鼠白血病细胞系对亲本和5-氟-2'-脱氧尿苷（FdUrd）的耐药性对细胞生长的抑制作用，后者对FdUrd的敏感性比前者低70倍。对于耐FdUrd的L5178Y细胞，5-氟-N（4）-羟基-2'-脱氧胞苷（5e）引起的生长抑制作用几乎是F

  DOI：

  10.1021/jm000975u
• 作为产物：
  描述：

  2-脱氧尿苷 在 吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成 1-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone
  参考文献：
  名称：

  新型核苷5'-三磷酸和含炔或氨基的亚磷酰胺的合成，用于核酸的后合成功能

  摘要：

  设计并合成了一系列新的含有炔或氨基的核苷5'-三磷酸和亚磷酰胺，用于核酸的后合成功能。为此，使用了新的3-氨基丙氧基丙炔基连接基团。它包含两种替代功能：用于氨基-炔基修饰的寡核苷酸与相应的活化酯反应的氨基和用于铜（I）催化的叠氮化物-炔烃环加成（CuAAC）反应的炔基。结果表明，可以使用多种连接新接头的方法来合成各种修饰的嘧啶核苷。

  DOI：

  10.1080/15257770.2011.595379

文献信息

• Synthesis and Applicability of Base-Discriminating DNA-Triplex-Forming¹⁹F NMR Probes
  作者：Naresh Bhuma、Ville Tähtinen、Pasi Virta

  DOI：10.1002/ejoc.201701110

  日期：2018.2.7

  N4(6-amino-2-pyridinyl)deoxycytidines were synthesized, incorporated into triplex-forming 2'-deoxyoligonucleotide strands and the applicability of the probes to recognize nucleobase content in the pyrimidine-rich strand of double helical DNA targets was evaluated. As expected, the obtained 19F NMR resonances were sensitive to the base content and unique 19F NMR-spectral fingerprints could be obtained.

  合成了 CF3 修饰的 N4（6-氨基-2-吡啶基）脱氧胞苷的亚磷酰胺结构单元，并结合到形成三链体的 2'-脱氧寡核苷酸链中，以及探针识别双螺旋富含嘧啶链中核碱基含量的适用性评估了 DNA 靶标。正如预期的那样，获得的 19F NMR 共振对碱含量很敏感，并且可以获得独特的 19F NMR 光谱指纹。
• FUNCTIONALIZATION OF PYRIMIDINE AND PURINE NUCLEOSIDES AT C4 AND C6: C-NUCLEOPHILIC SUBSTITUTION OF THEIR C4- AND C6-(1,2,4-TRIAZOL-1-YL) DERIVATIVES
  作者：Victor Timoshchuk

  DOI：10.1081/ncn-200059763

  日期：2005.4.1

  in dioxane in the presence of DBU resulting in the production of novel nucleosides 2–11. To explore the application of this methodology to purine chemistry, this approach was used to produce novel analogs from 2′-deoxyguanosine. We found that the triazolo derivative 12 undergoes C-nucleophilic substitution with nitromethane, malononitrile, acetylacetone, ethyl nitroacetate and cyanoacetate in the presence

  研究了嘧啶 C4 位和 2'-脱氧鸟苷 C6 位的 C-亲核取代以产生新型核苷，并介绍了它们各自取代产物的光谱特性。C4-(1,2,4-triazol-1-yl) 嘧啶核苷 1 用硝基烷烃、丙二腈、乙酰丙酮、硝基乙酸乙酯、乙酰乙酸乙酯和氰基乙酸乙酯在 100°C 下在二恶烷中在 DBU 存在下进行处理，从而产生新的核苷 2-11。为了探索这种方法在嘌呤化学中的应用，这种方法被用来从 2'-脱氧鸟苷生产新的类似物。我们发现三唑基衍生物 12 与硝基甲烷、丙二腈、乙酰丙酮、
• Discovery of novel N4-alkylcytidines as promising antimicrobial agents
  作者：Liudmila A. Alexandrova、Maxim V. Jasko、Sergey D. Negrya、Pavel N. Solyev、Oleg V. Shevchenko、Andrei P. Solodinin、Daria P. Kolonitskaya、Inna L. Karpenko、Olga V. Efremenkova、Alla A. Glukhova、Yuliya V. Boykova、Tatiana A. Efimenko、Natalya V. Kost、Darya A. Avdanina、Gulgina K. Nuraeva、Ivan A. Volkov、Sergey N. Kochetkov、Alexander A. Zhgun

  DOI：10.1016/j.ejmech.2021.113212

  日期：2021.4
• The Synthesis of<i>N</i>⁴-(6-Aminopyridin-2-yl)-2′-deoxycytidine for Recognizing the CG Base Pair at Neutral pH by Oligodeoxyribonucleotide-Directed Triple Helix Formation
  作者：T.-M. Chin、K.-Y. Chung、J.-J. Chen、W.-C. Lin、L.-S. Kan

  DOI：10.1002/jccs.199900103

  日期：1999.10

  AbstractThe sequence‐specific recognition of double‐helical DNA by oligodeoxyribonucleotide‐directed triple helix (triplex) formation is limited mostly to purine tracts. To interrupt the purine tract in a target sequence, a non‐natural deoxyribonucleoside N4‐(6‐aminopyridin‐2‐yl)‐2′‐deoxycytidine (pC) was designed to interact with the C base in the CG base pair. The protected phosphoramidite synthon of pC was synthesized in seven steps and then was incorporated into an oligodeoxyribonucleotide by an automatic DNA synthesizer. Two 22‐mers, designated as C2 and P, with a common sequence of 5′‐d‐TmCTXTmCTTCTGTCTCCAGACAG were synthesized in this study. mC is 5‐methyl‐2′‐deoxycytidine and X is either 2′‐deoxycytidine (C) or pC for C2 and P, respectively. C2 is able to form a paper clip type triplex with one C · CG mismatched base triad in slightly acidic conditions but not at the neutral pH. On the other hand, P forms a stable triplex under both acidic and neutral conditions. This indicates that pC is able to form a pC · CG base triad in the triplex. Their physical properties were studied by UV thermal melting experiments and circular dichorism spectroscopy (CD). The thermal melting results imply that the pC · CG base triad is as stable as the C+ · GC triad at pH 6.0, and pC helps the triplex formation preferably at neutral to acidic pH. In addition to the hydrogen bonding interaction with the CG base pair, the hydrophobic interaction of pC may also play an important role in stabilizing the triplex formation of oligodeoxyribonucleotides. In the presence of spermine at either pH 5.0 or pH 6.0, the melting temperature of the third strand of P was elevated about 30 and 21 °C, respectively. Thus, spermine can enhance the stability of the triple‐helical structure.
• Schott, Herbert; Haeussler, Markus P.; Schwendener, Reto A., Liebigs Annalen der Chemie, 1994, # 5, p. 465 - 470
  作者：Schott, Herbert、Haeussler, Markus P.、Schwendener, Reto A.

  DOI：——

  日期：——