1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(3-methoxyprop-1-ynyl)pyrimidine-2,4(1H,3H)-dione | 84559-00-2

• 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-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(3-methoxyprop-1-ynyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-(3-methoxypropynyl)-2'-deoxyuridine；5-(methoxymethylethynyl)-2'-deoxyuridine；2'-deoxy-5-(3-methoxyprop-1-yn-1-yl)uridine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(3-methoxyprop-1-ynyl)pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(3-methoxyprop-1-ynyl)pyrimidine-2,4-dione
• CAS: 84559-00-2
• 化学式: C₁₃H₁₆N₂O₆
• 分子量: 296.28
• InChiKey: GFTJBRNJKBKKSE-HBNTYKKESA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(3-methoxyprop-1-ynyl)pyrimidine-2,4(1H,3H)-dione 在 吡啶 、 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[5-(3-methoxy-prop-1-ynyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Synthesis and DNA Duplex Stabilities of Oligonucleotides Containing C-5-(3-Methoxypropynyl)-2′-deoxyuridine Residues

  摘要：

  5'-Dimethoxytrityl-5-(3-methoxypropynyl)-2'-deoxyuridine phosphoroamidite was synthesized with the use of commercial 3-methoxypropyne. Oligonucleotides (ODNs) containing 5-(3-methoxypropynyl)-2'-deoxyuridine in different positions were prepared. The stabilities of the duplexes formed by these ODNs with the complementary templates are increased in comparison with the unmodified counterparts. On average modified residue incorporated, the Tm is raised by 1 degrees C.

  DOI：

  10.1080/07328319708001343
• 作为产物：
  描述：

  碘苷 在 copper(l) iodide 、 四(三苯基膦)钯 吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-5-(3-methoxyprop-1-ynyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Oligodeoxynucleotides incorporating structurally simple 5-alkynyl-2′-deoxyuridines fluorometrically respond to hybridization

  摘要：

  研究表明，2â²-脱氧尿苷的精选 5- 乙炔基衍生物可对杂交产生荧光反应，并在保持双链稳定性的同时选择性地与腺嘌呤碱基配对。

  DOI：

  10.1039/b705805e

文献信息

• Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides
  作者：Erik De Clercq、Johan Descamps、Jan Balzarini、Jerzy Giziewicz、Philip J. Barr、Morris J. Robins

  DOI：10.1021/jm00359a008

  日期：1983.5

  5-alkynyl-2'-deoxyuridine nucleosides. The 5-ethynyl, followed by 5-propynyl, products had the highest antiviral potency, with the 2'-deoxy derivatives being more effective than the arabinosyl compounds. Activity was weak at hexynyl and disappeared at heptynyl. Inclusion of an omega-hydroxy function diminished the antiviral effect. None of the 5-alkynyluracil nucleosides tested had sufficient selectivity

  末端炔与5-碘-1-（2,3,5-三-Op-甲苯基-β-D-阿拉伯呋喃糖基）尿嘧啶和5-碘-3'，5'-二-Op-甲苯基-2'的偶联-脱氧尿苷在三乙胺中易于催化量的双（三苯基膦）-钯（II）氯化物和碘化铜（I）进行。使所得产物脱保护，得到5-炔基-1-β-D-阿拉伯呋喃糖基尿嘧啶和5-炔基-2'-脱氧尿苷核苷。5-乙炔基，其次是5-丙炔基，产品具有最高的抗病毒效力，其中2'-脱氧衍生物比阿拉伯糖基化合物更有效。活性在己炔基处弱，而在庚炔基处消失。包含ω-羟基功能减弱了抗病毒作用。测试的5-炔基尿嘧啶核苷均没有足够的选择性足以胜任候选抗病毒药。
• Organometallic Nucleosides: Synthesis and Biological Evaluation of Substituted Dicobalt Hexacarbonyl 2′‐Deoxy‐5‐oxopropynyluridines
  作者：Renata Kaczmarek、Dariusz Korczyński、Karolina Królewska‐Golińska、Kraig A. Wheeler、Ferman A. Chavez、Agnieszka Mikus、Roman Dembinski

  DOI：10.1002/open.201700168

  日期：2018.3

  Reactions of dicobalt octacarbonyl [Co2(CO)8] with 2′‐deoxy‐5‐oxopropynyluridines and related compounds gave dicobalt hexacarbonyl nucleoside complexes (83–31 %). The synthetic outcomes were confirmed by X‐ray structure determination of dicobalt hexacarbonyl 2′‐deoxy‐5‐(4‐hydroxybut‐1‐yn‐1‐yl)uridine, which exhibits intermolecular hydrogen bonding between a modified base and ribose. The electronic structure

  八羰基二钴 [Co 2 (CO) 8 ] 与 2'-脱氧-5-氧代丙炔尿苷及相关化合物反应，得到六羰基二钴核苷复合物 (83-31%)。合成结果通过六羰基二钴 2'-脱氧-5-(4-羟基丁-1-yn-1-基)尿苷的 X 射线结构测定得到证实，其在修饰的碱基和核糖之间表现出分子间氢键。通过 DFT 计算表征了该化合物的电子结构。检查了有机金属核苷对 HeLa 和 K562 癌细胞系的生长抑制作用，并与炔基核苷前体的抑制作用进行了比较。二钴羰基部分与 2'-脱氧-5-炔基尿苷的配位导致细胞毒性效力显着增加。钴化合物表现出抗增殖活性，对 HeLa 细胞系的中值抑制值 (IC 50 ) 在 20 至 80 μm范围内，对 K562 细胞系在 18 至 30 μm范围内。通过使用 1,1-双（二苯基膦）甲烷 (dppm) 配体扩大了乙酰基取代的钴核苷的配位，该配体表现出相当水平的细胞毒性。在 K562
• Oligodeoxynucleotides incorporating structurally simple 5-alkynyl-2′-deoxyuridines fluorometrically respond to hybridization
  作者：Robert H. E. Hudson、Arash Ghorbani-Choghamarani

  DOI：10.1039/b705805e

  日期：——

  Selected 5-ethynyl derivatives of 2′-deoxyuridine are shown to fluorometrically respond to hybridization and selectively base-pair to adenine whilst maintaining duplex stability.

  研究表明，2â²-脱氧尿苷的精选 5- 乙炔基衍生物可对杂交产生荧光反应，并在保持双链稳定性的同时选择性地与腺嘌呤碱基配对。
• Synthesis and DNA Duplex Stabilities of Oligonucleotides Containing C-5-(3-Methoxypropynyl)-2′-deoxyuridine Residues
  作者：Vladimir V. Tolstikov、Dmitry A. Stetsenko、Victor K. Potapov、Eugene D. Sverdlov

  DOI：10.1080/07328319708001343

  日期：1997.3

  5'-Dimethoxytrityl-5-(3-methoxypropynyl)-2'-deoxyuridine phosphoroamidite was synthesized with the use of commercial 3-methoxypropyne. Oligonucleotides (ODNs) containing 5-(3-methoxypropynyl)-2'-deoxyuridine in different positions were prepared. The stabilities of the duplexes formed by these ODNs with the complementary templates are increased in comparison with the unmodified counterparts. On average modified residue incorporated, the Tm is raised by 1 degrees C.