2'-脱氧-5-碘尿苷3'，5'-二苯甲酸酯 | 4833-07-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 2'-脱氧-5-碘尿苷3'，5'-二苯甲酸酯
• 英文名称: 3',5'-di-O-benzoyl-5-iodo-2'-deoxyuridine
• 英文别名: ((2R,3S,5R)-3-(Benzoyloxy)-5-(5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl benzoate；[(2R,3S,5R)-3-benzoyloxy-5-(5-iodo-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 4833-07-2
• 化学式: C₂₃H₁₉IN₂O₇
• 分子量: 562.318
• InChiKey: UMRXVIVKRFANLA-IPMKNSEASA-N

物化性质

• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-脱氧-5-碘尿苷3'，5'-二苯甲酸酯 在 potassium fluoride 、 copper(l) iodide 、 四乙基溴化铵 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.0h， 生成 2'-Deoxy-3',5'-di-O-benzoyl-5-ethynyluridine
  参考文献：
  名称：

  Synthesis of carboranes containing nucleoside bases. Unexpectedly high cytostatic and cytocidal toxicity towards cancer cells

  摘要：

  已制备了5-碳硼烷尿苷1、5-碳硼烷脱氧尿苷2和5-羟甲基碳硼烷尿苷3，它们对癌细胞显示出出乎意料的高细胞毒性，IC50值约为10-5摩尔/立方分米。

  DOI：

  10.1039/c39920000157
• 作为产物：
  描述：

  2-脱氧尿苷 在 吡啶 、 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2'-脱氧-5-碘尿苷3'，5'-二苯甲酸酯
  参考文献：
  名称：

  钯催化的三氟异丙烯基锌试剂与乙烯基卤化物的交叉偶联。三氟甲基化的1，3-二烯的新型立体特异性

  摘要：

  通过钯催化三氟异丙烯基锌试剂与乙烯基卤化物的交叉偶联，高产率地立体合成了含有CF 3-基团的1，3-二烯。一种新颖的CF 3含核苷，5-（α-CF 3 -乙烯基）-2'-脱氧尿苷（6）通过这种方法制备。

  DOI：

  10.1016/s0040-4039(00)93982-0

文献信息

• η⁶-(Arene)tricarbonylchromium and Manganese Complexes Linked to 2‘-Deoxyuridine
  作者：Mélanie Etheve-Quelquejeu、Jean-Philippe Tranchier、Françoise Rose-Munch、Eric Rose、Lieve Naesens、Erik De Clercq

  DOI：10.1021/om700674v

  日期：2007.11.1

  Synthesis of η6-(arene)tricarbonylchromium and manganese complexes linked to 2‘-deoxyuridine via a triple-bond spacer is reported using palladium-catalyzed reactions of alkynes with halogeno derivatives, and their antiviral activity in cell-based assays studied.

  η的合成6 - （芳烃）tricarbonylchromium并经由三键间隔使用炔烃的钯催化的反应与卤代衍生物被报告链接到-2'-脱氧尿苷锰配合物，并在基于细胞的测定它们的抗病毒活性的研究。
• Palladium(0)/Copper(I)-Cocatalyzed Cross-Coupling of the Zinc Reagent of Ethyl 3-Bromo-3,3-difluoropropionate with Aryl (Alkenyl) Halides:  An Efficient Stereoselective Synthesis of β-Fluoro-α,β-unsaturated Esters
  作者：Sheng Peng、Feng-Ling Qing、Yi-Qun Li、Chang-Ming Hu

  DOI：10.1021/jo991276w

  日期：2000.2.1

  Na2S2O4 initiation, followed by oxidation of the acetal with Caro acid. The treatment of 1 with active zinc dust in anhydrous DMF at room temperature produced the zinc reagent ZnBrCF2CH2CO2C2H5 (2). The cross coupling of the zinc reagent 2 with aryl (alkenyl) halides (R−X) in DMF using Pd(0)−Cu(I) as cocatalyst stereoselectively provided the β-fluoro-α,β-unsaturated esters (RCFCHCO2C2H5 4) directly and

  3-溴-3, 3-二氟丙酸乙酯 (1) 在 Na2S2O4 引发下将二溴二氟甲烷自由基加成到乙基乙烯基醚中，然后用胡萝卜酸氧化缩醛，以 75% 的总产率制备。在室温下用无水 DMF 中的活性锌粉处理 1 产生锌试剂 ZnBrCF2CH2CO2C2H5 (2)。使用 Pd(0)-Cu(I) 作为助催化剂，锌试剂 2 与芳基（烯基）卤化物 (R-X) 在 DMF 中的交叉偶联立体选择性地提供了 β-氟代-α,β-不饱和酯 (RCFCHCO2C2H5 4)直接和中等产量。观察到范围从 3:2 到 1:0 的 E/Z 比。这是Cu(I)可以提高交叉偶联反应选择性的第一个例子。
• 5-(E)-bromovinyl uracil analogues and related pyrimidine nucleosides as anti-viral agents and methods of use
  申请人：——

  公开号：US20040053891A1

  公开（公告）日：2004-03-18

  The present invention relates to pyrimidine nucleoside compounds and their use to treat viral infections of Varicella Zoster Virus, Epstein Barr Virus and Kaposi's Sarcoma virus, also known as HV-8 and related complications of these viral infections. In another aspect of the present invention, the use of one or more nucleoside compound to increase the retention or half-life of 5-fluorouracil (FU) in patients is also described.

  本发明涉及嘧啶核苷化合物及其用于治疗水痘-带状疱疹病毒、艾普斯坦-巴尔病毒和卡波西肉瘤病毒等病毒感染及其相关并发症的应用。在本发明的另一方面，还描述了使用一种或多种核苷化合物以增加5-氟尿嘧啶（FU）在患者体内的保留时间或半衰期。
• Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity
  作者：John Goodchild、Roderick A. Porter、Robert H. Raper、Iain S. Sim、Roger M. Upton、Julie Viney、Harry J. Wadsworth

  DOI：10.1021/jm00363a009

  日期：1983.9

  A number of structurally related 5-substituted pyrimidine 2'-deoxyribonucleosides were synthesized and tested for antiviral activity against herpes simplex virus type 1 (HSV-1) in cell culture. A minimum inhibitory concentration was determined for each compound, and from a comparison of these values a number of conclusions were drawn with regard to those molecular features that enhance or reduce antiviral activity. Optimum inhibition of HSV-1 in cell culture occurred when the 5-substituent was unsaturated and conjugated with the pyrimidine ring, was not longer than four carbon atoms in length, had E stereochemistry, and included a hydrophobic, electronegative function but did not contain a branching point. Such features are contained in (E)-5-(2-bromovinyl)-2'-deoxyuridine, which was the most active of the compounds described.
• Synthesis and Excited-State Properties of a Novel Ruthenium Nucleoside:  5-[Ru(bpy)₂(4-m-4‘-pa-bpy)]²⁺-2‘-deoxyuridine
  作者：Shoeb I. Khan、Amy E. Beilstein、Gregory D. Smith、Milan Sykora、Mark W. Grinstaff

  DOI：10.1021/ic990067r

  日期：1999.5.1

  The synthesis and photophysical properties of a novel ruthenium-modified nucleoside are reported. The key synthetic step to 5-[Ru(bpy)2(4-m-4'-pa-bpy)](2+)-2'-deoxyuridine involves the Pd(0)-catalyzed cross-coupling of a propargylamine-derivatized Ru(bpy)(3)(2+) and 3',5'-dibenzoyloxy-2'-deoxy-5-iodouridine. The long-lived (MLCT)-M-3 excited state (1300 ns) of 5-[Ru(bpy)(2)(4-m-4'-pa-bpy)](2+)-2'-deoxyuridine has an emission maximum centered at 640 nm.; Step-scan Fourier transform infrared ((SFTIR)-F-2) time-resolved spectroscopy reveals the excited-state electron to be localized on the modified bipyridine with the excited-state dipole oriented toward the 2'-deoxyuridine.