5-Ethynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine | 69075-43-0

• 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: 5-Ethynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine
• 英文别名: Uridine, 2a(2)-deoxy-5-ethynyl-, 3a(2),5a(2)-bis(4-methylbenzoate)；[(2R,3S,5R)-5-(5-ethynyl-2,4-dioxopyrimidin-1-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 69075-43-0
• 化学式: C₂₇H₂₄N₂O₇
• 分子量: 488.497
• InChiKey: ZDONZNXPUOWSJE-YTFSRNRJSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  5-Ethynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine 在 palladium on activated charcoal N-羟基丁二酰亚胺 、 sodium azide 、 四溴化碳 、 氢气 、 sodium methylate 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~60.0 ℃ 、300.01 kPa 条件下， 反应 12.25h， 生成 {[10-(10-{[5-ethyl-2',5'-dideoxyuridine-5'-methyl]-carbamoyl}-decylcarbamoyl)-decyl]-methoxycarbonylmethyl-amino}-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis of tricarbonyl rhenium and technetium complexes of a 5′-carboxamide 5-ethyl-2′-deoxyuridine for selective inhibition of herpes simplex virus thymidine kinase 1

  摘要：

  Herpes simplex virus thymidine kinase type 1 (HSV1-TK) is frequently used as reporter protein in gene therapy. Our aim is to produce single photon emitting reporter probe based on technetium-99m. The synthesis of organometallic technetium and rhenium complexes of a 5'-carboxamide 5-ethyl-2'-deoxyuridine derivative able to selectively inhibit HSV1-TK is presented. The 5-ethyl-2'-deoxyuridine functionalized with a suitable tridentate chelating system at position 5' was synthesized from commercial 2'-deoxyuridine in seven steps. The 5-ethyl-2'-deoxyuridine derivative was labeled with the fac-M(CO)(3)-core (M = Tc, Re). The resulting rhenium complex was found to be a selective competitive inhibitor of HSV1-TK (K-i = 4.56 mu M). Inhibition of the human cytosolic thymidine kinase (hTK1) previously reported with organometallic rhenium and technetium complexes of 5'-carboxamide thymidine derivative was not observed. The uptake of the technetium-99m complex in transfected cells expressing HSV1-TK has been evaluated to assess its possible use as reporter. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.10.011
• 作为产物：
  描述：

  5-iodo-3',5'-di-O-p-toluyl-2'-deoxyuridine 在 (PPh₃)PdCl₂ potassium fluoride 、 copper(l) iodide 、 四乙基溴化铵 作用下， 以 三乙胺 、 乙腈 为溶剂， 反应 19.0h， 生成 5-Ethynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of tricarbonyl rhenium and technetium complexes of a 5′-carboxamide 5-ethyl-2′-deoxyuridine for selective inhibition of herpes simplex virus thymidine kinase 1

  摘要：

  Herpes simplex virus thymidine kinase type 1 (HSV1-TK) is frequently used as reporter protein in gene therapy. Our aim is to produce single photon emitting reporter probe based on technetium-99m. The synthesis of organometallic technetium and rhenium complexes of a 5'-carboxamide 5-ethyl-2'-deoxyuridine derivative able to selectively inhibit HSV1-TK is presented. The 5-ethyl-2'-deoxyuridine functionalized with a suitable tridentate chelating system at position 5' was synthesized from commercial 2'-deoxyuridine in seven steps. The 5-ethyl-2'-deoxyuridine derivative was labeled with the fac-M(CO)(3)-core (M = Tc, Re). The resulting rhenium complex was found to be a selective competitive inhibitor of HSV1-TK (K-i = 4.56 mu M). Inhibition of the human cytosolic thymidine kinase (hTK1) previously reported with organometallic rhenium and technetium complexes of 5'-carboxamide thymidine derivative was not observed. The uptake of the technetium-99m complex in transfected cells expressing HSV1-TK has been evaluated to assess its possible use as reporter. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.10.011

文献信息

• Synthesis and antiviral activity of 5-heteroaryl-substituted 2'-deoxyuridines
  作者：P. Wigerinck、R. Snoeck、P. Claes、E. De Clercq、P. Herdewijn

  DOI：10.1021/jm00110a003

  日期：1991.6

  The synthesis of 5-heteroaryl-substituted 2'-deoxyuridines is described. The heteroaromatics were obtained from three different 5-substituted 2'-deoxyuridines. Cycloaddition reaction of nitrile oxides on the 5-ethynyl derivative 1 gave the isoxazoles 4a-e. The thiazole derivatives 14a-c were obtained from the 5-thiocarboxamide 11, while 5-pyrrol-1-yl-2'-deoxyuridine (17) could be synthesized directly

  描述了5-杂芳基取代的2'-脱氧尿苷的合成。杂芳族化合物获自三种不同的5-取代的2'-脱氧尿苷。腈氧化物在5-乙炔基衍生物1上的环加成反应得到异恶唑4a-e。噻唑衍生物14a-c从5-硫代羧酰胺11获得，而5-吡咯-1-基-2'-脱氧尿苷（17）可以直接从5-氨基-2'-脱氧尿苷合成。评价化合物的抗病毒活性。注意到针对5-（3-溴异x唑-5-基）-2'-脱氧尿苷（4c）的针对1型单纯疱疹病毒（HSV-1）和水痘带状疱疹病毒（VZV）的选择性活性。该化合物对单纯疱疹病毒2型，巨细胞病毒和缺乏胸腺嘧啶激酶（TK）的HSV-1和VZV突变体无活性，这表明最有可能的是，
• Brønsted acid-mediated cascade cyclization of 2-propynolphenols/anilines leading to 4-halo-2H-chromenes and 1,2-dihydroquinolines
  作者：Ren Li、Xian-Rong Song、Xi Chen、Haixin Ding、Qiang Xiao、Yong-Min Liang

  DOI：10.1016/j.tetlet.2017.06.064

  日期：2017.8

  A convenient strategy is present for easy construction of a series of 4-halo-2H-chromenes and 1,2-dihydroquinolines through Brønsted acid-mediated cascade cyclization of readily accessible 2-propynolphenols/anilines. Our developed approaches prove have good functional-group applicabilities and could be enlarged to gram quantities in high yields. Moreover, the resulting halides could be further exploited

  目前存在一种方便的策略，可通过布朗斯台德酸介导的易于获得的2-丙炔酚/苯胺的级联环化，轻松构建一系列的4-卤代2 H-苯甲基和1,2-二氢喹啉。我们开发的方法证明具有良好的官能团适用性，并且可以高产量地扩大到克量。此外，所得的卤化物可在随后的钯催化的偶联反应中进一步利用。
• Nucleic acid related compounds. 39. Efficient conversion of 5-iodo to 5-alkynyl and derived 5-substituted uracil bases and nucleosides
  作者：Morris J. Robins、Philip J. Barr

  DOI：10.1021/jo00159a012

  日期：1983.6
• Antiviral compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0208550B1

  公开（公告）日：1991-05-22
• WIGERINCK, P.;SNOECK, R.;CLAES, P.;DE, CLERCQ E.;HERDEWIJN, P., J. MED. CHEM., 34,(1991) N, C. 1767-1772
  作者：WIGERINCK, P.、SNOECK, R.、CLAES, P.、DE, CLERCQ E.、HERDEWIJN, P.

  DOI：——

  日期：——