5-(3-phenylisoxazol-5-yl)-2'-deoxyuridine | 133070-83-4

• 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-(3-phenylisoxazol-5-yl)-2'-deoxyuridine
• 英文别名: 1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-(3-phenyl-isoxazol-5-yl)-1H-pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(3-phenyl-1,2-oxazol-5-yl)pyrimidine-2,4-dione
• CAS: 133070-83-4
• 化学式: C₁₈H₁₇N₃O₆
• 分子量: 371.349
• InChiKey: OMVJZCCMNRCBRW-NUEKZKHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(2R,3S,5R)-3-acetyloxy-5-[2,4-dioxo-5-(3-phenyl-1,2-oxazol-5-yl)pyrimidin-1-yl]oxolan-2-yl]methyl acetate 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 5-(3-phenylisoxazol-5-yl)-2'-deoxyuridine
  参考文献：
  名称：

  C5-Modified nucleosides exhibiting anticancer activity

  摘要：

  We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2'deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2'-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2'-deoxyuridine provided triazole derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.072

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，
• 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：——
• C5-Modified nucleosides exhibiting anticancer activity
  作者：Yoon-Suk Lee、Sun Min Park、Hwan Mook Kim、Song-Kyu Park、Kiho Lee、Chang Woo Lee、Byeang Hyean Kim

  DOI：10.1016/j.bmcl.2009.06.072

  日期：2009.8

  We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2'deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2'-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2'-deoxyuridine provided triazole derivatives. (C) 2009 Elsevier Ltd. All rights reserved.