5-(benzothiazol-2-yl)-2'-deoxyuridine

• 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-(benzothiazol-2-yl)-2'-deoxyuridine
• 英文别名: 5-(1,3-benzothiazol-2-yl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₁₆H₁₅N₃O₅S
• 分子量: 361.378
• InChiKey: BLEJGMGHPULIOW-DMDPSCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  双(2-氨基苯基)二硫 在 1,4-dithio-D,L-threitol 、 双氧水 、 氧气 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 5-(benzothiazol-2-yl)-2'-deoxyuridine
  参考文献：
  名称：

  5-（5,6-二甲氧基苯并噻唑-2-基）-2'-脱氧尿苷（dbtU）和含有dbtU的寡脱氧核糖核苷酸的荧光性质

  摘要：

  描述了11个含d bt U的5–（苯并噻唑-2-基）-2 -'-脱氧尿苷衍生物和寡脱氧核糖核苷酸（ODN）的光物理性质。比较了包含5'-X bt U-3'和5'- bt UY-3'的16种组合的ODN的荧光特性，发现d bt U是一种非常有前途的新荧光类似物，但对Dbt U的敏感性较低。它在DNA中的微环境。

  DOI：

  10.1002/ejoc.201100818

文献信息

• Synthesis of fluorescent 5-heteroarylpyrimidine-containing oligonucleotides <i>via</i> post-synthetic trifluoromethyl conversion
  作者：Yuta Ito、Hisato Tanaka、Ayana Murakami、Yasufumi Fuchi、Yoshiyuki Hari

  DOI：10.1039/d4ob00402g

  日期：——

  base in DNA oligonucleotides was achieved. Specifically, the oligonucleotides containing 5-trifluoromethylpyrimidine bases were treated with o-phenylenediamines and o-aminothiophenols as nucleophiles to afford the corresponding 5-(benzimidazol-2-yl)- and 5-(benzothiazol-2-yl)-pyrimidine-modified bases. Furthermore, evaluation of the fluorescence properties of the obtained oligonucleotides revealed that

  实现了DNA寡核苷酸中嘧啶碱基C5位置上的三氟甲基到杂芳基的合成后转化。具体地，用邻苯二胺和邻氨基苯硫酚作为亲核试剂处理含有5-三氟甲基嘧啶碱基的寡核苷酸，得到相应的5-(苯并咪唑-2-基)-和5-(苯并噻唑-2-基)-嘧啶修饰的碱基。此外，对所获得的寡核苷酸的荧光特性进行评估表明，其中含有5-(5-甲基苯并咪唑-2-基)胞嘧啶的寡核苷酸显示出最高的荧光强度。这些结果表明，合成后三氟甲基转化实用且操作简单，是探索功能性寡核苷酸的有力工具。
• Synthesis and in vitro antileishmanial activity of 5-substituted-2′-deoxyuridine derivatives
  作者：Corinne Peyron、Rachid Benhida、Christian Bories、Philippe M. Loiseau

  DOI：10.1016/j.bioorg.2005.07.001

  日期：2005.12

  We report herein the synthesis and the in vitro antileishmanial evaluation of 5-substituted-2'-deoxyuridine nucleosides. The most active compound against Leishmania donovani promastigotes was Thia-dU (3a) with an IC50 = 3 mu M. This compound exhibited the same activity as zidovudine (3'-azido-2'-deoxythymidine) used as nucleoside reference compound. Considering the cytotoxicity of synthetic compounds on peritoneal murine macrophages., the most toxic compound was MeThio-dU (3d) with a MTC at 10 mu M. Only Methia-dU (3b) was active against intramacrophagic amastigotes with an IC50 = 6.5 mu M. This latter can now be evaluated in vivo, for further investigations through structure-based drug design. (c) 2005 Elsevier Inc. All rights reserved.
• Fluorescence Properties of 5-(5,6-Dimethoxybenzothiazol-2-yl)-2′-deoxyuridine (dbtU) and Oligodeoxyribonucleotides Containing dbtU
  作者：Wataru Hirose、Kousuke Sato、Akira Matsuda

  DOI：10.1002/ejoc.201100818

  日期：2011.11

  The photophysical properties of 11 substituted 5‐(benzothiazol‐2‐yl)‐2′‐deoxyuridine derivatives and oligodeoxyribonucleotides (ODNs) containing dbtU are described. The fluorescence properties of the ODNs containing 16 combinations of 5′‐XbtU‐3′ and 5′‐btUY‐3′ were compared, and dbtU was found to be a very promising new fluorescent analogue while showing low sensitivity to its microenvironment in DNA

  描述了11个含d bt U的5–（苯并噻唑-2-基）-2 -'-脱氧尿苷衍生物和寡脱氧核糖核苷酸（ODN）的光物理性质。比较了包含5'-X bt U-3'和5'- bt UY-3'的16种组合的ODN的荧光特性，发现d bt U是一种非常有前途的新荧光类似物，但对Dbt U的敏感性较低。它在DNA中的微环境。