1-(4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(1H-naphtho[2,3-d]imidazol-2-yl)pyrimidine-2,4(1H,3H)-dione | 1354943-60-4

• 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: 1-(4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(1H-naphtho[2,3-d]imidazol-2-yl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-(1H-naphtho[2,3-d]imidazol-2-yl)-2'-deoxyuridine；5-(1H-benzo[f]benzimidazol-2-yl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1354943-60-4
• 化学式: C₂₀H₁₈N₄O₅
• 分子量: 394.387
• InChiKey: TXHJMXQXNYIQNA-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 2,6-二甲基吡啶 、 dipotassium peroxodisulfate 、 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 水 、 sodium hydrogensulfite 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 3.03h， 生成 1-(4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(1H-naphtho[2,3-d]imidazol-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Efficient microwave-assisted synthesis, antibacterial activity and high fluorescence of 5 benzimidazolyl-2′-deoxyuridines

  摘要：

  A series of novel C-5 benzimidazolyl-2'-deoxyuridines was synthesized in good yields under solvent-free conditions and microwave irradiation from 5-formyl-2'-deoxyuridine and arylenediamine derivatives in the presence of NaHSO3 as catalyst. Their absorption and fluorescence spectra were measured. They showed intense fluorescence around 400-500 nm with quantum yields between 0.3 and 0.5. All compounds studied in this work were screened for their antibacterial activities against a series of Gram positive and negative bacteria. The trifluoromethyl substituted benzimidazole derivatives showed some antibacterial activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.041

文献信息

• Synthesis and spectroscopic properties of fluorescent 5-benzimidazolyl-2′-deoxyuridines 5-fdU probes obtained from o-phenylenediamine derivatives
  作者：Pu Guo、Xiaowei Xu、Xiaoyu Qiu、Yimin Zhou、Shengyong Yan、Changcheng Wang、Chunjiang Lu、Wen Ma、Xiaocheng Weng、Xianzheng Zhang、Xiang Zhou

  DOI：10.1039/c3ob27519a

  日期：——

  Fluorescent nucleosides (dUbmz) with desirable fluorescence quantum yield (Φ) are synthesized from almost non-fluorescent 5-fdU and o-phenylenediamine derivatives. The fluorescence of these nucleosides is quite sensitive to pH and organic solvents. 4-Methoxybenzene-1,2-diamine was used for the detection of 5-fdU among natural nucleosides.

  合成了具有理想荧光量子产率（Φ）的荧光核苷（dUbmz），其来源于几乎不发光的5-fdU和邻苯二胺衍生物。这些核苷的荧光对pH值和有机溶剂相当敏感。4-甲氧基苯-1,2-二胺被用于在天然核苷中检测5-fdU。