5-butyl-2'-deoxyuridine | 57741-91-0

• 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-butyl-2'-deoxyuridine
• 英文别名: 2,4(1H,3H)-Pyrimidinedione, 5-butyl-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-；5-butyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 57741-91-0
• 化学式: C₁₃H₂₀N₂O₅
• 分子量: 284.312
• InChiKey: VIUINAIJMUWGLY-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-butyl-2'-deoxyuridine 在 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 以50%的产率得到5-n-butyl-2'-deoxyuridine 5'-monophosphate diammonium salt
  参考文献：
  名称：

  5-烷基-2'-脱氧尿苷，3'，5'-环状单磷酸酯和中性环状三酯的合成及其抗肿瘤和抗病毒特性。

  摘要：

  一系列5-烷基-2'-脱氧尿苷3'，5'-环一磷酸酯（5-R-cdUMP's，R = Et，i-Pr，n-Pr，n-Bu，n-Pent，n-Hex，与5-烷基2'-脱氧尿苷（5-R-dUrd's本身）相比，制备并在培养系统中测试了n-Oct）作为抗肿瘤和抗病毒剂。仅5-Et-和5-n-Bu-cdUMP对鼠L1210和人淋巴母细胞Raji细胞表现出明显的细胞抑制活性（ID50范围：28-82微克/ mL）。5-Et-dUrd本身更具活性（ID50 = 1.6和2.9微克/ mL）。5-i-Pr-和5-n-Bu-dUrd处于非活性状态，但对于链长为五个碳或以上的基团，活性再次提高。5-Et-cdUMP和5-Et-dUrd对脱氧胸苷激酶缺陷型（TK-）L1210和Raji细胞的活性大大降低。在涉及TK细胞的情况下，5-Et-cdUMP显然不是相应5'-单磷酸的有效前药来源。在5-R-cdUMP中

  DOI：

  10.1021/jm00154a012
• 作为产物：
  描述：

  5-(2-butenyl)-2'-deoxyuridine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以67%的产率得到5-butyl-2'-deoxyuridine
  参考文献：
  名称：

  Structural requirements of olefinic 5-substituted deoxyuridines for antiherpes activity

  摘要：

  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.

  DOI：

  10.1021/jm00363a009

文献信息

• Treatment of EBV and KHSV infection and associated abnormal cellular proliferation
  申请人：——

  公开号：US20030176392A1

  公开（公告）日：2003-09-18

  A method and composition for the treatment, prevention and/or prophylaxis of a host, and in particular, a human, infected with Epstein-Barr virus (EBV), is provided that includes administering an effective amount of a 5-substituted uracil nucleoside or its pharmaceutically acceptable salt or prodrug, optionally in a pharmaceutically acceptable diluent or excipient.

  提供了一种用于治疗、预防和/或预防寄主，特别是感染了爱泼斯坦-巴尔病毒（EBV）的人类的方法和组合物，包括向寄主施用有效量的5-取代尿嘧啶核苷或其药学上可接受的盐或前药，可选地还包括药学上可接受的稀释剂或赋形剂。
• Treatment of EBV and KHSV Infection and Associated Abnormal Cellular Proliferation
  申请人：Schinazi Raymond F.

  公开号：US20100168052A1

  公开（公告）日：2010-07-01

  A method and composition for the treatment, prevention and/or prophylaxis of a host, and in particular, a human, infected with Epstein-Barr virus (EBV), is provided that includes administering an effective amount of a 5-substituted uracil nucleoside or its pharmaceutically acceptable salt or prodrug, optionally in a pharmaceutically acceptable diluent or excipient.

  本发明提供了一种用于治疗、预防和/或预防宿主，特别是人类，感染EB病毒（EBV）的方法和组合物，其中包括在药物接受者中给予有效量的5-取代尿嘧啶核苷或其药学上可接受的盐或前药，可选地在药学上可接受的稀释剂或赋形剂中。
• Hassan, Mohamed Ezeldin, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 9, p. 1944 - 1948
  作者：Hassan, Mohamed Ezeldin

  DOI：——

  日期：——
• TREATMENT OF EBV AND KHSV INFECTION AND ASSOCIATED ABNORMAL CELLULAR PROLIFERATION
  申请人：Pharmassett Ltd.

  公开号：EP1569658A2

  公开（公告）日：2005-09-07
• EP1569658A4
  申请人：——

  公开号：EP1569658A4

  公开（公告）日：2007-05-30