5-methylselenyl-methyl-2'-deoxy uridine | 1276113-52-0

• 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-methylselenyl-methyl-2'-deoxy uridine
• 英文别名: 5-methylselenylmethyl-2'-deoxyuridine；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(methylselanylmethyl)pyrimidine-2,4-dione
• CAS: 1276113-52-0
• 化学式: C₁₁H₁₆N₂O₅Se
• 分子量: 335.218
• InChiKey: IORLQYCOQAFCHT-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.57
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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-methylselenyl-methyl-2'-deoxy uridine 在 sodium periodate 作用下， 以 water-d2 为溶剂， 反应 120.0h， 生成 (S)-9-benzyl-1-butyl-3-((S)-cyclohexyl(hydroxy)methyl)-1,4,9-triazaspiro[5.5]undecane-2,5-dione 、 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylene-6-((methylselanyl)oxy)dihydropyrimidine-2,4(1H,3H)-dione 、 5-羟甲基脱氧尿苷
  参考文献：
  名称：

  Potent radiosensitizing agents: 5-Methylselenyl- and 5-phenylselenyl-methyl-2′-deoxyuridine

  摘要：

  This Letter describes the novel radiosensitizing agents based on nucleoside base modification. In addition to the known 5-phenylselenide derivative, 5-methylselenide modified thymidine, which has a van der Waals radius smaller than the phenyl group, was newly synthesized. The similar monomer activity of 5-methylselenide derivative under oxidation condition was confirmed by NMR experiments. The cytotoxicity tests and radiosensitizing experiments of both compounds were carried out using the H460 lung cancer cell line. Both the 5-phenylselenide and the 5-methylselenide derivatives showed a relatively low toxicity to the cells. However, in combination with gamma-radiolysis, both exerted good radiosensitizing effects to the lung cancer cell lines in vitro. This result confirms that 5-methylselenide modified thymidine could be a useful candidate as a potential radiosensitizing agent in vivo. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.102
• 作为产物：
  描述：

  3,5-双-O-乙酰胸苷 在 ammonium hydroxide 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 26.5h， 生成 5-methylselenyl-methyl-2'-deoxy uridine
  参考文献：
  名称：

  NOVEL SELENY-METHYLURACIL COMPOUNDS, RADIOSENSITIZER AND PHARMACEUTICAL COMPOSITION USING THEM

  摘要：

  提供了一种新的硒基甲基尿嘧啶化合物和一种用于增强放射治疗效果的药物组合物。该组合物包含至少一种从硒基甲基尿嘧啶化合物或其药学上可接受的盐中选择的活性成分。

  公开号：

  US20130211067A1

文献信息

• NOVEL SELENY-METHYLURACIL COMPOUNDS, RADIOSENSITIZER AND PHARMACEUTICAL COMPOSITION USING THEM
  申请人：Hong In Seok

  公开号：US20130211067A1

  公开（公告）日：2013-08-15

  Provided are novel selenyl-methyluracil compounds and a pharmaceutical composition for enhancing the effect of radiation treatment. The composition contains at least one compound selected from the group consisting of the selenyl-methyluracil compounds or pharmaceutically acceptable salts thereof, as an active ingredient.

  提供了一种新的硒基甲基尿嘧啶化合物和一种用于增强放射治疗效果的药物组合物。该组合物包含至少一种从硒基甲基尿嘧啶化合物或其药学上可接受的盐中选择的活性成分。
• Potent radiosensitizing agents: 5-Methylselenyl- and 5-phenylselenyl-methyl-2′-deoxyuridine
  作者：Ambadas B. Rode、Byeong Mo Kim、Seon Hwa Park、In Seok Hong、Sung Hee Hong

  DOI：10.1016/j.bmcl.2010.12.102

  日期：2011.2

  This Letter describes the novel radiosensitizing agents based on nucleoside base modification. In addition to the known 5-phenylselenide derivative, 5-methylselenide modified thymidine, which has a van der Waals radius smaller than the phenyl group, was newly synthesized. The similar monomer activity of 5-methylselenide derivative under oxidation condition was confirmed by NMR experiments. The cytotoxicity tests and radiosensitizing experiments of both compounds were carried out using the H460 lung cancer cell line. Both the 5-phenylselenide and the 5-methylselenide derivatives showed a relatively low toxicity to the cells. However, in combination with gamma-radiolysis, both exerted good radiosensitizing effects to the lung cancer cell lines in vitro. This result confirms that 5-methylselenide modified thymidine could be a useful candidate as a potential radiosensitizing agent in vivo. (c) 2011 Elsevier Ltd. All rights reserved.