1-[(2-acetoxyethoxy)methyl]-5-(m-toluoylethynyl)uracil | 249509-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(2-acetoxyethoxy)methyl]-5-(m-toluoylethynyl)uracil
• 英文别名: 2-[[5-[3-(3-Methylphenyl)-3-oxoprop-1-ynyl]-2,4-dioxopyrimidin-1-yl]methoxy]ethyl acetate
• CAS: 249509-39-5
• 化学式: C₁₉H₁₈N₂O₆
• 分子量: 370.362
• InChiKey: LOIYBTXTLCFTCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[(2-acetoxyethoxy)methyl]-5-(m-toluoylethynyl)uracil 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以89%的产率得到1-[(2-hydroxyethoxy)methyl]-5-(m-toluoylethynyl)uracil
  参考文献：
  名称：

  5-(Acylethynyl)uracils, 5-(Acylethynyl)-2'-deoxyuridines and 5-(Acylethynyl)-1-(2-hydroxyethoxy)methyluracils. Their synthesis, antiviral and cytotoxic activities11Part 25 of our series of studies on uracil derivatives and analogues. For part 24, see [1]

  摘要：

  5-(acylethynyl)uracils 4 were synthesized from 5-iodo-2,4-dimethoxypyrimidine 1 through a palladium-catalyzed reaction with acetylenic carbinols 5, subsequent oxidation with manganese dioxide in dichloromethane, demethylation with 6 N hydrochloric acid, followed by treatment with sodium hydroxide in 95% ethanol. The corresponding 5-acylethynyl-2'-deoxyuridines 9 and 5-acylethynyl-1-(2-hydroxyethoxy-methyl)uracils 13 were synthesized following a similar procedure. The 5-acylethynyluracils 4 were cytotoxic against murine L1210 and human T-lymphocyte (Molt 4/C8, GEM) cells. The 2'-deoxyuridine derivatives 9 were less cytotoxic; however the acyclonucleosides 13 were as active as the free bases 4. The compounds did not have antiviral activities at subtoxic concentrations. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80088-9
• 作为产物：
  描述：

  1-[(2-acetoxyethoxy)methyl]-5-iodouracil 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[(2-acetoxyethoxy)methyl]-5-(m-toluoylethynyl)uracil
  参考文献：
  名称：

  5-(Acylethynyl)uracils, 5-(Acylethynyl)-2'-deoxyuridines and 5-(Acylethynyl)-1-(2-hydroxyethoxy)methyluracils. Their synthesis, antiviral and cytotoxic activities11Part 25 of our series of studies on uracil derivatives and analogues. For part 24, see [1]

  摘要：

  5-(acylethynyl)uracils 4 were synthesized from 5-iodo-2,4-dimethoxypyrimidine 1 through a palladium-catalyzed reaction with acetylenic carbinols 5, subsequent oxidation with manganese dioxide in dichloromethane, demethylation with 6 N hydrochloric acid, followed by treatment with sodium hydroxide in 95% ethanol. The corresponding 5-acylethynyl-2'-deoxyuridines 9 and 5-acylethynyl-1-(2-hydroxyethoxy-methyl)uracils 13 were synthesized following a similar procedure. The 5-acylethynyluracils 4 were cytotoxic against murine L1210 and human T-lymphocyte (Molt 4/C8, GEM) cells. The 2'-deoxyuridine derivatives 9 were less cytotoxic; however the acyclonucleosides 13 were as active as the free bases 4. The compounds did not have antiviral activities at subtoxic concentrations. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80088-9

文献信息

• Unusual cytotoxicities of 5-(acylethynyl)-1-(2-hydroxyethoxy)methyluracils
  作者：Nitya G. Kundu、Jyan S. Mahanty、C.Paul Spears

  DOI：10.1016/s0960-894x(96)00256-9

  日期：1996.7

  5-(Acylethynyl)-1-(2-hydroxyethoxy)methyl uracils (2)-(6) were synthesised in excellent yields from 1-(2-acetoxyethoxy)methyl-5-iodouracil (7) utilising palladium-copper catalysed reactions. Compounds (2)-(5) were shown to be highly active against CCRF-CEM (IC50 0.6-1.6 mu M) and L1210/0 cells (IC50 0.7-2.2 mu M) in culture, and thus exhibit greater activity than their parent bases. Copyright (C) 1996 Elsevier Science Ltd