2,4-dimethoxy-5-(m-toluoylethynyl)pyrimidine | 249509-34-0

• 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: 2,4-dimethoxy-5-(m-toluoylethynyl)pyrimidine
• 英文别名: 3-(2,4-Dimethoxypyrimidin-5-yl)-1-(3-methylphenyl)prop-2-yn-1-one
• CAS: 249509-34-0
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: FLHPAUXVNJRRKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  61.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-dimethoxy-5-(m-toluoylethynyl)pyrimidine 在 盐酸 作用下， 以60%的产率得到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-(间甲基苯基)-2-丙炔-1-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide manganese(IV) oxide 作用下， 以 二氯甲烷 、 三乙胺 为溶剂， 生成 2,4-dimethoxy-5-(m-toluoylethynyl)pyrimidine
  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

• 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]
  作者：Nitya G. Kundu、Jyan S. Mahanty、Chinmay Chowdhury、Swapan K. Dasgupta、Biswajit Das、Colin Paul Spears、Jan Balzarini、Erik De Clercq

  DOI：10.1016/s0223-5234(99)80088-9

  日期：1999.5

  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.