5-[3-(o-anisyl)-3-hydroxyprop-1-ynyl]-2,4-dimethoxypyrimidine | 249509-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[3-(o-anisyl)-3-hydroxyprop-1-ynyl]-2,4-dimethoxypyrimidine
• 英文别名: 3-(2,4-Dimethoxypyrimidin-5-yl)-1-(2-methoxyphenyl)prop-2-yn-1-ol
• CAS: 249509-31-7
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: GJFZPSPUXZXRIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[3-(o-anisyl)-3-hydroxyprop-1-ynyl]-2,4-dimethoxypyrimidine 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到5-(o-anisoylethynyl)-2,4-dimethoxypyrimidine
  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-甲氧基苯基)-2-丙炔-1-醇 、 2,4-二甲氧基-5-碘嘧啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 作用下， 以 三乙胺 为溶剂， 以89%的产率得到5-[3-(o-anisyl)-3-hydroxyprop-1-ynyl]-2,4-dimethoxypyrimidine
  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.