5-(3,5-di-tert-butyl-4-hydroxybenzyl)uracil | 73943-43-8

• 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: 5-(3,5-di-tert-butyl-4-hydroxybenzyl)uracil
• 英文别名: 5-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1H-pyrimidine-2,4-dione
• CAS: 73943-43-8
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: AYGUVOUABVOICG-UHFFFAOYSA-N

物化性质

• 熔点：
  326-329 °C (decomp)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(3,5-di-tert-butyl-4-hydroxybenzyl)uracil 在 三氯氧磷 作用下， 反应 2.5h， 以70.9%的产率得到2,4-dichloro-5-(3,5-di-tert-butyl-4-hydroxybenzyl)pyrimidine
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 9. Lipophilic trimethoprim analogs as antigonococcal agents

  摘要：

  Lipophilic analogues of trimethoprim (1) bearing 3,5-dialkyl-4-hydroxy substituents in the benzene ring are much more active in vitro against Neisseria gonorrhoeae than is 1. The 3,5-diisopropyl-4-hydroxy derivative (2) was selected as a candidate for clinical evaluation as an antigonococcal agent, and as part of the preliminary evaluation it was submitted to extended pharmacokinetic and metabolism studies in dogs. Although the compound was not extensively conjugated by metabolic enzymes, one of the methyl groups was metabolized to produce a 3-isopropyl-4-hydroxy-5-(alpha-carboxyethyl)benzyl derivative (43), which was rapidly excreted. Related analogues were likewise extensively metabolized.

  DOI：

  10.1021/jm00396a018
• 作为产物：
  描述：

  尿嘧啶 、 2,6-二叔丁基对(二甲氨甲基)苯酚 在 sodium methylate 作用下， 以 乙二醇 为溶剂， 反应 6.0h， 以78.7%的产率得到5-(3,5-di-tert-butyl-4-hydroxybenzyl)uracil
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 9. Lipophilic trimethoprim analogs as antigonococcal agents

  摘要：

  Lipophilic analogues of trimethoprim (1) bearing 3,5-dialkyl-4-hydroxy substituents in the benzene ring are much more active in vitro against Neisseria gonorrhoeae than is 1. The 3,5-diisopropyl-4-hydroxy derivative (2) was selected as a candidate for clinical evaluation as an antigonococcal agent, and as part of the preliminary evaluation it was submitted to extended pharmacokinetic and metabolism studies in dogs. Although the compound was not extensively conjugated by metabolic enzymes, one of the methyl groups was metabolized to produce a 3-isopropyl-4-hydroxy-5-(alpha-carboxyethyl)benzyl derivative (43), which was rapidly excreted. Related analogues were likewise extensively metabolized.

  DOI：

  10.1021/jm00396a018

文献信息

• 2,4-Diamino-5-benzylpyrimidines, especially for the treatment of microbial infections, pharmaceutical compositions containing these compounds and processes for preparing these compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0006987A1

  公开（公告）日：1980-01-23

  Pharmaceutical compositions containing 2,4-diamino-5-(3. 5-dialkyl-4-hydroxybenzyl) pyrimidines wherein the alkyl groups contain from 2 to 4 carbon atoms are useful in the treatment of bacterial infections. The first medical use of such compounds, novel chemical compounds wherein the alkyl groups are propyl or butyl, except the di-i-propyl compound, a process for preparing the novel compounds and chemical intermediates used in their preparation are also disclosed.

  含有 2,4-二氨基-5-(3. 5-二烷基-4-羟基苄基)嘧啶（其中烷基含有 2 至 4 个碳原子）的药物组合物可用于治疗细菌感染。此外，还公开了此类化合物的第一种医学用途、烷基为丙基或丁基的新型化合物（二丙基化合物除外）、制备新型化合物的工艺以及用于制备这些化合物的化学中间体。
• ROTH, B.;BACCANARI, D. P.;SIGEL, C. W.;HUBBELL, J. P.;EADDY, J.;KAO, J. C+, J. MED. CHEM., 31,(1988) N 1, 122-129
  作者：ROTH, B.、BACCANARI, D. P.、SIGEL, C. W.、HUBBELL, J. P.、EADDY, J.、KAO, J. C+

  DOI：——

  日期：——
• 2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 9. Lipophilic trimethoprim analogs as antigonococcal agents
  作者：B. Roth、D. P. Baccanari、C. W. Sigel、J. P. Hubbell、J. Eaddy、J. C. Kao、M. E. Grace、B. S. Rauckman

  DOI：10.1021/jm00396a018

  日期：1988.1

  Lipophilic analogues of trimethoprim (1) bearing 3,5-dialkyl-4-hydroxy substituents in the benzene ring are much more active in vitro against Neisseria gonorrhoeae than is 1. The 3,5-diisopropyl-4-hydroxy derivative (2) was selected as a candidate for clinical evaluation as an antigonococcal agent, and as part of the preliminary evaluation it was submitted to extended pharmacokinetic and metabolism studies in dogs. Although the compound was not extensively conjugated by metabolic enzymes, one of the methyl groups was metabolized to produce a 3-isopropyl-4-hydroxy-5-(alpha-carboxyethyl)benzyl derivative (43), which was rapidly excreted. Related analogues were likewise extensively metabolized.