2,4-diamino-5-(3,5-diallyl-4-hydroxybenzyl)pyrimidine | 121962-55-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2,4-diamino-5-(3,5-diallyl-4-hydroxybenzyl)pyrimidine
• 英文别名: 4-[(2,4-Diaminopyrimidin-5-yl)methyl]-2,6-bis(prop-2-enyl)phenol
• CAS: 121962-55-8
• 化学式: C₁₇H₂₀N₄O
• 分子量: 296.372
• InChiKey: FWDNTBGILYDZAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  98
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-diamino-5-(3,5-diallyl-4-hydroxybenzyl)pyrimidine 在 sodium hydroxide 、 potassium tert-butylate 、 苄基三丁基氯化铵 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 1.25h， 生成 2,4-diamino-5-<3,5-bis(1-propenyl)-4-methoxybenzyl>pyrimidine
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 13. Some alkenyl derivatives with high in vitro activity against anaerobic organisms

  摘要：

  A series of 2,4-diamino-5-(3,5-dialkenyl-4-methoxy- or -4-hydroxybenzyl)pyrimidines was prepared from [(allyloxy)benzyl]pyrimidines by Claisen rearrangements, and the resulting allyl phenols were further modified by methylation and rearrangement to 1-propenyl analogues. Analogous 3,4-dimethoxy-5-alkenyl derivatives were prepared by similar techniques. High in vitro antibacterial activity was obtained against certain anaerobic organisms, such as Bacteroides species and Fusobacterium, which was equal to or better than the control, metronidazole, in several cases. The profile was similar against Neisseria gonorrhoeae and Staphylococcus aureus. The 3,5-bis(1-propenyl)-4-methoxy derivative 8 was 1 order of magnitude more active against Escherichia coli dihydrofolate reductase than its saturated counterpart, and it was also more active than trimethoprim, 1. However, it was considerably less active in vitro against the Gram-negative organisms. The 3,4-dimethoxy-5-alkenyl, -5-alkyl, and -5-alkoxy analogues had very high broad-spectrum antibacterial activity. However, pharmacokinetic studies of four of the compounds in dogs and rats and in vivo studies with an abdominal sepsis model in rats showed no advantages over trimethoprim.

  DOI：

  10.1021/jm00128a043
• 作为产物：
  描述：

  2,4-diamino-5-[4-(allyloxy)benzyl]pyrimidine 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.5h， 生成 2,4-diamino-5-(3,5-diallyl-4-hydroxybenzyl)pyrimidine
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 13. Some alkenyl derivatives with high in vitro activity against anaerobic organisms

  摘要：

  A series of 2,4-diamino-5-(3,5-dialkenyl-4-methoxy- or -4-hydroxybenzyl)pyrimidines was prepared from [(allyloxy)benzyl]pyrimidines by Claisen rearrangements, and the resulting allyl phenols were further modified by methylation and rearrangement to 1-propenyl analogues. Analogous 3,4-dimethoxy-5-alkenyl derivatives were prepared by similar techniques. High in vitro antibacterial activity was obtained against certain anaerobic organisms, such as Bacteroides species and Fusobacterium, which was equal to or better than the control, metronidazole, in several cases. The profile was similar against Neisseria gonorrhoeae and Staphylococcus aureus. The 3,5-bis(1-propenyl)-4-methoxy derivative 8 was 1 order of magnitude more active against Escherichia coli dihydrofolate reductase than its saturated counterpart, and it was also more active than trimethoprim, 1. However, it was considerably less active in vitro against the Gram-negative organisms. The 3,4-dimethoxy-5-alkenyl, -5-alkyl, and -5-alkoxy analogues had very high broad-spectrum antibacterial activity. However, pharmacokinetic studies of four of the compounds in dogs and rats and in vivo studies with an abdominal sepsis model in rats showed no advantages over trimethoprim.

  DOI：

  10.1021/jm00128a043

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, BARBARA;TIDWELL, MARY Y.;FERONE, ROBERT;BACCANAR, DAVID P.;SIGEL, C+, J. MED. CHEM., 32,(1989) N, C. 1949-1958
  作者：ROTH, BARBARA、TIDWELL, MARY Y.、FERONE, ROBERT、BACCANAR, DAVID P.、SIGEL, C+

  DOI：——

  日期：——
• 2,4-Diamino-5-benzylpyrimidines as antibacterial agents. 13. Some alkenyl derivatives with high in vitro activity against anaerobic organisms
  作者：Barbara Roth、Mary Y. Tidwell、Robert Ferone、David P. Baccanari、Carl W. Sigel、Diane DeAngelis、Lynn P. Elwell

  DOI：10.1021/jm00128a043

  日期：1989.8

  A series of 2,4-diamino-5-(3,5-dialkenyl-4-methoxy- or -4-hydroxybenzyl)pyrimidines was prepared from [(allyloxy)benzyl]pyrimidines by Claisen rearrangements, and the resulting allyl phenols were further modified by methylation and rearrangement to 1-propenyl analogues. Analogous 3,4-dimethoxy-5-alkenyl derivatives were prepared by similar techniques. High in vitro antibacterial activity was obtained against certain anaerobic organisms, such as Bacteroides species and Fusobacterium, which was equal to or better than the control, metronidazole, in several cases. The profile was similar against Neisseria gonorrhoeae and Staphylococcus aureus. The 3,5-bis(1-propenyl)-4-methoxy derivative 8 was 1 order of magnitude more active against Escherichia coli dihydrofolate reductase than its saturated counterpart, and it was also more active than trimethoprim, 1. However, it was considerably less active in vitro against the Gram-negative organisms. The 3,4-dimethoxy-5-alkenyl, -5-alkyl, and -5-alkoxy analogues had very high broad-spectrum antibacterial activity. However, pharmacokinetic studies of four of the compounds in dogs and rats and in vivo studies with an abdominal sepsis model in rats showed no advantages over trimethoprim.