2,4-diamino-5-(3-hydroxy-4-methoxybenzyl)-pyrimidine | 83166-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,4-diamino-5-(3-hydroxy-4-methoxybenzyl)-pyrimidine
• 英文别名: 5-[(2,4-Diaminopyrimidin-5-yl)methyl]-2-methoxyphenol
• CAS: 83166-76-1
• 化学式: C₁₂H₁₄N₄O₂
• 分子量: 246.269
• InChiKey: GDSADCTVCUIMDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4-diamino-5-(3-hydroxy-4-methoxybenzyl)-pyrimidine 在 Raney Ni (W₂) 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙二醇甲醚 为溶剂， 25.0~50.0 ℃ 、500.0 kPa 条件下， 反应 1.33h， 生成 5-{3-[4-(4-Amino-benzenesulfonyl)-benzyloxy]-4-methoxy-benzyl}-pyrimidine-2,4-diamine
  参考文献：
  名称：

  Synthesis of new 2,4-diamino-5-benzylpyrimidines active against various bacterial species

  摘要：

  New inhibitors of mycobacterial dihydrofolate reductase (DHFR) have been developed. These compounds show high inhibitory activities against Gram-negative and mycobacterial DHFR exceeding that for the commercially available DHFR blockers. Amongst these compounds K-130 shows a 100-fold lower MIC against M lufu than the most active derivatives known so far (TMP, BDP). Mycobacterium lufu was used as a model for the non cultivable strain M leprae. K-130 is also very active against other mycobacterial strains. Besides the higher affinity to the isolated enzyme, the increase in lipophilicity favours permeation of the mycobacterial cell wall and is responsible for the high inhibitory power of K-130 against mycobacteria. The lower activity against Gram-negative bacteria (E coli), despite high affinity to the enzyme, is explained by the hydrophilic nature of the outer score of the cell-wall components.

  DOI：

  10.1016/0223-5234(92)90007-n
• 作为产物：
  描述：

  2,4-diamino-5-(3-benzyloxy-4-methoxybenzyl)-pyrimidine 、 甲烷 、 钯 在 盐酸 、 氨 作用下， 以 ethyleneglycol monomethylether 、 水 为溶剂， 生成 2,4-diamino-5-(3-hydroxy-4-methoxybenzyl)-pyrimidine
  参考文献：
  名称：

  Substituted 2,4-diamino-5-benzylpyrimidines, their preparation and their

  摘要：

  描述了新型替代的2,4-二氨基-5-苄基嘧啶类化合物。这些新型物质具有抗微生物活性，特别适用于抑制分枝杆菌的生长。与抑制剂如二氨基二苯砜、环替代的4-氨基二苯砜或环和/或氮替代的二氨基二苯砜结合，它们具有明显的协同作用。

  公开号：

  US04912112A1

文献信息

• Substituierte 2,4-Diamino-5-benzylpyrimidine, deren Herstellung und deren Verwendung als Arzneimittel mit antimikrobieller Wirksamkeit
  申请人：Fatol Arzneimittel GmbH

  公开号：EP0231888B1

  公开（公告）日：1992-12-30
• US4258045A
  申请人：——

  公开号：US4258045A

  公开（公告）日：1981-03-24
• US4912112A
  申请人：——

  公开号：US4912112A

  公开（公告）日：1990-03-27
• Synthesis of new 2,4-diamino-5-benzylpyrimidines active against various bacterial species
  作者：M Kansyl、JK Seydel、M Wiese、R Haller

  DOI：10.1016/0223-5234(92)90007-n

  日期：1992.4

  New inhibitors of mycobacterial dihydrofolate reductase (DHFR) have been developed. These compounds show high inhibitory activities against Gram-negative and mycobacterial DHFR exceeding that for the commercially available DHFR blockers. Amongst these compounds K-130 shows a 100-fold lower MIC against M lufu than the most active derivatives known so far (TMP, BDP). Mycobacterium lufu was used as a model for the non cultivable strain M leprae. K-130 is also very active against other mycobacterial strains. Besides the higher affinity to the isolated enzyme, the increase in lipophilicity favours permeation of the mycobacterial cell wall and is responsible for the high inhibitory power of K-130 against mycobacteria. The lower activity against Gram-negative bacteria (E coli), despite high affinity to the enzyme, is explained by the hydrophilic nature of the outer score of the cell-wall components.
• Substituted 2,4-diamino-5-benzylpyrimidines, their preparation and their
  申请人：Saarstickstoff-Fatol GmbH Chem.-Pharm. Fabrik

  公开号：US04912112A1

  公开（公告）日：1990-03-27

  Novel substituted 2,4-diamino-5-benzyl pyrimidines are described. The novel substances have antimicrobial activity and are particularly suitable for inhibiting the growth of mycobacteria. Combined with inhibitors such as diaminodiphenylsulphones, ring-substituted 4-aminodiphenylsulphones or ring and/or nitrogen-substituted diaminodiphenylsulphones, they have a marked synergistic activity.

  描述了新型替代的2,4-二氨基-5-苄基嘧啶类化合物。这些新型物质具有抗微生物活性，特别适用于抑制分枝杆菌的生长。与抑制剂如二氨基二苯砜、环替代的4-氨基二苯砜或环和/或氮替代的二氨基二苯砜结合，它们具有明显的协同作用。