5-(4-Methoxy-3-{2-[4-(4-nitro-benzenesulfonyl)-phenylamino]-ethoxy}-benzyl)-pyrimidine-2,4-diamine | 111452-85-8

• 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-(4-Methoxy-3-{2-[4-(4-nitro-benzenesulfonyl)-phenylamino]-ethoxy}-benzyl)-pyrimidine-2,4-diamine
• CAS: 111452-85-8
• 化学式: C₂₆H₂₆N₆O₆S
• 分子量: 550.595
• InChiKey: MNFAGLUFKGCLRP-UHFFFAOYSA-N

物化性质

• 沸点：
  862.3±75.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  185.59
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5-(4-Methoxy-3-{2-[4-(4-nitro-benzenesulfonyl)-phenylamino]-ethoxy}-benzyl)-pyrimidine-2,4-diamine 在 Raney Ni (W₂) 氢气 作用下， 以 甲醇 、 乙二醇甲醚 为溶剂， 50.0 ℃ 、500.0 kPa 条件下， 反应 1.33h， 以63%的产率得到5-(3-{2-[4-(4-Amino-benzenesulfonyl)-phenylamino]-ethoxy}-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：

  N-(2-bromo-ethyl)-4-(4-nitro-benzenesulfonyl)-aniline 、 2,4-diamino-5-(3-hydroxy-4-methoxybenzyl)-pyrimidine 在 sodium methylate 作用下， 以 乙二醇甲醚 为溶剂， 以21%的产率得到5-(4-Methoxy-3-{2-[4-(4-nitro-benzenesulfonyl)-phenylamino]-ethoxy}-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