2,4-Diamino-5-<3-aethoxy-benzyl>-pyrimidin | 93258-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-Diamino-5-<3-aethoxy-benzyl>-pyrimidin
• 英文别名: 5-(3-ethoxy-benzyl)-pyrimidine-2,4-diamine；5-[(3-ethoxyphenyl)methyl]pyrimidine-2,4-diamine
• CAS: 93258-10-7
• 化学式: C₁₃H₁₆N₄O
• 分子量: 244.296
• InChiKey: KTYSFHHOATVLLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(tetrahydro-2H-2-pyranyloxy)benzaldehyde 在 盐酸 、 氢氧化钾 、 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 51.58h， 生成 2,4-Diamino-5-<3-aethoxy-benzyl>-pyrimidin
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Inhibitors of Trypanosomal and Leishmanial Dihydrofolate Reductase

  摘要：

  This paper concerns the design, synthesis, and evaluation of inhibitors of leishmanial and trypanosomal dihydrofolate reductase. Initially study was made of the structures of the leishmanial and human enzyme active sites to see if there were significant differences which could be exploited for selective drug design. Then a series of compounds were synthesized based on 5-benzyl-2,4-diaminopyrimidines. These compounds were assayed against the protozoan and human enzymes and showed selectivity for the protozoan enzymes. The structural data was then used to rationalize the enzyme assay data. Compounds were also tested against the clinically relevant forms of the intact parasite. Activity was seen against the trypanosomes for a number of compounds. The compounds were in general less active against Leishmania. This latter result may be due to uptake problems. Two of the compounds also showed some in vivo activity in a model of African trypanosomiasis.

  DOI：

  10.1021/jm981130+

文献信息

• Design, Synthesis, and Evaluation of Inhibitors of Trypanosomal and Leishmanial Dihydrofolate Reductase
  作者：Shafinaz F. Chowdhury、Victor Bernier Villamor、Ramon Hurtado Guerrero、Isabel Leal、Reto Brun、Simon L. Croft、Jonathan M. Goodman、Louis Maes、Luis M. Ruiz-Perez、Dolores Gonzalez Pacanowska、Ian H. Gilbert

  DOI：10.1021/jm981130+

  日期：1999.10.1

  This paper concerns the design, synthesis, and evaluation of inhibitors of leishmanial and trypanosomal dihydrofolate reductase. Initially study was made of the structures of the leishmanial and human enzyme active sites to see if there were significant differences which could be exploited for selective drug design. Then a series of compounds were synthesized based on 5-benzyl-2,4-diaminopyrimidines. These compounds were assayed against the protozoan and human enzymes and showed selectivity for the protozoan enzymes. The structural data was then used to rationalize the enzyme assay data. Compounds were also tested against the clinically relevant forms of the intact parasite. Activity was seen against the trypanosomes for a number of compounds. The compounds were in general less active against Leishmania. This latter result may be due to uptake problems. Two of the compounds also showed some in vivo activity in a model of African trypanosomiasis.