phenyl-{4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-[2(tetrahydropyran-2-yloxy)ethylamine]

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: phenyl-{4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-[2(tetrahydropyran-2-yloxy)ethylamine]
• 英文别名: 4-[2-(oxan-2-yloxy)ethoxy]-N-[2-(oxan-2-yloxy)ethyl]-N-phenylaniline
• 化学式: C₂₆H₃₅NO₅
• 分子量: 441.568
• InChiKey: UHTZDQMQRWGEAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-硝基苯基乙酸酯 在 5percent Pd/C 吡啶 、 氢氧化钾 、 copper diacetate 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 96.08h， 生成 phenyl-{4-[2-(tetrahydropyran-2-yloxy)ethoxy]phenyl}-[2(tetrahydropyran-2-yloxy)ethylamine]
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Aryloxyethyl Thiocyanate Derivatives against Trypanosoma cruzi

  摘要：

  As a continuation of our project aimed at the search for new and safe chemotherapeutic and chemoprophylactic agents against American trypanosomiasis (Chagas' disease), several drugs structurally related to 4-phenoxyphenoxyethyl thiocyanate (4) were designed, synthesized, and evaluated as antiproliferative agents against the parasite responsible for this disease, the hemoflagellated protozoan Trypanosoma cruzi. This thiocyanate derivative was previously shown to be an effective and potent agent against T. cruzi proliferation. Several drugs possessing thiocyanate groups proved to be effective growth inhibitors of T. cruzi growth. Among the designed compounds, it is important to point out the extremely potent activity shown by 11, 23, 38, 53, 90, 99, and 117 against the epimastigote forms of the parasite. All of them exhibited IC50 values in the low micromolar range, and these values were comparable with those presented by our lead drug 4 and ketokonazole, a well-known antiparasitic agent. The activity displayed by the nitrogen-containing derivative 90 was very promising with IC50 values of 3.3 muM. Several other thiocyanate derivatives also proved to be very potent inhibitors of the multiplication of T. cruzi epimastigotes, such as compounds 28, 33, 43, 48, 56, 61, 66, 71, 76, and 124. Compound 43 resulted in being a promising drug because it was also very effective against amastigotes, the clinically more relevant form of the parasite. This compound was Mold more potent than 4, while 11 showed nearly the same activity as our lead drug against intracellular T. cruzi. It was very surprising that the experimental juvenoid 124, although fairly devoid of activity against epimastigotes, was very effective against intracellular amastigotes growing in myoblasts. The rest of the designed compounds showed a broad degree of inhibitory action, from moderately active drugs to drugs almost devoid of antiparasitic activity. Compound 43 is an interesting example of an effective antichagasic agent that presents excellent prospectives not only as a lead drug but also to be used for further in vivo studies.

  DOI：

  10.1021/jm0201518