4-aminophenoxyethyl tetrahydro-2H-pyran-2-yl ether | 445283-42-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-aminophenoxyethyl tetrahydro-2H-pyran-2-yl ether
• 英文别名: 4-{[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]oxy}aniline；4-[2-(oxan-2-yloxy)ethoxy]aniline
• CAS: 445283-42-1
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: ZBBQZARKGJOUKD-UHFFFAOYSA-N

物化性质

• 沸点：
  406.6±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-aminophenoxyethyl tetrahydro-2H-pyran-2-yl ether 在 吡啶 、 甲醇 、 copper diacetate 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 92.0h， 生成 4-(phenylamino)phenoxyethyl 4-toluenesulfonate
  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
• 作为产物：
  描述：

  2-(2-溴乙氧基)四氢吡喃 在 5percentPd/C 氢氧化钾 、 氢气 作用下， 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 20.08h， 生成 4-aminophenoxyethyl tetrahydro-2H-pyran-2-yl ether
  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

文献信息

• [EN] 1, 2, 3-TRIAZOLE DERIVATIVES FOR USE AS STEAROYL-COA DESATURASE INHIBITORS<br/>[FR] DÉRIVÉS DE 1,2,3-TRIAZOLE DESTINÉS À ÊTRE UTILISÉS COMME INHIBITEURS DE LA STÉAROYL-COA DÉSATURASE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009060053A1

  公开（公告）日：2009-05-14

  The present invention relates to substituted triazole compounds of the formula (I) and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.

  本发明涉及公式（I）的取代三唑化合物及其药学上可接受的盐，含有它们的药物组合物以及它们在医学上的应用。具体而言，该发明涉及用于调节SCD活性的化合物。
• COMPOUNDS
  申请人：GlaxoSmithKline LLC

  公开号：US20130281499A1

  公开（公告）日：2013-10-24

  The present invention relates to substituted triazole compounds of the formula (I): and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.

  本发明涉及公式（I）的取代三唑化合物及其药学上可接受的盐，含有它们的制药组合物以及它们在医学上的应用。具体而言，本发明涉及用于调节SCD活性的化合物。
• 1,2,3-triazole derivatives for use as stearoyl-CoA desaturase inhibitors
  申请人：Bouillot Anne Marie Jeanne

  公开号：US08486977B2

  公开（公告）日：2013-07-16

  The present invention relates to substituted triazole compounds of the formula (I): and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.

  本发明涉及式(I)的取代三唑化合物及其药学上可接受的盐，包括含有它们的药物组合物和它们在医学上的应用。特别地，本发明涉及用于调节SCD活性的化合物。
• Compounds
  申请人：GlaxoSmithKline LLC

  公开号：US09051281B2

  公开（公告）日：2015-06-09

  The present invention relates to substituted triazole compounds of the formula (I): and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.

  本发明涉及式(I)的取代三唑化合物及其药学上可接受的盐，以及含有它们的制药组合物和它们在医学上的应用。特别地，本发明涉及用于调节SCD活性的化合物。
• 1,2,3-TRIAZOLE DERIVATIVES FOR USE AS STEAROYL-COA DESATURASE INHIBITORS
  申请人：Bouillot Anne Marie Jeanne

  公开号：US20100297054A1

  公开（公告）日：2010-11-25

  The present invention relates to substituted triazole compounds of the formula (I): and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.

  本发明涉及式(I)的取代三唑化合物及其药学上可接受的盐，含有它们的制药组合物以及它们在医药上的应用。特别地，本发明涉及用于调节SCD活性的化合物。