2-(2-bromophenoxy)ethyl 4-methylbenzenesulfonate | 94897-00-4

• 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: 2-(2-bromophenoxy)ethyl 4-methylbenzenesulfonate
• 英文别名: 2-(o-bromophenoxy)ethyl p-toluenesulfonate；2-bromophenoxyethyl 4-toluenesulfonate；2-(2-Bromophenoxy)ethyl tosylate
• CAS: 94897-00-4
• 化学式: C₁₅H₁₅BrO₄S
• 分子量: 371.252
• InChiKey: KNBJYGPTUKBUSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenoxy)ethyl 4-methylbenzenesulfonate 在 copper(l) iodide 、 lithium methanolate 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以85%的产率得到2,3-二氢苯并呋喃
  参考文献：
  名称：

  铜催化的未活化烷基甲苯磺酸盐和甲基磺酸盐与烷基和芳基溴化物的还原交叉偶联

  摘要：

  研究了未活化的烷基甲苯磺酸盐和甲磺酸盐与烷基和芳基溴化物的铜催化还原性交叉偶联反应。它提供了一种可行的方法，可通过易于获得的底物进行立体控制，从而高效，经济地构建芳基-烷基和烷基-烷基CC键。当以分子内方式使用时，该反应可方便地获得各种取代的碳环或杂环，例如2,3-二氢苯并呋喃和苯并色烯衍生物。

  DOI：

  10.1002/chem.201405223
• 作为产物：
  描述：

  2-bromophenoxyethyl tetrahydro-2H-pyran-2-yl ether 在 吡啶 、 甲醇 、 4-甲基苯磺酸吡啶 作用下， 反应 20.0h， 生成 2-(2-bromophenoxy)ethyl 4-methylbenzenesulfonate
  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

• Novel compounds
  申请人：——

  公开号：US20040242573A1

  公开（公告）日：2004-12-02

  The invention relates to thiophene carboxanmides of formula (I). wherein A, R 1 , R 2 , R 3 , n and X are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy. 1

  本发明涉及公式（I）的噻吩羧酰胺，其中A，R1，R2，R3，n和X如规范中定义的，以及用于其制备的工艺和中间体，含有它们的制药组合物以及它们在治疗中的使用。
• Thiophene carboxamide compounds as inhibitors of enzyme IKK-2
  申请人：AstraZeneca AB

  公开号：US07125896B2

  公开（公告）日：2006-10-24

  The invention relates to thiophene carboxanmides of formula (I), wherein A, R1, R2, R3, n and X are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明涉及公式（I）的噻吩羧酰胺，其中A，R1，R2，R3，n和X如规范中所定义，用于制备它们的过程和中间体，包含它们的制药组合物以及它们在治疗中的使用。
• Novel Compounds
  申请人：Faull Alan

  公开号：US20110152234A1

  公开（公告）日：2011-06-23

  The invention relates to thiophene carboxamides of formula (I), wherein A, R 1 , R 2 , R 3 , n and X are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.

  该发明涉及式(I)的噻吩羧酰胺，其中A、R1、R2、R3、n和X如规范中所定义，以及用于其制备的过程和中间体，含有它们的制药组合物以及它们在治疗中的使用。
• Phenyl thiophene carboxamide compounds as inhibitors of the enzyme IKK-2
  申请人：AstraZeneca AB

  公开号：US07956084B2

  公开（公告）日：2011-06-07

  The invention relates to thiophene carboxamides of formula (I), wherein A, R1, R2, R3, n and X are as defined in the specification, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明涉及式（I）的噻吩羧酰胺，其中A，R1，R2，R3，n和X如规范所定义，以及用于其制备的过程和中间体，包含它们的制药组合物以及它们在治疗中的使用。
• Raguse, Burkhard; Ridley, Damon D., Australian Journal of Chemistry, 1984, vol. 37, # 10, p. 2059 - 2071
  作者：Raguse, Burkhard、Ridley, Damon D.

  DOI：——

  日期：——