[3-(2-aminoethyl)-1H-indol-5-yl] thiophene-2-sulfonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [3-(2-aminoethyl)-1H-indol-5-yl] thiophene-2-sulfonate
• 化学式: C₁₄H₁₄N₂O₃S₂
• 分子量: 322.409
• InChiKey: ZJGJPYDXABTAQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2-(5-hydroxy-1H-indol-3-yl)ethyl)isoindoline-1,3-dione 在 sodium hydroxide 、 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 [3-(2-aminoethyl)-1H-indol-5-yl] thiophene-2-sulfonate
  参考文献：
  名称：

  5-(Sulfonyl)oxy-tryptamines and ethylamino side chain restricted derivatives. Structure–affinity relationships for h5-HT 1B and h5-HT 1D receptors

  摘要：

  A number of sulfonic acid ester derivatives of serotonin (5-hydroxytryptamine; 5-HT; 1) were prepared and their affinities are compared to that of the reference compound 5-[[(trifluoromethyl)sulfonyl]oxy]-tryptamine (8b). The structure-affinity relationship (SAFIR) is discussed in terms of in vitro binding for cloned human h5-HT1A, h5-HT1B and h5-HT1D receptors. All tryptamine derivatives exhibited the best affinities for h5-HT1D receptors but still, these were comparatively lower than that of compound 8b. 5-Tosylated tryptamine 11b (K-i = 6 nM) and the sulfamate derivatives 13b and 14b (K-i = 7 and 11 nM, respectively) were found to have the highest affinities for the h5-HT1D receptor. Other tryptamine derivatives displayed moderate binding for h5-HT1A and h5-HT1B receptors, along with Ki values ranging from 14-20 nM for the h5-HT1D sites. In addition, the syntheses of two alkylamino side chain restricted derivatives are described. 3-Amino-6-[[(trifluoromethyl)sulfonyl]oxy]-1,2,3,4-tetrahydrocarbazole 21, as well as 4-[5-[[(trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]piperidines 24 and 25, induced a shift in selectivity in favor of the h5-HT1B receptor. The relatively longer distance between the basic amine and a hydrogen-bond accepting oxygen in 21, 24 and 25 as compared to the non-restricted tryptamines, is likely responsible for this observation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00079-0

文献信息

• 5-(Sulfonyl)oxy-tryptamines and ethylamino side chain restricted derivatives. Structure–affinity relationships for h5-HT 1B and h5-HT 1D receptors
  作者：Tjeerd Barf、Håkan Wikström、Petrus J. Pauwels、Christiane Palmier、Stephanie Tardif、Max Lundmark、Staffan Sundell

  DOI：10.1016/s0968-0896(98)00079-0

  日期：1998.9

  A number of sulfonic acid ester derivatives of serotonin (5-hydroxytryptamine; 5-HT; 1) were prepared and their affinities are compared to that of the reference compound 5-[[(trifluoromethyl)sulfonyl]oxy]-tryptamine (8b). The structure-affinity relationship (SAFIR) is discussed in terms of in vitro binding for cloned human h5-HT1A, h5-HT1B and h5-HT1D receptors. All tryptamine derivatives exhibited the best affinities for h5-HT1D receptors but still, these were comparatively lower than that of compound 8b. 5-Tosylated tryptamine 11b (K-i = 6 nM) and the sulfamate derivatives 13b and 14b (K-i = 7 and 11 nM, respectively) were found to have the highest affinities for the h5-HT1D receptor. Other tryptamine derivatives displayed moderate binding for h5-HT1A and h5-HT1B receptors, along with Ki values ranging from 14-20 nM for the h5-HT1D sites. In addition, the syntheses of two alkylamino side chain restricted derivatives are described. 3-Amino-6-[[(trifluoromethyl)sulfonyl]oxy]-1,2,3,4-tetrahydrocarbazole 21, as well as 4-[5-[[(trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]piperidines 24 and 25, induced a shift in selectivity in favor of the h5-HT1B receptor. The relatively longer distance between the basic amine and a hydrogen-bond accepting oxygen in 21, 24 and 25 as compared to the non-restricted tryptamines, is likely responsible for this observation. (C) 1998 Elsevier Science Ltd. All rights reserved.