2-benzyl-N-(3-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-sulfonamide | 1215657-73-0

• 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-benzyl-N-(3-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-sulfonamide
• 英文别名: 2-benzyl-N-(3-fluorophenyl)-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-sulfonamide
• CAS: 1215657-73-0
• 化学式: C₂₄H₂₂FN₃O₂S
• 分子量: 435.522
• InChiKey: KLXAHKWEYNGGPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzyl-N-(3-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-sulfonamide 在 盐酸 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 生成 2-benzyl-N-(3-fluorophenyl)-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-sulfonamide;hydrochloride
  参考文献：
  名称：

  SUBSTITUTED 8-SULFONYL-2,3,4,5-TETRAHYDRO-1H-GAMMA-CARBOLINES, LIGANDS AND PHARMACEUTICAL COMPOSITION; METHOD FOR THE PRODUCTION AND USE OF SAME

  摘要：

  该发明涉及一种新型的取代的8-磺酰基-2,3,4,5-四氢-1H-γ-咔啉的化合物，其一般式为1，以及它们的药用盐——配体，同时对α-肾上腺素受体、多巴胺受体、组胺受体、咪唑啉受体、西格玛受体、去甲肾上腺素受体、5-羟色胺受体表现出生物活性的配体，以及作为活性成分的新型配体组成的药物组合物，用于治疗中枢神经系统疾病和病症的新型药物。在一般式1中，R1代表从氢、可选取代的C1-C3烷基或C1-C4烷氧羰基中选择的取代基；R2代表从氢、可选取代的C1-C3烷基、可选取代的C2-C3烯基或取代的磺酰基中选择的环系统取代基；R3代表可选取代的芳基或取代的氨基团。

  公开号：

  US20120071493A1
• 作为产物：
  描述：

  3-氟苯胺 、 2-Benzyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-sulfonyl chloride 在 吡啶 作用下， 反应 1.0h， 以76%的产率得到2-benzyl-N-(3-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-sulfonamide
  参考文献：
  名称：

  8-Sulfonyl-substituted tetrahydro-1 H -pyrido[4,3- b ]indoles as 5-HT 6 receptor antagonists

  摘要：

  A series of novel 8-sulfonyl-substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles (THPI) has been synthesized and their ability to interact with 5-HT6 receptors evaluated in cell-based and radioligand binding assays. Amongst evaluated THPIs, compounds 9 center dot HCl and 20 center dot HCl have been identified as the most potent 5-HT6 receptor antagonists with K-i values equal to 2.1 nM and 5.7 nM and IC50 values (functional assay) equal to 15 nM and 78 nM, respectively. Affinities of these two compounds for several serotonin receptors in the competitive radioligand binding assays as well as their specificity profiles against a panel of therapeutic targets have been determined. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.035

文献信息

• [EN] SUBSTITUTED 8-SULFONYL-2,3,4,5-TETRAHYDRO-1H-GAMMA-CARBOLINES, LIGANDS AND PHARMACEUTICAL COMPOSITION; METHOD FOR THE PRODUCTION AND USE OF SAME<br/>[FR] CARBOLINES 8-SULFONYL-2,3,4,5-TÉTRAHYDRO-1H-GAMMA SUBSTITUÉS, LIGANS, COMPOSITION PHARMACEUTIQUE, PROCÉDÉ DE FABRICATION ET D'UTILISATION
  申请人：IVASHCHENKO ANDREY ALEXANDROVICH

  公开号：WO2010134846A1

  公开（公告）日：2010-11-25

  Данное изобретение относится к новым замещенным 8-cyльфoнил-2,3,4,5- тетрагидро-1H- γ-карболинам общей формулы 1 и их фармацевтически приемлемым солям - лигандам, обладающим биологической активностью одновременно в отношении альфа-адреноцепторов, допаминовых рецепторов, гистаминовых рецепторов, имидазолиновых рецепторов, сигма рецепторов, норепинефриневых рецепторов, серотониновых рецепторов, к активным компонентам, фармацевтическим композициям, содержащим в качестве активного компонента новые лиганды, к новым лекарственным средствам, применяемым для лечения болезней и состояний центральной нервной системы. В общей формуле 1 R1 представляет собой заместитель, выбранный из водорода, необязательно замещенного C1-C3 алкила или C1-C4 алкилоксикарбонила; R2 представляет собой заместитель циклической системы, в том числе атом водорода, необязательно замещенный C1-C3 алкил, необязательно замещенный C2-C3 алкенил или замещенный сульфонил; R3 представляет собой необязательно замещенный арил или замещенную аминогруппу.
• SUBSTITUTED 8-SULFONYL-2,3,4,5-TETRAHYDRO-1H-GAMMA-CARBOLINES, LIGANDS AND PHARMACEUTICAL COMPOSITION; METHOD FOR THE PRODUCTION AND USE OF SAME
  申请人：Ivashchenko Andrey Alexandrovich

  公开号：US20120071493A1

  公开（公告）日：2012-03-22

  The invention relates to novel substituted 8-sulfonyl-2,3,4,5-tetrahydro-1H-γ-carbolines of the general formula 1 and their pharmaceutically acceptable salt—ligands exhibiting biological activity simultaneously towards alpha-adrenoceptors, dopamine receptors, histamine receptors, imidazoline receptors, sigma receptors, norepinefrine receptors, serotonin receptors, to active components, pharmaceutical compositions, comprising as an active component novel ligands, to novel medicaments intended for treatment of conditions and diseases of central nervous system. In the general formula 1 R 1 represents a substituent selected from hydrogen, optionally substituted C 1 -C 3 alkyl or C 1 -C 4 alkyloxycarbonyl; R 2 represents a cyclic system substituent selected from hydrogen, optionally substituted C 1 -C 3 alkyl, optionally substituted C 2 -C 3 alkenyl or substituted sulfonyl; R 3 represents optionally substituted aryl or substituted amino group.

  该发明涉及一种新型的取代的8-磺酰基-2,3,4,5-四氢-1H-γ-咔啉的化合物，其一般式为1，以及它们的药用盐——配体，同时对α-肾上腺素受体、多巴胺受体、组胺受体、咪唑啉受体、西格玛受体、去甲肾上腺素受体、5-羟色胺受体表现出生物活性的配体，以及作为活性成分的新型配体组成的药物组合物，用于治疗中枢神经系统疾病和病症的新型药物。在一般式1中，R1代表从氢、可选取代的C1-C3烷基或C1-C4烷氧羰基中选择的取代基；R2代表从氢、可选取代的C1-C3烷基、可选取代的C2-C3烯基或取代的磺酰基中选择的环系统取代基；R3代表可选取代的芳基或取代的氨基团。
• 8-Sulfonyl-substituted tetrahydro-1 H -pyrido[4,3- b ]indoles as 5-HT 6 receptor antagonists
  作者：Alexandre V. Ivachtchenko、Oleg D. Mitkin、Sergey E. Tkachenko、Ilya M. Okun、Volodymyr M. Kysil

  DOI：10.1016/j.ejmech.2009.10.035

  日期：2010.2

  A series of novel 8-sulfonyl-substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles (THPI) has been synthesized and their ability to interact with 5-HT6 receptors evaluated in cell-based and radioligand binding assays. Amongst evaluated THPIs, compounds 9 center dot HCl and 20 center dot HCl have been identified as the most potent 5-HT6 receptor antagonists with K-i values equal to 2.1 nM and 5.7 nM and IC50 values (functional assay) equal to 15 nM and 78 nM, respectively. Affinities of these two compounds for several serotonin receptors in the competitive radioligand binding assays as well as their specificity profiles against a panel of therapeutic targets have been determined. (C) 2009 Elsevier Masson SAS. All rights reserved.