7-(N,N-pentane-1,5-diylcarboxamido)indole | 1056002-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 7-(N,N-pentane-1,5-diylcarboxamido)indole
• 英文别名: Piperidino(1H-indole-7-yl) ketone；1H-indol-7-yl(piperidin-1-yl)methanone
• CAS: 1056002-16-4
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: NGEFVWHYXNYTFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 7-(N,N-pentane-1,5-diylcarboxamido)indole 、 1-环丁基哌嗪 在 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 生成 [3-(4-cyclobutyl-piperazin-1-ylmethyl)-1H-indol-7-yl]-piperidin-1-yl-methanone
  参考文献：
  名称：

  Indole- and benzothiophene-based histamine H3 antagonists

  摘要：

  Previous research on histamine H-3 antagonists has led to the development of a pharmacophore model consisting of a central phenyl core flanked by two alkylamine groups. Recent investigation of the replacement of the central phenyl core with heteroaromatic fragments resulted in the preparation of novel 3,5-, 3,6- and 3,7-substituted indole and 3,5-substituted benzothiophene analogs that demonstrate good to excellent hH(3) affinities. Select analogs were profiled in a rat pharmacokinetic model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.103
• 作为产物：
  描述：

  哌啶 、 7-吲哚甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到7-(N,N-pentane-1,5-diylcarboxamido)indole
  参考文献：
  名称：

  Indole- and benzothiophene-based histamine H3 antagonists

  摘要：

  Previous research on histamine H-3 antagonists has led to the development of a pharmacophore model consisting of a central phenyl core flanked by two alkylamine groups. Recent investigation of the replacement of the central phenyl core with heteroaromatic fragments resulted in the preparation of novel 3,5-, 3,6- and 3,7-substituted indole and 3,5-substituted benzothiophene analogs that demonstrate good to excellent hH(3) affinities. Select analogs were profiled in a rat pharmacokinetic model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.103

文献信息

• Functionalization of indole at C-5 or C-7 via palladium-catalysed double carbonylation. A facile synthesis of indole ketocarboxamides and carboxamide dimers
  作者：Attila Takács、Diána Marosvölgyi-Haskó、Zsuzsanna Kabak-Solt、Liliana Damas、Fábio M.S. Rodrigues、Rui M.B. Carrilho、Marta Pineiro、Mariette M. Pereira、László Kollár

  DOI：10.1016/j.tet.2015.11.007

  日期：2016.1

  Palladium-catalysed aminocarbonylation of 7-iodoindole derivatives (the parent compound and 5-bromo-7-iodoindole), as well as 5-iodoindole with various primary and secondary amines, including amino acid esters and chiral diamines, was carried out. In this way, a highly selective double carbonylation reaction at the C-7 was performed resulting in the formation of the corresponding indol-7-ylglyoxylamides

  进行了钯催化的7-碘吲哚衍生物（母体化合物和5-bromo-7-碘吲哚）以及5-碘吲哚与各种伯胺和仲胺（包括氨基酸酯和手性二胺）的氨基羰基化反应。这样，当使用单胺时，在C-7上进行了高度选择性的双羰基化反应，导致形成了相应的吲哚-7-乙醛酰乙二酰亚胺。溴芳烃部分保持完好无损，因此已经以中等至高收率合成了具有实际重要性的溴取代的乙氧化乙酰胺。使用手性烷基和芳基二胺作为亲核试剂，可以在中等反应条件（10 bar，100°C）下合成新的二聚7-吲哚衍生物家族。 碘吲哚的氨基羰基化反应显示出极大不同的化学选择性，这取决于胺的碱性，而高碱性的伯胺和仲胺则可产生高达98％的化学选择性的2-酮羧酰胺，苯胺几乎导致了相应羧酰胺产物的排他性形成。
• INDOLE AND BENZOTHIOPHENE COMPOUNDS AS MODULATORS OF THE HISTAMINE H3 RECEPTOR
  申请人：Allison Brett D.

  公开号：US20110178062A1

  公开（公告）日：2011-07-21

  Certain substituted indole and benzothiophene compounds are histamine H 3 receptor modulators useful in the treatment of histamine H 3 receptor-mediated diseases.

  某些取代的吲哚和苯并噻吩化合物是组胺H3受体调节剂，可用于治疗组胺H3受体介导的疾病。
• [EN] INDOLE AND BENZOTHIOPHENE COMPOUNDS AS MODULATORS OF THE HISTAMINE H3 RECEPTOR<br/>[FR] COMPOSÉS À BASE D'INDOLE ET DE BENZOTHIOPHÈNE EN TANT QUE MODULATEURS DU RÉCEPTEUR H3 DE L'HISTAMINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2008109333A1

  公开（公告）日：2008-09-12

  [EN] Certain substituted indole and benzothiophene compounds are histamine H₃ receptor modulators useful in the treatment of histamine H₃ receptor-mediated diseases.
  [FR] La présente invention concerne certains composés à base d'indole et de benzothiophène substitués qui sont des modulateurs du récepteur H₃ de l'histamine utiles dans le traitement de maladies médiées par le récepteur H₃ de l'histamine
• Indole- and benzothiophene-based histamine H3 antagonists
  作者：Alejandro Santillan、Kelly J. McClure、Brett D. Allison、Brian Lord、Jamin D. Boggs、Kirsten L. Morton、Anita M. Everson、Diane Nepomuceno、Michael A. Letavic、Alice Lee-Dutra、Timothy W. Lovenberg、Nicholas I. Carruthers、Cheryl A. Grice

  DOI：10.1016/j.bmcl.2010.08.103

  日期：2010.11

  Previous research on histamine H-3 antagonists has led to the development of a pharmacophore model consisting of a central phenyl core flanked by two alkylamine groups. Recent investigation of the replacement of the central phenyl core with heteroaromatic fragments resulted in the preparation of novel 3,5-, 3,6- and 3,7-substituted indole and 3,5-substituted benzothiophene analogs that demonstrate good to excellent hH(3) affinities. Select analogs were profiled in a rat pharmacokinetic model. (C) 2010 Elsevier Ltd. All rights reserved.