2,9-dimethyl-6-[2-(6-methylpyridin-3-yl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole | 1009631-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: 2,9-dimethyl-6-[2-(6-methylpyridin-3-yl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole
• 英文别名: 5-(2-{2,9-Dimethyl-1H,2H,3H,4H,5H,6H-azepino[4,3-B]indol-6-YL}ethyl)-2-methylpyridine；2,9-dimethyl-6-[2-(6-methylpyridin-3-yl)ethyl]-1,3,4,5-tetrahydroazepino[4,3-b]indole
• CAS: 1009631-99-5
• 化学式: C₂₂H₂₇N₃
• mdl: MFCD27214441
• 分子量: 333.476
• InChiKey: MOAZAZMSTNXWJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  9-methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole 在 四正丁基硫酸铵 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 48.5h， 生成 2,9-dimethyl-6-[2-(6-methylpyridin-3-yl)ethyl]-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Bioisosteric Analogues of Dimebon™

  摘要：

  本文介绍了一系列新型 6,9-二取代 2-甲基-1,2,3,4,5,6-六氢氮杂卓[4,3-b]吲哚的合成和生物学评价。这些化合物是 Dimebon ™ 的独特生物异构类似物，对包括一些 GPCR 家族成员在内的各种靶标具有良好的生物活性。

  DOI：

  10.2174/157018010791306579

文献信息

• SUBSTITUTED AZEPINO[4,3-B]INDOLES, PHARMACOLOGICAL COMPOSITION AND A METHOD FOR THE PRODUCTION AND USE THEREOF
  申请人：Borisovich Frolov Yevgeniy

  公开号：US20120040965A1

  公开（公告）日：2012-02-16

  The invention relates to novel chemical compounds, searching for novel physiologically active substances, leader compounds, “molecular tools”, and drug candidates obtained on the basis of screening of combinatorial and focused libraries of the said compounds, and also to pharmaceutical composition, methods for preparation and use thereof. The invention proposes hydrogenated azepino[4,3-b]indoles of general formula 1 or racemates, optical isomers, geometrical isomers, mixtures of optical or geometrical isomers, pharmaceutically acceptable salts and/or hydrates thereof: wherein: solid line together with the dotted line ( ) represents a single or double bond; R 1 and R 2 independently of each other are amino group substituents selected from hydrogen; optionally substituted C 1 -C 8 alkyl with substituents selected from optionally substituted aryl or 5-6-membered azaheterocyclyl; C 1 -C 8 alkoxycarbonyl; optionally substituted phenyl; optionally substituted carbonylamino or thiocarbonylamino; substituted acyl; C 1 -C 8 alkylsulfonyl; optionally substituted arylsulfonyl; upon that, the substituents in the said R 1 and R 2 independently selected from C 1 -C 8 alkyl, halogen atoms, nitro group, carboxy group, alkoxy, aryl; R i n represents one or more “substituents of cyclic structure” of the same or different structure selected from hydrogen, halogen, C 1 -C 8 alkyl, C 6 -C 10 aryl, 5-6-membered azaheterocyclyl.

  本发明涉及新型化合物，寻找新的生理活性物质，领先化合物，“分子工具”和药物候选物，这些化合物是基于筛选所述化合物的组合和专注库获得的，并且还涉及制备和使用其药物组合物的方法。 本发明提出了通式1的氢化氮杂七环[4,3-b]吲哚或外消旋体、光学异构体、几何异构体、光学或几何异构体的混合物、药学上可接受的盐和/或水合物： 其中：实线和虚线（）表示单键或双键；R1和R2独立地是氨基基团取代物，选自氢原子；可选取代的C1-C8烷基，所述取代基被选自可选取代的芳基或5-6成员的杂氮杂环基；C1-C8烷氧羰基；可选取代的苯基；可选取代的羰基氨基或硫代羰基氨基；取代的酰基；C1-C8烷基磺酰基；可选取代的芳基磺酰基；在此基础上，所述R1和R2中的取代基独立地选自C1-C8烷基、卤原子、硝基、羧基、烷氧基、芳基；Rin代表相同或不同结构的一个或多个“环结构取代基”，选自氢原子、卤素、C1-C8烷基、C6-C10芳基、5-6成员的杂氮杂环基。
• LIGANDS OF ALPHA-ADRENOCEPTORS, DOPAMINE, HISTAMINE, IMIDAZOLINE AND SEROTONIN RECEPTORS AND THEIR USE
  申请人：Ivashchenko Andrey Alexandrovich

  公开号：US20110039825A1

  公开（公告）日：2011-02-17

  The invention relates to novel ligands the broad spectrum of biological activity of which includes simultaneously α-adrenoceptors, dopamine receptors, histamine receptors, imidazoline receptors and serotonin receptors, among them serotonin 5-HT 7 receptors, which are compounds of general formula 1 in the form of free bases, geometrical isomers, racemic mixtures or individual optical isomers, pharmaceutically acceptable salts and/or hydrates, wherein: R1 is a substituent of amino group, selected from hydrogen, optionally substituted C 1 -C 4 alkyl, acyl, heterocyclyl, alkoxycarbonyl, substituted sulfonyl; R2 is a substituent of cyclic system, selected from hydrogen, halogen, optionally substituted C 1 -C 4 alkyl, CF 3 , CN, alkoxy, alkoxycarbonyl, carboxyl, heterocyclyl or substituted sulfonyl; Ar is optionally substituted aryl not necessarily annalated with heterocyclyl, or optionally substituted aromatic heterocyclyl; W is optionally substituted (CH 2 ) m group, optionally substituted CH═CH group, optionally substituted CH 2 —CH═CH group, C≡C group, SO 2 group; n=1, 2; m=1, 2, 3; solid line accompanied by dotted line, i.e. may represent single or double bond. The invention also relates to active ingredients, pharmaceutical compositions comprising the said ligands as active ingredients; to novel medicaments useful for treatment of diseases and conditions of central nervous system (CNS) of humans and warm-blooded animals.
• [EN] SUBSTITUTED AZEPINO[4,3-B]INDOLES, PHARMACOLOGICAL COMPOSITION AND A METHOD FOR THE PRODUCTION AND USE THEREOF<br/>[FR] AZÉPINO[4,3-B]INDOLES SUBSTITUÉS, COMPOSITION PHARMACEUTIQUE, PROCÉDÉ DE FABRICATION ET D'UTILISATION
  申请人：ALLA CHEM LLC

  公开号：WO2008024029A1

  公开（公告）日：2008-02-28

  [EN] The invention relates to synthesising novel chemical agents, to searching novel physiologically active substances, leading compounds, "molecular tools" and drug candidates produced by screening combinatorial and focused libraries of compounds, to a pharmaceutical composition and to methods for the production and use thereof. The invention claims hydrated substituted azepino[4,3-b]indoles of general formula 1, the racemates, optical and geometrical isomers and the pharmaceutically acceptable salts and/or hydrates thereof, wherein a dotted line with an unbroken line associated therewith (__----) is a single or double bond; R¹ and R² independently of one another represent aminogroup substituents selected from hydrogen; from possibly substituted C₁-C₈ alkyl, possibly substituted by aryl, 5-6-membered azaheterocyclyl; from C₁-C₈ alkoxycarbonyl; from possibly substituted phenyl; possibly carbonylamino or tiocarbonylamino substituted; from substituted acyl, C₁-C₈ alkylsulphonyl, possibly substituted arylsulphonyl; wherein substituents in said R₁ and R₂ are independently selected from C₁-C₈ alkyl, halogen atoms, nitro, carboxy and alkoxy aryl; R _{ⁱ
  [FR] La présente invention concerne la synthèse de nouvelles substances chimiques, la recherche de nouvelles substances physiologiquement actives, de composés principaux, d'"outils moléculaires" et de médicaments candidats obtenus par le criblage de bibliothèques focalisées ou combinatoires, de même qu'une composition pharmaceutique ainsi que des procédés de leur fabrication. L'invention porte sur des azépino[4,3-b]indoles possédant la formule générale 1, sur leurs racémates, leurs isomères géométriques, leurs sels et/ou hydrates pharmaceutiquement acceptables. Dans la formule (1), la ligne tiretée avec une ligne ininterrompue (------) désigne une liaison simple ou double; R¹ et R² sont indépendamment des substitutifs de groupe aminé sélectionné parmi hydrogène; un alkyle C1-C8 éventuellement substitué par un aryle; un azahétérocyclyle à 5 ou 6 éléments; un alkoxycarbonyle C1-C8; un phényle éventuellement substitué; des carbonylamino ou tiocarbonylamino éventuellement substitués; un acyle substitué; un alkylsulphonyle C1-C8; un arylsulphonyle éventuellement substitué; les substitutifs dans R¹ et R² sont sélectionné indépendamment parmi un alkyle C1-C8, des atomes d'halogène, nitro, carboxy, alkoxy et aryle; R ⁱ}
• Synthesis and Biological Evaluation of Novel Bioisosteric Analogues of Dimebon&amp;#8482;
  作者：Alexandre Vasilevich Ivachtchenko、Eugene Borisovich Frolov、Oleg Dmitrievich Mitkin、Sergey Evgenevich Tkachenko、Alexandre Khvat

  DOI：10.2174/157018010791306579

  日期：2010.7.1

  In the present paper, we describe the synthesis and biological evaluation for a series of novel 6,9-disubstituted 2-methyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indoles. These compounds represent unique bioisosteric analogues of Dimebon ™ with promising biological activity against a panel of various targets including some GPCR family members.

  本文介绍了一系列新型 6,9-二取代 2-甲基-1,2,3,4,5,6-六氢氮杂卓[4,3-b]吲哚的合成和生物学评价。这些化合物是 Dimebon ™ 的独特生物异构类似物，对包括一些 GPCR 家族成员在内的各种靶标具有良好的生物活性。