2,7-dimethyl-3,4-dihydro-1H-pyrrolo[3,4-b]indole | 1009836-81-0

• 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: 2,7-dimethyl-3,4-dihydro-1H-pyrrolo[3,4-b]indole
• 英文别名: 2,7-Dimethyl-3,4-dihydro-1h-pyrrolo-[3,4-b]indole
• CAS: 1009836-81-0
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: JKOFQFTWHDXXME-UHFFFAOYSA-N

物化性质

• 沸点：
  306.7±37.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,7-dimethyl-3,4-dihydro-1H-pyrrolo[3,4-b]indole 在 platinum(IV) oxide 、 氢气 、 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 24.0h， 生成 (3aS,8bS)-2,7-dimethyl-4-[2-(6-methylpyridin-3-yl)ethyl]-1,3,3a,8b-tetrahydropyrrolo[3,4-b]indole
  参考文献：
  名称：

  Synthesis of hydrogenated 2,7-dimethylpyrrolo[3,4-b]indoles – analogs of dimebon

  摘要：

  A schemes have been proposed for the synthesis of novel 4-substituted 2,7-dimethyl-3,4-dihydro-1H- and previously unknown 2,7-dimethyl-cis-1,2,3,3a,4,8b-hexahydropyrrolo[3,4-b]indoles. In the case of the Dimebon structural analog 2,7-dimethyl-4-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1H-pyrrolo-[3,4-b]indole a broad spectrum of pharmacological activity was found in the hydrogenated pyrroloindoles suitable for the development of medicines via the "magic bullet" concept. A strong dependence of the antagonist relationship of the synthesized compounds towards histamine H-1 and serotonin 5-HT6 receptors with the nature of the substituent in the 4 position and the degree of hydrogenation of the pyrrolo[3,4-b]indoles was demonstrated.

  DOI：

  10.1007/s10593-010-0488-z
• 作为产物：
  描述：

  1-乙氧羰基吡咯烷-3-酮 在 lithium aluminium tetrahydride 、 磷酸 、 sodium acetate 作用下， 以 乙醚 、 水 为溶剂， 反应 3.0h， 生成 2,7-dimethyl-3,4-dihydro-1H-pyrrolo[3,4-b]indole
  参考文献：
  名称：

  Synthesis of hydrogenated 2,7-dimethylpyrrolo[3,4-b]indoles – analogs of dimebon

  摘要：

  A schemes have been proposed for the synthesis of novel 4-substituted 2,7-dimethyl-3,4-dihydro-1H- and previously unknown 2,7-dimethyl-cis-1,2,3,3a,4,8b-hexahydropyrrolo[3,4-b]indoles. In the case of the Dimebon structural analog 2,7-dimethyl-4-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1H-pyrrolo-[3,4-b]indole a broad spectrum of pharmacological activity was found in the hydrogenated pyrroloindoles suitable for the development of medicines via the "magic bullet" concept. A strong dependence of the antagonist relationship of the synthesized compounds towards histamine H-1 and serotonin 5-HT6 receptors with the nature of the substituent in the 4 position and the degree of hydrogenation of the pyrrolo[3,4-b]indoles was demonstrated.

  DOI：

  10.1007/s10593-010-0488-z

文献信息

• LIGANDS OF 5-HT6 RECEPTORS, A PHARMACEUTICAL COMPOSITION, METHOD FOR THE PRODUCTION AND USE THEREOF
  申请人：Alla Chem, LLC.

  公开号：EP2184064A2

  公开（公告）日：2010-05-12

  The invention relates to novel ligands of 5-HT6 receptor, to a pharmaceutical composition containing said novel ligands of 5-HT6 receptor as active component and to novel medicaments used for humans and warm-blooded animals for treating diseases and conditions of central nervous system, in pathogenesis of which neuromediator systems induced by 5-HT6 receptors are playing an essential role. Azaheterocyclic compounds of the general formula 1 or racemates, or optical or geometrical isomers, or pharmaceutically acceptable salts and/or hydrates thereof are used as 5-HT6 ligands. Wherein R2 and R3 independently of each other represent an amino group substituent selected from hydrogen; substituted carbonyl; substituted aminocarbonyl; substituted aminothiocarbonyl; substituted sulphonyl; C1-C5-alkyl optionally substituted by: C6-C10-arylaminocarbonyl, heterocyclyl, C6-C10-arylaminocarbonyl, C6-C10-arylaminothiocarbonyl, C5-C10-azaheteroaryl, optionally substituted carboxyl, nitryl group, optionally substituted aryl; R1k represents from 1 to 3 substituents of cyclic system, independent of each other and selected from hydrogen, optionally substituted C1-C5-alkyl, C1-C5-alkoxy, C1-C5-alkenyl, C1-C5-alkynyl, halogen, trifluoromethyl, CN-group, carboxyl, optionally substituted aryl, optionally substituted heterocyclyl, substituted sulfonyl, optionally substituted carboxyl; the solid line accompanied by the dotted line (---) represents a single or a double bond; n=1,2 or 3.

  本发明涉及 5-HT6 受体的新型配体、含有所述 5-HT6 受体新型配体作为活性成分的药物组合物以及用于人类和温血动物治疗中枢神经系统疾病和病症的新型药物，在中枢神经系统疾病和病症的发病机制中，5-HT6 受体诱导的神经介导系统发挥着重要作用。 通式 1 的杂杂环化合物或外消旋体，或光学或几何异构体，或其药学上可接受的盐和/或水合物可用作 5-HT6 配体。 其中，R2 和 R3 相互独立地代表一个氨基取代基，该取代基选自氢；取代的羰基；取代的氨基羰基；取代的氨基硫代羰基；取代的磺酰基；任选被以下取代的 C1-C5- 烷基：C6-C10-芳基氨基羰基：C6-C10-芳基氨基羰基、杂环烷基、C6-C10-芳基氨基羰基、C6-C10-芳基氨基硫代羰基、C5-C10-氮杂环芳基、任选取代的羧基、硝基、任选取代的芳基；R1k 代表 1 至 3 个相互独立的环状体系取代基，选自氢、任选取代的 C1-C5- 烷基、C1-C5-烷氧基、C1-C5-烯基、C1-C5-炔基、卤素、三氟甲基、CN 基、羧基、任选取代的芳基、任选取代的杂环基、取代的磺酰基、任选取代的羧基；伴随虚线 (---) 的实线代表单键或双键；n=1、2 或 3。
• [EN] SUBSTITUTED PYRROLO[4,3-B]INDOLES, COMBINATORIAL AND FOCUSED LIBRARIES, PHARMACOLOGICAL COMPOSITION AND A METHOD FOR THE PRODUCTION AND USE THEREOF<br/>[FR] PYRROLO[4,3-B]INDOLES SUBSTITUÉS, BIBLIOTHÈQUES FOCALISÉES OU COMBINATOIRES, COMPOSITION PHARMACEUTIQUE, PROCÉDÉ DE FABRICATION ET D'UTILISATION
  申请人：ALLA CHEM LLC

  公开号：WO2008026965A1

  公开（公告）日：2008-03-06

  [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 pyrrolo[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, of possibly substituted C₁-C₆ alkyl, possibly substituted by aryl, by hydrogen-containing heteroaryl; from C₁-C₆ alkoxycarbonyl, possibly substituted phenyl, possibly carbonylamino or tiocarbonylamino substituted, substituted acyl, possibly substituted arylsulphonyl; R ⁱ _n
  [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 pyrrolo[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-C6 éventuellement substitué par un aryle; un azahétérocyclyle à 5 ou 6 éléments; un alkoxycarbonyle C1-C6; un phényle éventuellement substitué; des carbonylamino ou tiocarbonylamino éventuellement substitués; un acyle substitué; un arylsulphonyle éventuellement substitué; R ⁱ _n
• [EN] LIGANDS OF 5-HT6 RECEPTORS, A PHARMACEUTICAL COMPOSITION, METHOD FOR THE PRODUCTION AND USE THEREOF<br/>[FR] LIGAND DES RÉCEPTEURS 5-HT6, COMPOSITION PHARMACEUTIQUE ET PROCÉDÉ DE FABRICATION ET D'UTILISATION
  申请人：ALLA CHEM LLC

  公开号：WO2008060190A2

  公开（公告）日：2008-05-22

  [EN] The invention relates to novel ligands of 5-HT₆ receptor, to a pharmaceutical composition containing said novel ligands of 5-HT₆ receptor in the form of an active component and to novel medicinal preparations which are used for human beings and homoiotherms for treating diseases and states of the central nervous system, in the pathogenesis of which neurotransmitter systems modulated by 5-HT₆ receptors play a substantial role. Asaheterocyclic compound of general formula 1 or the racemates thereof or the optical or geometrical isomers thereof, or the pharmaceutically acceptable salts and/or hydrates thereof are used in the form of 5-HT₆ ligands. Wherein R2 and R3 independently from each other represent an aminogroup substituent selected from hydrogen, substituted carbonyl, substituted aminocarbonyl, substituted aminothiocarbonyl, substituted sulphonyl, C₁-C₅-alkyl optionally substituted by C₆-C₁₀-arylaminocarbonyl, optionally substituted by heterocyclyl, by C₆-C₁₀- arylaminocarbonyl, by C₆-C₁₀ -arylaminothiocarbonyl, by C₅-C₁₀-azaheteroaryl, optionally substituted by carboxyl, by a nitryl group and optionally substituted aryl; R¹ _k
  [FR] La présente invention concerne de nouveaux ligands du récepteur de sérotonine 5-HT₆, une composition pharmaceutique contenant en tant que principe actif de nouveaux ligands du récepteur de sérotonine 5-HT_6, de nouvelles formulations destinées aux humains ou aux animaux à sang chaud, qui s'utilisent dans le traitement de maladies et d'états du système nerveux central dans la pathogénèse desquels un rôle important est joué par des systèmes neuromédiateurs, modulés par les récepteurs 5-HT_6.On propose d'utiliser en tant que récepteur 5-HT₆des compositions aza-hétérocyliques correspondant à la formule générale (1) ou leurs racémates ou leurs isomères optiques ou leurs isomères géométriques ou leurs sels et/ou hydrates pharmaceutiquement acceptables (formule 1), dans laquelle R2 et R3 sont indépendamment un substituant de groupe amino sélectionné parmi hydrogène; carbonyle substitué; aminocarbonyle substitué; aminothiocarbonyle substitué; sulfonyle substitué; alkyle C₁-C₅éventuellement substitué par aryle C₆-C₁₀, éventuellement substitué par hétérocycle, par arylaminocarbonyle C₆-C₁₀, par arylaminothiocarbonyle C₆-C₁₀, par azahétéroaryle C₆-C₁₀, éventuellement substitué par carboxyle, par groupe nitryle, par aryle éventuellement substitué; et R¹ _k
• Synthesis of hydrogenated 2,7-dimethylpyrrolo[3,4-b]indoles – analogs of dimebon
  作者：A. V. Ivachtchenko、E. B. Frolov、O. D. Mitkin、S. E. Tkachenko、A. V. Khvat

  DOI：10.1007/s10593-010-0488-z

  日期：2010.6

  A schemes have been proposed for the synthesis of novel 4-substituted 2,7-dimethyl-3,4-dihydro-1H- and previously unknown 2,7-dimethyl-cis-1,2,3,3a,4,8b-hexahydropyrrolo[3,4-b]indoles. In the case of the Dimebon structural analog 2,7-dimethyl-4-[2-(6-methylpyridin-3-yl)ethyl]-3,4-dihydro-1H-pyrrolo-[3,4-b]indole a broad spectrum of pharmacological activity was found in the hydrogenated pyrroloindoles suitable for the development of medicines via the "magic bullet" concept. A strong dependence of the antagonist relationship of the synthesized compounds towards histamine H-1 and serotonin 5-HT6 receptors with the nature of the substituent in the 4 position and the degree of hydrogenation of the pyrrolo[3,4-b]indoles was demonstrated.