Ethyl 5-benzyl-1H,2H,3H,4H,5H-pyrido[4,3-B]indole-2-carboxylate | 688030-07-1

• 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: Ethyl 5-benzyl-1H,2H,3H,4H,5H-pyrido[4,3-B]indole-2-carboxylate
• 英文别名: ethyl 5-benzyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2-carboxylate
• CAS: 688030-07-1
• 化学式: C₂₁H₂₂N₂O₂
• mdl: MFCD27214503
• 分子量: 334.418
• InChiKey: AECBHUJBBDTGRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl 5-benzyl-1H,2H,3H,4H,5H-pyrido[4,3-B]indole-2-carboxylate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 22.0h， 生成 5-benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  γ-Carbolines: binding at 5-HT5A serotonin receptors

  摘要：

  Screening of various agents resulted in the identification of 5-methyl-1,2,3,4-tetrahydro-gamma-carboline (1; K-i = 5,300 nM) as a compound with modest affinity for mouse 5-HT5A receptors. Structure-affinity studies were conducted resulting in 5-methyl-2-[3-(4-fluorophenoxy)propyl]- 1,2,3,4-tetrahydro-gamma-carboline (17; K-i = 13 nM). Although 17 also binds at 5-HT2 receptors, it serves as a novel lead for the further development of 5-HT5A ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00527-8
• 作为产物：
  描述：

  苯肼,盐酸盐 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 Ethyl 5-benzyl-1H,2H,3H,4H,5H-pyrido[4,3-B]indole-2-carboxylate
  参考文献：
  名称：

  γ-Carbolines: binding at 5-HT5A serotonin receptors

  摘要：

  Screening of various agents resulted in the identification of 5-methyl-1,2,3,4-tetrahydro-gamma-carboline (1; K-i = 5,300 nM) as a compound with modest affinity for mouse 5-HT5A receptors. Structure-affinity studies were conducted resulting in 5-methyl-2-[3-(4-fluorophenoxy)propyl]- 1,2,3,4-tetrahydro-gamma-carboline (17; K-i = 13 nM). Although 17 also binds at 5-HT2 receptors, it serves as a novel lead for the further development of 5-HT5A ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00527-8

文献信息

• 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 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLES, METHODS FOR THE PRODUCTION AND THE USE THEREOF<br/>[FR] 2,3,4,5-TÉTRAHYDRO-1H-PYRIDO[4,3-B]INDOLES SUBSTITUÉS AINSI QUE PROCÉDÉS DE LEUR FABRICATION ET LEUR UTILISATION
  申请人：ALLA CHEM LLC

  公开号：WO2008115098A2

  公开（公告）日：2008-09-25

  [EN] The invention relates to novel substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles, to the pharmaceutically acceptable salts and/or hydrates thereof, to methods for the production and the use thereof in the form of biologically active substances, to novel pharmaceutical compositions and medicinal agents which are based thereon, exhibit antihistamine activity and contain, in the form of an active substance, substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles and the pharmaceutically acceptable salts and/or hydrates thereof and to the to methods for the production and the use thereof. The novel substituted 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles and the pharmaceutically acceptable salts and/or hydrates thereof correspond to general formula 1.1, 1.2 or 1.3, wherein, in the compounds of 1.1, R¹ is an amino group substituent selected from hydrogen or optionally substituted C₁-C₅ alkyl; R² is a hydrogen atom or C₁-C₄ alkyl; R³
  [FR] L'invention concerne de nouveaux 2,3,4,5-tétrahydro-1H-pyrido[4,3-b]indoles substitués, leurs hydrates et/ou sels pharmaceutiquement acceptables, des procédés de fabrication et d'utilisation correspondants en qualité de substances biologiquement actives, de nouveaux agents médicaux et compositions pharmaceutiques basés sur ceux-ci, qui manifestent une activité antihistaminique et contiennent comme substance active des 2,3,4,5-tétrahydro-1H-pyrido[4,3-b]indoles substitués ainsi que leurs hydrates et/ou sels pharmaceutiquement acceptables, de même que des procédés de leur fabrication et utilisation. Les nouveaux 2,3,4,5-tétrahydro-1H-pyrido[4,3-b]indoles substitués ainsi que leurs hydrates et/ou sels pharmaceutiquement acceptables correspondent aux formules générales 1.1, 1.2 ou 1.3. Dans ces formules, dans les composés de 1.1, R1 est un substituant du groupe aminé sélectionné parmi l'hydrogène ou l'alkyle C(1)-C(5) éventuellement substitué; R(2) est un atome d'hydrogène ou alkyle C(1)-C(4); R(3)(i) un ou plusieurs substituants similaires ou différents sélectionnés parmi l'hydrogène, l'halogène, l'alkyle C(1)-C(3) ou CF(3); n=0 ou 1-3; dans les composés de 1.2, R(1) est un substituant du groupe aminé sélectionné parmi l'hydrogène ou l'alkyle C(1)-C(5) éventuellement substitué; R(3)(i) un ou plusieurs substituants similaires ou différents sélectionnés parmi l'hydrogène, l'halogène, l'alkyle C(1)-C(3) ou CF(3) et Ar(1) est aryle ou hétérocyclyle contenant au moins un substituant carboxylique et/ou alkyloxycarbonyle ou R(3)(i) est un substituant carboxylique et/ou alkyloxycarbonyle, and Ar(1) est un aryle ou hétérocyclyle éventuellement substitué; dans les composés de 1.3, R(2) est un atome d'hydrogène ou un alkyle C(1)-C(4); R(3)(i) un ou plusieurs substituants similaires ou différents sélectionnés parmi l'hydrogène, l'halogène, l'alkyle C(1)-C(3) ou CF(3) et Ar(2) est un aryle ou hétérocyclyle éventuellement substitué; k=0 ou 1-4; m=1 ou 2.
• [EN] LIGANDS OF a-ADRENOCEPTORS AND OF DOPAMINE, HISTAMINE, IMIDAZOLINE AND SEROTONIN RECEPTORS AND THE USE THEREOF<br/>[FR] LIGANDS DALPHA-ADRÉNORÉCEPTEURS, DE RÉCEPTEURS DE DOPAMINE, DE L'HISTAMINE, D'IMIDAZOLINE ET DE SÉROTONINE AINSI QUE LEURS PROCÉDÉS D'UTILISATION
  申请人：ALLA CHEM LLC

  公开号：WO2009082268A2

  公开（公告）日：2009-07-02

  Данное изобретение относится к новым лигандам, широкий спектр биологической активности которых включает одновременно альфа-адреноцепторы, допаминовые рецепторы, гистаминовые рецепторы, имидазолиновые рецепторы и серотониновые рецепторы, в том числе и серотониновые 5-HT7 рецепторы, представляющим собой соединения общей формулы 1 в виде свободных оснований, геометрических изомеров, рацемических смесей или индивидуальных оптических изомеров, а также в виде фармацевтически приемлемых солей и/или гидратов, где: Rl представляет собой заместитель аминогруппы, в том числе атом водорода, необязательно замещенный C1-C4 алкил, ацил, гетероциклил, алкоксикарбонил, замещенный сульфонил; R2 представляет собой заместитель циклической системы, в том числе атом водорода, атом галогена, необязательно замещенный C1-C4 алкил, CF3, CN, алкокси, алкоксикарбонил, карбоксил, гетероциклил или замещенный сульфонил; Ar - представляет собой необязательно замещенный арил, возможно аннелированный с гетероциклилом, или необязательно замещенный гетероциклил; W представляет собой необязательно замещенную (CH2)m группу, необязательно замещенную CH=CH группу, необязательно замещенную CH2-CH=CH группу, необязательно замещенную G≡С группу, группу SO2; n = 1 или 2; m = 1, 2 или 3; сплошная линия с сопровождающей ее пунктирной линией (---) представляет одинарную или двойную связь. Изобретение также относится к лекарственным субстанциям, фармацевтическим композициям, содержащим в качестве лекарственных субстанций новые лиганды, к новым лекарственным средствам, применяемым для лечения болезней и состояний центральной нервной системы людей и теплокровных животных.
• γ-Carbolines: binding at 5-HT5A serotonin receptors
  作者：Nantaka Khorana、Anil Purohit、Katherine Herrick-Davis、Milt Teitler、Richard A. Glennon

  DOI：10.1016/s0968-0896(02)00527-8

  日期：2003.3

  Screening of various agents resulted in the identification of 5-methyl-1,2,3,4-tetrahydro-gamma-carboline (1; K-i = 5,300 nM) as a compound with modest affinity for mouse 5-HT5A receptors. Structure-affinity studies were conducted resulting in 5-methyl-2-[3-(4-fluorophenoxy)propyl]- 1,2,3,4-tetrahydro-gamma-carboline (17; K-i = 13 nM). Although 17 also binds at 5-HT2 receptors, it serves as a novel lead for the further development of 5-HT5A ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.