2,3,4,5-tetrahydro-2,6,8-trimethyl-1H-pyrido[4,3-b]indole | 17223-51-7

• 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: 2,3,4,5-tetrahydro-2,6,8-trimethyl-1H-pyrido[4,3-b]indole
• 英文别名: 2,6,8-Trimethyl-2,3,4,5-tetrahydro-1H-pyrido<4,3-b>indol；2,6,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2,6,8-Trimethyl-1,3,4,5-tetrahydropyrido[4,3-b]indole
• CAS: 17223-51-7
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: LQWPJKPUTGNACX-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  352.3±37.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  6-溴喹啉 、 2,3,4,5-tetrahydro-2,6,8-trimethyl-1H-pyrido[4,3-b]indole 在 potassium phosphate 、 copper(l) iodide 、 L-脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,6,8-trimethyl-5-quinolin-6-yl-3,4-dihydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  [EN] PYRIDO[4,3-B]INDOLE AND PYRIDO[3,4-B]INDOLE DERIVATIVES AND METHODS OF USE
  [FR] DÉRIVÉS DE PYRIDO[4,3-B]INDOLE ET DE PYRIDO[3,4-B]INDOLE ET PROCÉDÉS D'UTILISATION

  摘要：

  本公开涉及四环吡啶并[4,3-b]吲哚和吡啶[3,4-b]吲哚。还提供了包含这些化合物的药物组合物，以及使用这些化合物进行各种治疗应用的方法，包括治疗认知障碍、精神病性障碍、神经递质介导的障碍和/或神经元障碍。

  公开号：

  WO2011103430A1
• 作为产物：
  描述：

  3-(2-Azido-3,5-dimethylphenyl)-1-methylpyridin-1-ium trifluoromethanesulfonate 在 sodium tetrahydroborate 、 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 2,3,4,5-tetrahydro-2,6,8-trimethyl-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  钌催化芳基叠氮化物形成 γ-碳鎓离子；二甲酚的合成

  摘要：

  通过 3-吡啶基取代的芳基叠氮化物的钌 (III) 催化反应，立体选择性地生产一系列 γ-咔啉。其他催化剂和条件既没有那么选择性，也没有那么高产率。该方法用于简洁、高效地合成二甲苯啉。

  DOI：

  10.1021/ol2008268

文献信息

• COMPOUNDS AND METHODS FOR TREATMENT OF HYPERTENSION
  申请人：Medivation Technologies, Inc.

  公开号：US20150266884A1

  公开（公告）日：2015-09-24

  Hydrogenated pyrido[4,3-b]indoles, pyrido[3,4-b]indoles and azepino[4,5-b]indoles are described. The compounds may bind to and are adrenergic receptor α 2B antagonists. The compounds may also bind to and antagonize adrenergic receptor α 1B . The compounds may find use in therapy, e.g., to (i) reduce blood pressure and/or (ii) promote renal blood flow and/or (iii) decrease or inhibit sodium reabsorption. The compounds may also be used to treat diseases or conditions that are, or are expected to be, responsive to a decrease in blood pressure. Use of the compounds to treat cardiovascular and renal disorders is particularly described.

  氢化吡啶并[4,3-b]吲哚，吡啶[3,4-b]吲哚和氮杂七元[4,5-b]吲哚被描述。这些化合物可能与肾上腺素受体α2B结合并拮抗。这些化合物也可能与肾上腺素受体α1B结合并拮抗。这些化合物可能在治疗中发挥作用，例如（i）降低血压和/或（ii）促进肾脏血流和/或（iii）减少或抑制钠重吸收。这些化合物也可用于治疗对降低血压有反应或预期会有反应的疾病或症状。特别描述了使用这些化合物治疗心血管和肾脏疾病。
• 1,2,3,4-Tetrahydro-γ-carbolinium salts: novel reactions with thiols, mediated by polymer-supported reagents
  作者：Mike E. Lizarzaburu、Stephen J. Shuttleworth

  DOI：10.1016/j.tetlet.2004.04.078

  日期：2004.6

  A series of dialkyl-[2-(3-alkylsulfanylmethyl-1H-indol-2-yl)-ethyl]amines was produced using a novel route involving nucleophilic ring opening of 2,2-dialkyl-1,2,3,4-tetrahydro-γ-carbolinium salts with thiols. The insertion reaction was mediated by a strong, polymer-supported base, and the purification of the target compounds was facilitated using resin-bound sulfonic acid.

  使用涉及2,2-二烷基-1,2,3,4的亲核开环的新途径制备了一系列二烷基-[2-（3-烷基硫烷基甲基-1 H-吲哚-2-基）-乙基]胺-四氢-γ-碳鎓盐与硫醇。插入反应由牢固的聚合物支撑的碱介导，并且使用树脂结合的磺酸促进目标化合物的纯化。
• [EN] COMPOUNDS AND METHODS OF TREATING DIABETES<br/>[FR] COMPOSÉS ET PROCÉDÉS DE TRAITEMENT DU DIABÈTE
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2012112962A1

  公开（公告）日：2012-08-23

  Hydrogenated pyrido[4,3-b]indoles, pyrido [3, 4-b] indoles and azepino[4,5-b]indoles are described. The compounds may bind to and are antagonists of the adrenergic receptor a2A. The compounds may also bind to and are an antagonist of the adrenergic receptor α2B ; or the compounds are not antagonists of the adrenergic receptor α2β and the compounds are administered in conjunction with a second agent that reduces, or is expected to reduce, blood pressure in an individual. The compounds may find use in therapy, e.g., to regulate blood glucose level, increase insulin secretion and treat diseases or conditions that are, or are expected to be, responsive to an increase in insulin production. Use of the compounds to treat type 2 diabetes is particularly described.

  氢化吡啶并[4,3-b]吲哚，吡啶[3,4-b]吲哚和氮杂七环[4,5-b]吲哚已被描述。这些化合物可能与肾上腺素受体α2A结合并起拮抗作用。这些化合物也可能与肾上腺素受体α2B结合并起拮抗作用；或者这些化合物不是肾上腺素受体α2β的拮抗剂，这些化合物与第二种降低或预计会降低个体血压的药物一同给予。这些化合物可能在治疗中发挥作用，例如，调节血糖水平，增加胰岛素分泌并治疗疾病或病情，这些疾病或病情对胰岛素产生增加有反应或预计会有反应。特别描述了使用这些化合物治疗2型糖尿病。
• COMPOUNDS AND METHODS OF TREATING DIABETES
  申请人：Protter Andrew Asher

  公开号：US20130053367A1

  公开（公告）日：2013-02-28

  Hydrogenated pyrido[4,3-b]indoles, pyrido[3,4-b]indoles and azepino[4,5-b]indoles are described. The compounds may bind to and are antagonists of the adrenergic receptor α 2A . The compounds may also bind to and are an antagonist of the adrenergic receptor α 2B ; or the compounds are not antagonists of the adrenergic receptor α 2B and the compounds are administered in conjunction with a second agent that reduces, or is expected to reduce, blood pressure in an individual. The compounds may find use in therapy, e.g., to regulate blood glucose level, increase insulin secretion and treat diseases or conditions that are, or are expected to be, responsive to an increase in insulin production. Use of the compounds to treat type 2 diabetes is particularly described.

  本文描述了氢化吡啶并[4,3-b]吲哚、吡啶[3,4-b]吲哚和氮杂七环[4,5-b]吲哚。这些化合物可以结合并拮抗肾上腺素受体α2A。这些化合物也可以结合并拮抗肾上腺素受体α2B；或这些化合物不是肾上腺素受体α2B的拮抗剂，并且这些化合物与第二个降低或预计降低个体血压的药物一起使用。这些化合物可以用于治疗，例如，调节血糖水平、增加胰岛素分泌和治疗对增加胰岛素产生有反应或预计会有反应的疾病或病况。特别描述了使用这些化合物治疗2型糖尿病的用途。
• COMPOUNDS AND METHODS FOR TREATING DIABETES
  申请人：Medivation Technologies, Inc

  公开号：US20130190294A1

  公开（公告）日：2013-07-25

  Hydrogenated pyrido[4,3-b]indoles, pyrido[3,4-b]indoles and azepino[4,5-b]indoles are described. The compounds may bind to and are antagonists of the adrenergic receptor α 2A . The compounds may also bind to and are an antagonist of the adrenergic receptor α 2B ; or the compounds are not antagonists of the adrenergic receptor α 2B and the compounds are administered in conjunction with a second agent that reduces, or is expected to reduce, blood pressure in an individual. The compounds may find use in therapy, e.g., to regulate blood glucose level, increase insulin secretion and treat diseases or conditions that are, or are expected to be, responsive to an increase in insulin production. Use of the compounds to treat type 2 diabetes is particularly described.

  本文描述了氢化吡啶[4,3-b]吲哚、吡啶[3,4-b]吲哚和氮杂七环[4,5-b]吲哚。这些化合物可以结合并拮抗肾上腺素α2A受体。这些化合物也可以结合并拮抗肾上腺素α2B受体；或者这些化合物不是肾上腺素α2B受体的拮抗剂，并且这些化合物与第二种降低或预计降低个体血压的药物一起使用。这些化合物可以在治疗中发挥作用，例如，调节血糖水平、增加胰岛素分泌并治疗对增加胰岛素产生反应的疾病或情况。本文特别描述了使用这些化合物治疗2型糖尿病的方法。