2,3,4,9-四氢-6-羟基-1H-吡啶并[3,4-b]吲哚-1-酮 | 51085-95-1

• 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
• 中文名称: 2,3,4,9-四氢-6-羟基-1H-吡啶并[3,4-b]吲哚-1-酮
• 英文名称: 6-hydroxy-3,4-dihydro-1-oxo-β-carboline
• 英文别名: kb-NB123-59；2,3,4,9-Tetrahydro-6-hydroxy-1H-pyrido(3,4-b)indol-1-one；6-hydroxy-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
• CAS: 51085-95-1
• 化学式: C₁₁H₁₀N₂O₂
• mdl: MFCD09036260
• 分子量: 202.213
• InChiKey: WNGPRJOWLUNBCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,3,4,9-四氢-6-羟基-1H-吡啶并[3,4-b]吲哚-1-酮 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 17,17-Dimethyl-14-oxa-6,9-diazapentacyclo[11.8.0.02,10.03,8.015,20]henicosa-1(13),2(10),3(8),11,15(20)-pentaene-7,19-dione
  参考文献：
  名称：

  2,3,4,9-Tetrahydro-1H-xanthen-1-ones 和 8,9,10,12-Tetrahydro-11H-benzo[a]xanthen-11-ones 通过捕获 ofo-Quinone 的简便方法方法论

  摘要：

  摘要 2,3,4,9-四氢-1H-xanthene-1-ones 和 8,9,10,12-四氢-11H-benzo[a]xanthene-11-ones 的一种高效、简单的合成方法报道了- 3-二甲氨基-2-环己烯-1-酮与羟基苄醇、苯酚和2-萘酚曼尼希碱或其季铵化衍生物的锅缩合。据信该反应的机理涉及邻醌甲基化物中间体的形成。图形概要

  DOI：

  10.1080/00397911.2010.545164
• 作为产物：
  描述：

  6-(benzyloxy)-2,3,4,9-tetrahydro-1H-β-carbolin-1-one 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2,3,4,9-四氢-6-羟基-1H-吡啶并[3,4-b]吲哚-1-酮
  参考文献：
  名称：

  From pyrroles to 1-oxo-2,3,4,9-tetrahydro-1H-β-carbolines: A new class of orally bioavailable mGluR1 antagonists

  摘要：

  Exploiting the SAR of the known pyrrole derivatives, a new class of mGluR1 antagonists was designed by replacement of the pyrrole core with an indole scaffold and consequent cyclization of the C-2 position into a tricyclic beta-carboline template. The appropriate exploration of the position C-6 with a combination of H-bond acceptor groups coupled with bulky/lipophilic moieties led to the discovery of a new series of mGluR1 antagonists. These compounds exhibited a non-competitive behavior, excellent pharmacokinetic properties, and good in vivo activity in animal models of acute and chronic pain, after oral administration. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.055

文献信息

• [EN] 8-TRIAZOLYLXANTHINE DERIVATIVES, PROCESSES FOR THEIR PRODUCTION AND THEIR USE AS ADENOSINE RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS DE 8-TRIAZOLYLXANTHINE, LEURS PROCÉDÉS DE FABRICATION ET LEUR UTILISATION EN TANT QU'AGONISTES DE RÉCEPTEURS DE L'ADÉNOSINE
  申请人：LIFE & BRAIN GMBH

  公开号：WO2012076974A1

  公开（公告）日：2012-06-14

  The invention relates to derivatives of the general formulae (I) and (II) to processes for the production thereof, to pharmaceutical preparations containing said compounds and/or physiologically compatible salts or solvates or prodrugs which can be produced therefrom as well as to the pharmaceutical use of said compounds, the salts or solvates thereof as adenosine receptor antagonists, in particular for the treatment of neurodegenerative disorders, e.g. stroke, amylotrophic lateral sclerosis, dementia, Alzheimer's disease, Parkinson's disease, ischemia/reperfusion injury, inflammation, and/or neurological disorder. The blockade of adenosine receptors could also be useful for other indications regarding the metabolism, e.g. diabetic retinopathy, diabetes mellitus, hyperbaric oxygen - induced retinopathy and/or obesity. Applications could also be the treatment of allergic diseases and autoimmune diseases, including mast cell degranulation, asthma, bronchoconstriction, pulmonary fibrosis, inflammatory or obstructive airways disease and/or chronic obstructive pulmonary disease (COPD). In addition, they could be used to treat cancer. The diseases associated with adenosine receptors are also diabetes, diarrhea, inflammatory bowel disease and/or gastrointestinal tract disorders. Adenosine receptor antagonists could be effective for treating a hepatic disease or condition for reducing fat deposition in the liver or fibrosis of the liver. The use of compounds of general formulae I or II can be associated with many applications e.g., scleroderm arthritis, atherosclerosis, urticaria, myocardial infarction, myocardial reperfusion after ischemia, vasodilation, hypertension, hypersensitivity, myocardial ischemia, heart attack and/or retinopathy of prematurity.

  本发明涉及具有通用公式(I)和(II)的衍生物，以及它们的制备方法，含有所述化合物的药物制剂以及/或可以从它们产生的生理上相容的盐或溶剂化物或前药，以及所述化合物、其盐或溶剂化物作为腺苷受体拮抗剂的药物用途，特别是用于治疗神经退行性疾病，例如中风、肌萎缩性侧索硬化症、痴呆、阿尔茨海默病、帕金森病、缺血/再灌注损伤、炎症和/或神经系统疾病。阻断腺苷受体对于涉及代谢的其他适应症也可能有用，例如糖尿病视网膜病变、糖尿病、高氧诱导视网膜病变和/或肥胖。应用还可以包括治疗过敏性疾病和自身免疫性疾病，包括肥大细胞脱粒、哮喘、支气管收缩、肺纤维化、炎症性或阻塞性气道疾病和/或慢性阻塞性肺病（COPD）。此外，它们还可以用于治疗癌症。与腺苷受体相关的疾病还包括糖尿病、腹泻、炎症性肠病和/或胃肠道疾病。腺苷受体拮抗剂可能对治疗肝病或减少肝脏脂肪沉积或肝脏纤维化有效。通用公式I或II的化合物的使用可以与许多应用相关联，例如，硬皮病关节炎、动脉硬化、荨麻疹、心肌梗死、缺血后心肌再灌注、血管舒张、高血压、过敏反应、心肌缺血、心脏病发作和/或早产儿视网膜病变。
• Beta-carboline compounds and analogues thereof as mitogen-activated protein kinase-activated protein kinase-2 inhibitors
  申请人：Anderson R. David

  公开号：US20050137220A1

  公开（公告）日：2005-06-23

  A method is described for inhibiting mitogen activated protein kinase-activated protein kinase-2 in a subject in need of such inhibition, where the method involves administering to the subject a beta-carboline MK-2 inhibiting compound, or a pharmaceutically acceptable salt thereof.

  本文描述了一种用于抑制需要这种抑制的受试者中的有丝分裂原活化蛋白激酶激活蛋白激酶-2的方法，其中该方法涉及向受试者施用一种β-喀啉MK-2抑制化合物或其药学上可接受的盐。
• PROTEIN KINASE D INHIBITORS
  申请人：Wipf Peter

  公开号：US20140045821A1

  公开（公告）日：2014-02-13

  Compounds according to Formula (I), are potent inhibitors of protein kinase D (pan-PKD) activity. PKD controls key signaling cascades in cells, affecting cell proliferation, gene transcription, and protein trafficking. Accordingly, pharmaceutically acceptable compositions of the inventive compounds are candidate therapeutics for pathological conditions conditioned by changes in PKD activity.

  根据式(I)，化合物是蛋白激酶D(pan-PKD)活性的有效抑制剂。PKD控制着细胞中的关键信号级联，影响细胞增殖、基因转录和蛋白质运输。因此，这些创新化合物的药学合适组合物是治疗PKD活性改变引起的病理情况的候选药物。
• METHODS AND COMPOSITIONS FOR TREATING CELLULAR PROLIFERATIVE DISEASES
  申请人：THE MASSACHUSETTS INSTITUTE OF TECHNOLOGY

  公开号：EP1824498A2

  公开（公告）日：2007-08-29
• Methods and compositions for treating cellular proliferative diseases
  申请人：Yaffe B. Michael

  公开号：US20060115453A1

  公开（公告）日：2006-06-01

  The present invention relates to compounds and pharmaceutical compositions for treating cellular proliferative disorders, screening assays for identifying such compounds, and methods for treating such disorders.