6-溴-1-甲氧基异喹啉 | 891785-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 6-溴-1-甲氧基异喹啉
• 英文名称: 6-bromo-1-methoxyisoquinoline
• 英文别名: 1-Methoxy-6-bromoisoquinoline
• CAS: 891785-23-2
• 化学式: C₁₀H₈BrNO
• 分子量: 238.084
• InChiKey: ZXSUFWUXOVNEER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-溴-1-甲氧基异喹啉 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-{5-[(2S)-2-amino-3-(1H-indol-3-yl)propoxy]pyridin-3-yl}-1-methoxyisoquinoline
  参考文献：
  名称：

  Isoquinoline–pyridine-based protein kinase B/Akt antagonists: SAR and in vivo antitumor activity

  摘要：

  The structure-activity relationships of a series of isoquinoline-pyridine-based protein kinase B/Akt antagonists have been investigated in an effort to improve the major short-comings of the lead compound 3, including poor pharmacokinetic profiles in several species (e.g., mouse iv t(1/2) = 0.3 h, po F= 0%). Chlorination at C-1 position of the isoquinoline improved its pharmacokinetic property in mice (iv t(1/2) = 5.0 h, po F = 51%) but resulted in > 500-fold drop in potency. In a mouse MiaPaCa-2 xenograft model, an amino analog 10y significantly slowed the tumor growth, however was accompanied by toxicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.041
• 作为产物：
  描述：

  甲醇 、 6-溴-2H-异喹啉-1-酮 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到6-溴-1-甲氧基异喹啉
  参考文献：
  名称：

  Isoquinoline–pyridine-based protein kinase B/Akt antagonists: SAR and in vivo antitumor activity

  摘要：

  The structure-activity relationships of a series of isoquinoline-pyridine-based protein kinase B/Akt antagonists have been investigated in an effort to improve the major short-comings of the lead compound 3, including poor pharmacokinetic profiles in several species (e.g., mouse iv t(1/2) = 0.3 h, po F= 0%). Chlorination at C-1 position of the isoquinoline improved its pharmacokinetic property in mice (iv t(1/2) = 5.0 h, po F = 51%) but resulted in > 500-fold drop in potency. In a mouse MiaPaCa-2 xenograft model, an amino analog 10y significantly slowed the tumor growth, however was accompanied by toxicity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.03.041

文献信息

• [EN] 1, 4-SUBSTITUTED PIPERIDINE DERIVATIVES<br/>[FR] DÉRIVÉS DE PIPÉRIDINE 1,4-SUBSTITUÉS
  申请人：CEPHALON INC

  公开号：WO2016205633A1

  公开（公告）日：2016-12-22

  Described herein are 1,4-substituted piperidine compounds according to Formula (I) that have demonstrated activity as fatty acid synthase inhibitors. Also described herein are pharmaceutical compositions containing the described 1,4-substituted piperidine compounds, and methods of treating diseases mediated by fatty acid synthase, by administering one or more of the compounds or pharmaceutical formulations described herein. Also described herein are methods of synthesizing the compounds described, including the described 1,4-substituted piperidine compounds and synthetic intermediates useful in those syntheses.

  本文描述了按照式（I）的1,4-取代哌啶化合物，这些化合物已经表现出作为脂肪酸合成酶抑制剂的活性。本文还描述了含有所述1,4-取代哌啶化合物的药物组合物，以及通过给予所述化合物或药物配方中的一个或多个来治疗由脂肪酸合成酶介导的疾病的方法。本文还描述了合成所述化合物的方法，包括所述的1,4-取代哌啶化合物和在这些合成中有用的合成中间体。
• [EN] PIPERAZINE DERIVATIVE, PREPARATION METHOD THEREFOR AND USE THEREOF<br/>[FR] DÉRIVÉ DE PIPÉRAZINE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 哌嗪类衍生物及其制备方法和用途
  申请人：ZHEJIANG HISUN PHARM CO LTD

  公开号：WO2022057849A1

  公开（公告）日：2022-03-24

  本发明涉及哌嗪类衍生物、其制备方法及其在医药上的应用。具体而言，本发明涉及一种通式(I)所示的哌嗪类衍生物、其制备方法及其可药用的盐，或其前药，以及它们作为治疗剂、特别是作为凝血因子XIa(FXIa)抑制剂的用途，其中通式(I)中的各取代基的定义与说明书中的定义相同，
• [EN] PYRIDINE QUINOLINE COMPOUNDS AS MGLUR4 ALLOSTERIC POTENTIATORS, COMPOSITIONS, AND METHODS OF TREATING NEUROLOGICAL DYSFUNCTION<br/>[FR] COMPOSÉS DE QUINOLÉINES PYRIDINE UTILISÉS EN TANT QUE POTENTIALISATEURS ALLOSTÉRIQUES DE MGLUR4, COMPOSITIONS, ET MÉTHODES DE TRAITEMENT DE DYSFONCTIONNEMENTS NEUROLOGIQUES
  申请人：UNIV VANDERBILT

  公开号：WO2019006157A1

  公开（公告）日：2019-01-03

  Pyridine quinoline compounds which are useful as allosteric potentiators/positive allosteric modulators of the metabotropic glutamate receptor subtype 4 (mGluR4); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds, for example, in treating neurological and psychiatric disorders or other disease states associated with glutamate dysfunction.

  吡啶喹啉化合物可用作代谢型谷氨酸受体亚型4（mGluR4）的变构增强剂/正向变构调节剂；制备这些化合物的合成方法；含有这些化合物的药物组合物；以及使用这些化合物的方法，例如用于治疗神经和精神障碍或其他与谷氨酸功能异常相关的疾病状态。
• [EN] C-LINKED INHIBITORS OF ENL/AF9 YEATS<br/>[FR] INHIBITEURS À LIAISON C D'AMPLIFICATEURS DE YEATS ENL/AF9
  申请人：BRIDGE MEDICINES

  公开号：WO2022240830A1

  公开（公告）日：2022-11-17

  Compounds of Formula I and pharmaceutical compositions comprising compounds of Formula I are disclosed. Methods for treating acute leukemias using the compounds of Formula I and pharmaceutical compositions comprising the same are also disclosed.

  本发明揭示了式I化合物和包含式I化合物的制药组合物。本发明还揭示了使用式I化合物和包含其的制药组合物治疗急性白血病的方法。
• Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate
  作者：Ayumi Inami、Yuji Nishii、Koji Hirano、Masahiro Miura

  DOI：10.1021/acs.orglett.3c00826

  日期：2023.5.12

  promising synthetic method; however, catalytic synthesis of 3,4-nonsubstituted isoquinolines by formal acetylene annulation has been scarce to date. Herein, we introduce vinyl selenone as an effective acetylene surrogate for the Rh-catalyzed annulative coupling under mild conditions. The Se fragment can be recovered as diselenide and recycled. The product can readily be converted to 1-aminoisoquinolines

  异喹啉是许多生物活性化合物和有价值的配体中的特殊结构。过渡金属催化氧化环化亚胺衍生物已成为一种很有前途的合成方法；然而，迄今为止，通过形式乙炔环化催化合成 3,4-未取代的异喹啉一直很少。在此，我们介绍了乙烯基硒酮作为一种有效的乙炔替代物，用于温和条件下 Rh 催化的环状偶联。Se片段可以作为二硒化物回收并循环使用。该产品可以很容易地转化为 1-氨基异喹啉。