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5-溴-N,N,4,6-四甲基吡啶-2-胺 | 627098-10-6

中文名称
5-溴-N,N,4,6-四甲基吡啶-2-胺
中文别名
——
英文名称
5-bromo-4,6-dimethyl-2-(dimethylamino)pyridine
英文别名
2-N,N-dimethylamino-5-bromo-4,6-dimethylpyridine;5-Bromo-N,N,4,6-tetramethylpyridin-2-amine
5-溴-N,N,4,6-四甲基吡啶-2-胺化学式
CAS
627098-10-6
化学式
C9H13BrN2
mdl
——
分子量
229.12
InChiKey
CISMTWZQYSPXPU-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.8
  • 重原子数:
    12
  • 可旋转键数:
    1
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.44
  • 拓扑面积:
    16.1
  • 氢给体数:
    0
  • 氢受体数:
    2

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Design of 2,5-Dimethyl-3-(6-dimethyl-4-methylpyridin-3-yl)-7-dipropylaminopyrazolo[1,5-a]pyrimidine (NBI 30775/R121919) and Structure−Activity Relationships of a Series of Potent and Orally Active Corticotropin-Releasing Factor Receptor Antagonists
    摘要:
    We have previously shown that 3-phenylpyrazolo[1,5-a]pyrimidines exemplified by 8 were potent antagonists of the human corticotropin-releasing factor-1 receptor. A series of 3-pyridylpyrazolo[1,5-a]pyrimidines 15, 25-30, 34, and 35 containing a weakly basic pyridine ring at the 3-position of the bicyclic nucleus was designed to reduce lipophilicity from the initial leads such as 7. Here, we showed that these 3-pyridyl compounds exhibited potent antagonists at the human CRF1, receptor. Moreover, the hydrophilic and weakly basic pyridine moiety increased the water solubility of some analogues. Compound 26h exhibited good binding affinity at the human CRF1 receptor with a K-i value of 3.5 nM. As a functional antagonist, it dose-dependently inhibited CRF-stimulated cAMP production in cells expressing the CRF1 receptor [IC50 = 50 nM), and CRF-stimulated ACTH release from cultured rat pituitary cells [IC50 = 20 nM). 26h had a log P value of 4.9 and water solubility of greater than 10 mg/mL. Pharmacokinetic studies in rats showed that 26h was orally bioavailable and able to penetrate into the brain. 26h has been demonstrated in vivo efficacy in animal behavioral models that measure anxiolytic activity. These results suggest that analogues from this series were potent CRF1, receptor antagonists with proper physicochemical properties and good pharmacokinetic profiles. 26h was developed into a clinical compound and exhibited efficacy in patients with major depression.
    DOI:
    10.1021/jm040058e
  • 作为产物:
    描述:
    2-dimethylamino-4,6-dimethylpyridine 在 disodium hydrogenphosphate 作用下, 以 为溶剂, 反应 4.25h, 生成 5-溴-N,N,4,6-四甲基吡啶-2-胺
    参考文献:
    名称:
    Synthesis and Structure−Activity Relationships of 8-(Pyrid-3-yl)pyrazolo[1,5-a]-1,3,5-triazines: Potent, Orally Bioavailable Corticotropin Releasing Factor Receptor-1 (CRF1) Antagonists
    摘要:
    This report describes the syntheses and structure-activity relationships of 8-(substituted pyridyl)pyrazolo[1,5-a]-1,3,5-triazine corticotropin releasing factor receptor-1 (CRF1) receptor antagonists. These CRF1 receptor antagonists may be potential anxiolytic or antidepressant drugs. This research resulted in the discovery of compound 13-15, which is a potent, selective CRF1 antagonist (hCRF(1) IC50 = 6.1 +/- 0.6 nM) with weak affinity for the CRF-binding protein and biogenic amine receptors. This compound also has a good pharmacokinetic profile in dogs. Analogue 13-15 is orally effective in two rat models of anxiety: the defensive withdrawal (situational anxiety) model and the elevated plus maze test. Analogue 13-15 has been advanced to clinical trials.
    DOI:
    10.1021/jm900025h
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文献信息

  • [EN] MULTIFUNCTIONAL RADICAL QUENCHERS AND THEIR USE<br/>[FR] DÉSACTIVATEURS DE RADICAUX LIBRES MULTIFONCTIONNELS ET LEUR UTILISATION
    申请人:UNIV ARIZONA
    公开号:WO2011103536A1
    公开(公告)日:2011-08-25
    The present disclosure provides biologically active compounds of formula (I): and pharmaceutically acceptable salts thereof, compositions comprising these compounds, and methods of using these compounds in a variety of applications, such as treatment or suppression of diseases associated with decreased mitochondrial function resulting in diminished ATP production and/or oxidative stress and/or lipid peroxidation.
    本公开提供了具有生物活性的公式(I)化合物:以及它们的药用可接受盐,包含这些化合物的组合物,以及在这些化合物在各种应用中的使用方法,例如治疗或抑制与线粒体功能降低有关的疾病,导致ATP产生减少和/或氧化应激和/或脂质过氧化。
  • A general and efficient method for the synthesis of benzo-(iso)quinoline derivatives
    作者:Victor Mamane、Frédéric Louërat、Julien Iehl、Mohamed Abboud、Yves Fort
    DOI:10.1016/j.tet.2008.09.015
    日期:2008.11
    short and efficient synthesis of substituted benzo-(iso)quinoline derivatives is reported. The methodology is based on a Suzuki or Negishi cross-coupling followed by a cyclization reaction induced by t-BuOK in DMF to form the central ring. This approach allowed the synthesis of all four benzo-(iso)quinoline isomers and the substitution of each ring of the benzo-(iso)quinoline core.
    报道了一种新的,短而有效的取代苯并-(异)喹啉衍生物的合成方法。该方法基于Suzuki或Negishi交叉偶联,然后是在DMF中由t -BuOK诱导形成中心环的环化反应。这种方法可以合成所有四种苯并(异)喹啉异构体,并取代苯并(异)喹啉核心的每个环。
  • Synthesis and Reactivity of Some 6-Substituted-2,4-dimethyl-3-pyridinols, a Novel Class of Chain-Breaking Antioxidants
    作者:Maikel Wijtmans、Derek A. Pratt、Johan Brinkhorst、Remigiusz Serwa、Luca Valgimigli、Gian Franco Pedulli、Ned A. Porter
    DOI:10.1021/jo048842u
    日期:2004.12.1
    found to be indefinitely stable to air oxidation while 2 and 3 decomposed upon extended exposure to the atmosphere. The reactivities of the pyridinols toward chain-carrying peroxyl radicals in homogeneous organic solution were examined by studying the kinetics of radical-initiated styrene autoxidations under controlled conditions. These experiments revealed that some of the newly synthesized pyridinols
    报道了一系列具有令人感兴趣的抗氧化剂性质的6-取代的2,4-二甲基-3-吡啶基醇的合成和研究。导致化合物的一般合成策略是将低温芳基溴化物转化为酒精,这是最后一步。由此制备了2,4-二甲基-3-吡啶醇(1a),2,4,6-三甲基-3-吡啶醇(1b)和2,4-二甲基-6-(二甲基氨基)-3-吡啶醇(1d)。得自相应的3-溴吡啶前体。甲氧基衍生物2,4-二甲基-6-(甲氧基)-3-吡啶醇(1c)也通过替代路线,通过Baeyer-Villiger反应在取代的苯甲醛前体上制备。新型双环吡啶并2和3需要事先构造环形结构。因此,2是通过6步分子内Friedel-Crafts策略制备的,3则需要11步序列,嘧啶环和炔烃之间的热解分子内反需求Diels-Alder反应是关键步骤。吡啶醇的碱性随着环中电子密度的增加而接近生理pH。发现吡啶酮1a - d对空气氧化具有无限的稳定性,而2和3长时间暴露在大气中会分
  • Multifunctional Radical Quenchers and Their Uses
    申请人:HECHT Sidney
    公开号:US20130267546A1
    公开(公告)日:2013-10-10
    The present disclosure provides biologically active compounds of formula (I): and pharmaceutically acceptable salts thereof: compositions comprising these compounds, and methods of using these compounds in a variety of applications, such as treatment or suppression of diseases associated with decreased mitochondrial function resulting in diminished ATP production and/or oxidative stress and/or lipid peroxidation.
    本公开提供了式(I)的生物活性化合物及其药学上可接受的盐:包含这些化合物的组合物,以及使用这些化合物在多种应用中的方法,例如治疗或抑制与减少线粒体功能相关的疾病,导致ATP产生减少和/或氧化应激和/或脂质过氧化。
  • 6-Amino-3-Pyridinols: Towards Diffusion-Controlled Chain-Breaking Antioxidants
    作者:Maikel Wijtmans、Derek A. Pratt、Luca Valgimigli、Gino A. DiLabio、Gian Franco Pedulli、Ned A. Porter
    DOI:10.1002/anie.200351881
    日期:2003.9.22
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