6-(二甲基氨基)-3-吡啶醇 | 330473-71-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 6-(二甲基氨基)-3-吡啶醇
• 英文名称: 6-(dimethylamino) pyridin-3-ol
• 英文别名: 2-(dimethylamino)-4,6-dimethyl-5-pyrimidinol；Me2NPyr；DM-Pyr；6-N,N-dimethylamino-3-pyridinol；2-dimethylamino-5-hydroxypyridine；2-dimethylamino-5-pyridinol；6-(Dimethylamino)pyridin-3-OL
• CAS: 330473-71-7
• 化学式: C₇H₁₀N₂O
• 分子量: 138.169
• InChiKey: FEKGPMCJEOPIRR-UHFFFAOYSA-N

物化性质

• 沸点：
  347.7±27.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  6-(二甲基氨基)-3-吡啶醇 、 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 15.0h， 以32%的产率得到1-(3-((6-(dimethylamino)pyridin-3-yl)oxy)-2-hydroxy-2-methylpropanoyl)indoline-4-carbonitrile
  参考文献：
  名称：

  1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators

  摘要：

  We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.

  DOI：

  10.1021/jm401625b
• 作为产物：
  描述：

  2-氯-5-羟基吡啶 在 tris-(dibenzylideneacetone)dipalladium(0) 、 氢溴酸 、 sodium methylate 、 sodium hydride 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 溶剂黄146 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 39.5h， 生成 6-(二甲基氨基)-3-吡啶醇
  参考文献：
  名称：

  1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile Derivatives as Potent and Tissue Selective Androgen Receptor Modulators

  摘要：

  We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.

  DOI：

  10.1021/jm401625b

文献信息

• INHIBITORS OF HEMEPROTEIN-CATALYZED LIPID PEROXIDATION
  申请人：VANDERBILT UNIVERSITY

  公开号：US20150368241A1

  公开（公告）日：2015-12-24

  Compounds, compositions and methods related to the prevention or treatment of isoprostane-mediated tissue damage in a mammalian subject in need thereof.

  与哺乳动物受体内异前列腺素介导的组织损伤的预防或治疗相关的化合物、组合物和方法。
• Inhibitors of hemeprotein-catalyzed lipid peroxidation
  申请人：Vanderbilt University

  公开号：US10675285B2

  公开（公告）日：2020-06-09

  Methods and compounds for the treatment or prevention of oxidative damage in a mammalian subject. The treatment and/or prevention may be on inhibiting heme-induced lipid peroxidation. Also discloses are methods and compounds for treating or preventing isoprostane-mediated tissue damage.

  用于治疗或预防哺乳动物体内氧化损伤的方法和化合物。 这种治疗和/或预防可以是抑制血红素诱导的脂质过氧化。 还公开了用于治疗或预防异丙烷介导的组织损伤的方法和化合物。
• Method for preventing hemoprotein and heme-mediated lipid peroxidation
  申请人：Oates A. John

  公开号：US20060009496A1

  公开（公告）日：2006-01-12

  The invention provides a method for inhibiting hemoprotein- and heme-induced lipid peroxidation, a method for identifying compositions that are effective to inhibit hemoprotein- or heme-induced lipid peroxidation, and methods of therapeutic use for those compounds.

  本发明提供了一种抑制血蛋白和血红素诱导的脂质过氧化反应的方法、一种鉴别有效抑制血蛋白或血红素诱导的脂质过氧化反应的组合物的方法，以及这些化合物的治疗使用方法。
• A Simple Cu-Catalyzed Coupling Approach to Substituted 3-Pyridinol and 5-Pyrimidinol Antioxidants
  作者：Susheel J. Nara、Mukund Jha、Johan Brinkhorst、Tony J. Zemanek、Derek A. Pratt

  DOI：10.1021/jo801501e

  日期：2008.12.5

  A convenient approach to 3-pyridinols and 5-pyrimidinols via a two-step Cu-catalyzed benzyloxylation/catalytic hydrogenation sequence is presented. The corresponding 3-pyridinamines and 5-pyrimidinamines can be prepared in an analogous sequence utilizing benzylamine in lieu of benzyl alcohol. The radical-scavenging ability of these derivatives are preliminarily explored and reveal that the increased acidities of the pyridinols and pyrimidinols render them susceptible to more significant kinetic solvent effects when compared to phenols.
• Inhibitors of Hemeprotein-Catalyzed Lipid Peroxidation
  申请人：Vanderbilt University

  公开号：US20160067256A1

  公开（公告）日：2016-03-10

  Methods and compounds for the treatment or prevention of oxidative damage in a mammalian subject. The treatment and/or prevention may be on inhibiting heme-induced lipid peroxidation. Also discloses are methods and compounds for treating or preventing isoprostane-mediated tissue damage.