2-甲基-7-硝基-3,4-二氢-2H-1,4-苯并恶嗪 | 941291-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 2-甲基-7-硝基-3,4-二氢-2H-1,4-苯并恶嗪
• 英文名称: (+/-)-3,4-dihydro-2-methyl-7-nitro-2H-1,4-benzoxazine
• 英文别名: 2-methyl-7-nitro-3,4-dihydro-2H-1,4-benzoxazine
• CAS: 941291-25-4
• 化学式: C₉H₁₀N₂O₃
• 分子量: 194.19
• InChiKey: XGQMNDZPLBYYTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-7-硝基-3,4-二氢-2H-1,4-苯并恶嗪 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (+/-)-7-amino-3,4-dihydro-2,4-dimethyl-2H-1,4-benzoxazine
  参考文献：
  名称：

  Novel Series of Potent, Nonsteroidal, Selective Androgen Receptor Modulators Based on 7H-[1,4]Oxazino[3,2-g]quinolin-7-ones

  摘要：

  Recent interest in orally available androgens has fueled the search for new androgens for use in hormone replacement therapy and as anabolic agents. In pursuit of this, we have discovered a series of novel androgen receptor modulators derived from 7H-[1,4]oxazino[3,2-g]quinolin-7-ones. These compounds were synthesized and evaluated in competitive binding assays and an androgen receptor transcriptional activation assay. A number of compounds from the series demonstrated single-digit nanomolar agonist activity in vitro. In addition, lead compound (R)-16e was orally active in established rodent models that measure androgenic and anabolic properties of these agents. In this assay, (R)-16e demonstrated full efficacy in muscle and only partially stimulated the prostate at 100 mg/kg. These data suggest that these compounds may be utilized as selective androgen receptor modulators or SARMs. This series represents a novel class of compounds for use in androgen replacement therapy.

  DOI：

  10.1021/jm061329j
• 作为产物：
  描述：

  2-氨基-5-硝基苯酚 在 dimethyl sulfide borane 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-甲基-7-硝基-3,4-二氢-2H-1,4-苯并恶嗪
  参考文献：
  名称：

  Novel Series of Potent, Nonsteroidal, Selective Androgen Receptor Modulators Based on 7H-[1,4]Oxazino[3,2-g]quinolin-7-ones

  摘要：

  Recent interest in orally available androgens has fueled the search for new androgens for use in hormone replacement therapy and as anabolic agents. In pursuit of this, we have discovered a series of novel androgen receptor modulators derived from 7H-[1,4]oxazino[3,2-g]quinolin-7-ones. These compounds were synthesized and evaluated in competitive binding assays and an androgen receptor transcriptional activation assay. A number of compounds from the series demonstrated single-digit nanomolar agonist activity in vitro. In addition, lead compound (R)-16e was orally active in established rodent models that measure androgenic and anabolic properties of these agents. In this assay, (R)-16e demonstrated full efficacy in muscle and only partially stimulated the prostate at 100 mg/kg. These data suggest that these compounds may be utilized as selective androgen receptor modulators or SARMs. This series represents a novel class of compounds for use in androgen replacement therapy.

  DOI：

  10.1021/jm061329j

文献信息

• Androgen receptor modulator compounds and methods
  申请人：Ligand Pharmaceuticals, Inc.

  公开号：US06462038B1

  公开（公告）日：2002-10-08

  Compounds, pharmaceutical compositions, and methods for modulating processes mediated by steroid receptors. In particular, preparation and methods of use of non-steroidal compounds and compositions that are agonists, partial agonists, and antagonists for the androgen receptor (AR) are described. Further, described are the methods of making and use of critical intermediates including a stereoselective synthetic route to intermediates for the AR modulators.

  化合物、药物组合物和调节类固醇受体介导过程的方法。具体描述了非类固醇化合物和组合物的制备和使用方法，这些化合物和组合物是雄激素受体（AR）的激动剂、部分激动剂和拮抗剂。此外，还描述了制备和使用关键中间体的方法，包括用于AR调节剂的立体选择性合成路线。
• [EN] ANDROGEN RECEPTOR MODULATOR COMPOUNDS AND METHODS<br/>[FR] COMPOSES DE MODULATION DU RECEPTEUR ANDROGENE ET PROCEDES D'UTILISATION
  申请人：LIGAND PHARM INC

  公开号：WO2001016139A1

  公开（公告）日：2001-03-08

  Compounds, pharmaceutical compositions, and methods for modulating processes mediated by steroid receptors. In particular, preparation and methods of use of non-steroidal compounds and compositions that are agonists, partial agonists, and antagonists for the androgen receptor (AR) are described. Further, described are the methods of making and use of critical intermediates including a stereoselective synthetic route to intermediates for the AR modulators.

  化合物、药物组合物和调节类固醇受体介导过程的方法。特别地，描述了非类固醇化合物和组合物的制备和使用方法，这些化合物和组合物是雄激素受体（AR）的激动剂、部分激动剂和拮抗剂。此外，还描述了制备和使用关键中间体的方法，包括用于AR调节剂的立体选择性合成路线的中间体。
• ANDROGEN RECEPTOR MODULATOR COMPOUNDS AND METHODS
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：EP1212330B1

  公开（公告）日：2006-04-19
• US6462038B1
  申请人：——

  公开号：US6462038B1

  公开（公告）日：2002-10-08
• Novel Series of Potent, Nonsteroidal, Selective Androgen Receptor Modulators Based on 7<i>H</i>-[1,4]Oxazino[3,2-<i>g</i>]quinolin-7-ones
  作者：Robert I. Higuchi、Kristen L. Arienti、Francisco J. López、Neelakhanda S. Mani、Dale E. Mais、Thomas R. Caferro、Yun Oliver Long、Todd K. Jones、James P. Edwards、Lin Zhi、William T. Schrader、Andrés Negro-Vilar、Keith B. Marschke

  DOI：10.1021/jm061329j

  日期：2007.5.1

  Recent interest in orally available androgens has fueled the search for new androgens for use in hormone replacement therapy and as anabolic agents. In pursuit of this, we have discovered a series of novel androgen receptor modulators derived from 7H-[1,4]oxazino[3,2-g]quinolin-7-ones. These compounds were synthesized and evaluated in competitive binding assays and an androgen receptor transcriptional activation assay. A number of compounds from the series demonstrated single-digit nanomolar agonist activity in vitro. In addition, lead compound (R)-16e was orally active in established rodent models that measure androgenic and anabolic properties of these agents. In this assay, (R)-16e demonstrated full efficacy in muscle and only partially stimulated the prostate at 100 mg/kg. These data suggest that these compounds may be utilized as selective androgen receptor modulators or SARMs. This series represents a novel class of compounds for use in androgen replacement therapy.