(+/-)-2,3-dihydro-2-(hydroxymethyl)-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline | 329229-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+/-)-2,3-dihydro-2-(hydroxymethyl)-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline
• 英文别名: [7-propan-2-yloxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-2,3-dihydropyrido[3,2-g][1,4]benzoxazin-2-yl]methanol
• CAS: 329229-45-0
• 化学式: C₁₈H₁₈F₆N₂O₃
• 分子量: 424.343
• InChiKey: KCOKNBZZXWUMIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.8
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (+/-)-2,3-dihydro-2-(hydroxymethyl)-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline 生成
  参考文献：
  名称：

  Selective androgen receptor modulators based on a series of 7H-[1,4]oxazino[3,2-g]quinolin-7-ones with improved in vivo activity

  摘要：

  Modification on a lead series of [1,4] oxazino[3,2-g] quinolin-7-ones at the 2-position led to selective androgen receptor modulators with improved in vivo activity. The most potent analog (-)-33a exhibited full maintenance of levator ani muscle at 3 mg/kg and reduced activity on ventral prostate weight in a 2-week orally-dosed and orchidectomized rat maintenance assay. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.062
• 作为产物：
  描述：

  (+/-)-2,3-dihydro-7-isopropoxy-2-methylene-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline 在 sodium hydroxide 、 硼烷 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 生成 (+/-)-2,3-dihydro-2-(hydroxymethyl)-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline
  参考文献：
  名称：

  Selective androgen receptor modulators based on a series of 7H-[1,4]oxazino[3,2-g]quinolin-7-ones with improved in vivo activity

  摘要：

  Modification on a lead series of [1,4] oxazino[3,2-g] quinolin-7-ones at the 2-position led to selective androgen receptor modulators with improved in vivo activity. The most potent analog (-)-33a exhibited full maintenance of levator ani muscle at 3 mg/kg and reduced activity on ventral prostate weight in a 2-week orally-dosed and orchidectomized rat maintenance assay. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.062

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
• Selective androgen receptor modulators based on a series of 7H-[1,4]oxazino[3,2-g]quinolin-7-ones with improved in vivo activity
  作者：Yun Oliver Long、Robert I. Higuchi、Thomas R. Caferro、Thomas L.S. Lau、Min Wu、Marquis L. Cummings、Esther A. Martinborough、Keith B. Marschke、William Y. Chang、Francisco J. López、Donald S. Karanewsky、Lin Zhi

  DOI：10.1016/j.bmcl.2008.03.062

  日期：2008.5

  Modification on a lead series of [1,4] oxazino[3,2-g] quinolin-7-ones at the 2-position led to selective androgen receptor modulators with improved in vivo activity. The most potent analog (-)-33a exhibited full maintenance of levator ani muscle at 3 mg/kg and reduced activity on ventral prostate weight in a 2-week orally-dosed and orchidectomized rat maintenance assay. (C) 2008 Elsevier Ltd. All rights reserved.