(2R,4aR,10aR)-9-methoxy-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine | 1202361-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2R,4aR,10aR)-9-methoxy-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine
• 英文别名: (2R,4aR,10aR)-9-methoxy-2-methylsulfanylmethyl-4-n-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine；(2R,4aR,10aR)-9-methoxy-2-methylsulfanylmethyl-4-n-propyl-3,4,4a,5,10,10a-hexalydro-2H-naphtho[2,3-b][1,4]oxazine；(2R,4aR,10aR)-9-methoxy-2-(methylsulfanylmethyl)-4-propyl-2,3,4a,5,10,10a-hexahydrobenzo[g][1,4]benzoxazine
• CAS: 1202361-65-6
• 化学式: C₁₈H₂₇NO₂S
• 分子量: 321.484
• InChiKey: JVBBVFKGGHELKD-QGPMSJSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4aR,10aR)-9-methoxy-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine 在 potassium fluoride 、 苯硫酚 、 盐酸 作用下， 以 N,N-二甲基乙酰胺 、 甲醇 、 乙醚 为溶剂， 反应 1.0h， 以14 mg的产率得到(2R,4aR,10aR)-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazin-9-ol hydrochloride
  参考文献：
  名称：

  Synthesis and SAR study of a novel series of dopamine receptor agonists

  摘要：

  The synthesis of a novel series of dopamine receptor agonists are described as well as their in vitro potency and efficacy on dopamine D-1 and D-2 receptors. This series was designed from pergolide and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g] quinolin-6-ol (PHBQ) and resulted in the synthesis of (2R,4aR,10aR)-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazin-9-ol (compound 27), which has a D-1 and D-2 receptor profile similar to that of the most recently approved drug for Parkinson's disease, rotigotine. (C)2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.012
• 作为产物：
  描述：

  5-甲氧基-1,4-二氢萘 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 sodium azide 、 18-冠醚-6 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 、 二乙胺 、 N,N-二甲基甲酰胺 为溶剂， 20.0~130.0 ℃ 、250.0 kPa 条件下， 反应 35.16h， 生成 (2R,4aR,10aR)-9-methoxy-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazine
  参考文献：
  名称：

  Synthesis and SAR study of a novel series of dopamine receptor agonists

  摘要：

  The synthesis of a novel series of dopamine receptor agonists are described as well as their in vitro potency and efficacy on dopamine D-1 and D-2 receptors. This series was designed from pergolide and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g] quinolin-6-ol (PHBQ) and resulted in the synthesis of (2R,4aR,10aR)-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazin-9-ol (compound 27), which has a D-1 and D-2 receptor profile similar to that of the most recently approved drug for Parkinson's disease, rotigotine. (C)2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.012

文献信息

• [EN] NOVEL PHENOLIC AND CATECHOLIC AMINES AND PRODRUGS THEREOF<br/>[FR] NOUVELLES AMINES PHÉNOLIQUES ET CATÉCHOLIQUES ET LEURS PROMÉDICAMENTS
  申请人：LUNDBECK & CO AS H

  公开号：WO2009156458A1

  公开（公告）日：2009-12-30

  The present invention relates to novel phenolic and catecholic amines of Formula 1, to processes for their preparation, pharmaceutical compositions containing them, to their use in therapy and to their use in radiolabeled form as PET- or SPECT Iigands.

  本发明涉及一种新型酚和儿茶酚胺，其化学式为1，以及它们的制备方法、含有它们的药物组合物，它们在治疗中的应用，以及它们以正电子发射断层扫描（PET）或单光子发射计算机断层扫描（SPECT）配体形式的应用。
• NOVEL PHENOLIC AND CATECHOLIC AMINES AND PRODRUGS THEREOF
  申请人：PUSCHL Ask

  公开号：US20090325946A1

  公开（公告）日：2009-12-31

  The present invention relates to novel phenolic and catecholic amines of Formula I, to processes for their preparation, pharmaceutical compositions containing them, to their use in therapy and to their use in radiolabeled form as PET- or SPECT ligands.

  本发明涉及一种新型的具有化学式I的酚胺和儿茶酚胺，以及它们的制备方法、含有它们的药物组合物、在治疗中的应用以及作为PET或SPECT配体的放射标记形式的应用。
• US8067410B2
  申请人：——

  公开号：US8067410B2

  公开（公告）日：2011-11-29
• Synthesis and SAR study of a novel series of dopamine receptor agonists
  作者：Rune Risgaard、Martin Jensen、Morten Jørgensen、Benny Bang-Andersen、Claus T. Christoffersen、Klaus G. Jensen、Jesper L. Kristensen、Ask Püschl

  DOI：10.1016/j.bmc.2013.11.012

  日期：2014.1

  The synthesis of a novel series of dopamine receptor agonists are described as well as their in vitro potency and efficacy on dopamine D-1 and D-2 receptors. This series was designed from pergolide and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g] quinolin-6-ol (PHBQ) and resulted in the synthesis of (2R,4aR,10aR)-2-methylsulfanylmethyl-4-propyl-3,4,4a,5,10,10a-hexahydro-2H-naphtho[2,3-b][1,4]oxazin-9-ol (compound 27), which has a D-1 and D-2 receptor profile similar to that of the most recently approved drug for Parkinson's disease, rotigotine. (C)2013 Elsevier Ltd. All rights reserved.