trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2-b><1,4>oxazine | 92422-25-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2-b><1,4>oxazine
• 英文别名: trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2b><1,4>oxazine；trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2-b][1,4]oxazine；trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth[1,2b][1,4]oxazine；rel-(4aS,10bS)-9-methoxy-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine；(4aS,10bS)-9-methoxy-3,4,4a,5,6,10b-hexahydro-2H-benzo[h][1,4]benzoxazine
• CAS: 92422-25-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: ZBQMPCXNGKZCPK-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2-b><1,4>oxazine 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 trans-N-n-propyl-9-hydroxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2b><1,4>oxazine
  参考文献：
  名称：

  Dykstra; Hazelhoff; Mulder, European Journal of Medicinal Chemistry, 1985, vol. 20, # 3, p. 247 - 250

  摘要：

  DOI：
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 在 palladium on activated charcoal sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 氢气 、 sodium hydride 、 sodium carbonate 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 甲醚 、 乙二醇 、 正丁醇 为溶剂， 反应 8.0h， 生成 trans-9-methoxy-2,3,4a,5,6,10b-hexahydro-4H-naphth<1,2-b><1,4>oxazine
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014

文献信息

• Further Characterization of Structural Requirements for Ligands at the Dopamine D₂ and D₃ Receptor:  Exploring the Thiophene Moiety
  作者：Durk Dijkstra、Nienke Rodenhuis、Erik S. Vermeulen、Thomas A. Pugsley、Lawrence D. Wise、Håkan V. Wikström

  DOI：10.1021/jm001015a

  日期：2002.7.1

  The present study describes the synthesis and in vitro pharmacology of a novel series of dopaminergic agents in which the classical phenylethylamine pharmacophore is replaced by a thienylethylamine moiety. In general, the novel compounds showed a moderate affinity for the dopamine (DA) D-2 and D-3 receptors. When the thienylethylamine moiety is fixed in a rigid system, the affinity for the DA receptor is significantly increased. However, in the tricyclic hexahydrothianaphthoxazine structure, the affinity for the DA receptors is diminished.
• Perrone; Berardi; Bettoni, Farmaco, Edizione Scientifica, 1985, vol. 40, # 6, p. 422 - 428
  作者：Perrone、Berardi、Bettoni、Tortorella

  DOI：——

  日期：——
• Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists
  作者：James H. Jones、Paul S. Anderson、John J. Baldwin、Bradley V. Clineschmidt、David E. McClure、George F. Lundell、William C. Randall、Gregory E. Martin、Michael Williams

  DOI：10.1021/jm00378a014

  日期：1984.12

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.
• Dykstra; Hazelhoff; Mulder, European Journal of Medicinal Chemistry, 1985, vol. 20, # 3, p. 247 - 250
  作者：Dykstra、Hazelhoff、Mulder、et al.

  DOI：——

  日期：——