5-methoxy-3-amino>-3,4-dihydro-2H-1-benzopyran | 155787-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-methoxy-3-amino>-3,4-dihydro-2H-1-benzopyran
• 英文别名: 5-METHOXY-3-{N-[4-(4,4-DIMETHYL-2,6-DIOXO-1-PIPERIDYL)BUTYL]AMINO}CHROMAN；5-METHOXY-3-{N-[4-(4,4-DIMETHYL-2,6-DIOXO1-PIPERIDYL)BUTYL]AMINO}CHROMAN；1-[4-[(5-methoxy-3,4-dihydro-2H-chromen-3-yl)amino]butyl]-4,4-dimethylpiperidine-2,6-dione
• CAS: 155787-19-2
• 化学式: C₂₁H₃₀N₂O₄
• 分子量: 374.48
• InChiKey: KQAAENLIAMRMSI-UHFFFAOYSA-N

物化性质

• 沸点：
  564.8±50.0 °C(predicted)
• 密度：
  1.17±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-碘代丙烷 、 5-methoxy-3-amino>-3,4-dihydro-2H-1-benzopyran 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以77%的产率得到5-methoxy-3-amino>-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  3,4-Dihydro-3-amino-2H-1-benzopyran Derivatives as 5-HT1A Receptor Ligands and Potential Anxiolytic Agents. 1. Synthesis and Structure-Activity Relationship Studies

  摘要：

  A series of 3,4-dihydro-3-amino-2H-1-benzopyran derivatives were prepared in order to determine the necessary structural requirements for good affinity for 5-HT1A receptors and high selectivity versus other receptors. Modifications of the extracyclic amino substituents, the length of the alkyl side chains, and their substituents were explored. The best compounds (9g, 9k, 15b, 15d) possess imido or sulfonamido functional groups with, a preferential length of four methylenes for the side chain. After resolution, the dextrorotatory enantiomers showed better affinity and selectivity for 5-HT1A receptors. These compounds have been proven to be full agonists. 9g and its enantiomers showed anxiolytic activity in vivo in various comportemental models. The compound (+)-9g is currently under clinical investigation.

  DOI：

  10.1021/jm00038a007
• 作为产物：
  描述：

  1-(4-溴丁基)-4,4-二甲基哌啶-2,6-二酮 以58%的产率得到5-methoxy-3-amino>-3,4-dihydro-2H-1-benzopyran
  参考文献：
  名称：

  3-aminochroman compounds

  摘要：

  该发明涉及以下式(I)的化合物：##STR1## 其中：Z代表氧，R.sub.1代表烷基，R.sub.2代表氢或烷基，n代表1到6，R.sub.3代表未取代或取代的苯基乙酰氨基，以及含有这些化合物的抗抑郁和其他药物制剂。

  公开号：

  US05510374A1

文献信息

• Alkoxy-3-[(Toluenesulfonylaminoalkyl)amino] chroman compounds
  申请人：Adir Et Compagnie

  公开号：US05346916A1

  公开（公告）日：1994-09-13

  The invention relates to compounds of the formula (I): ##STR1## in which: Z represents an oxygen atom or a sulfur atom, R.sub.1 represents a hydrogen atom or an alkyl group, R.sub.2 represents a hydrogen atom or an alkyl group, n is one to six, inclusive, R.sub.3 represents an amino group, substituted with phenylsulfonyl, and medicinal products containing the same.

  本发明涉及公式(I)的化合物：##STR1## 其中：Z代表氧原子或硫原子，R.sub.1代表氢原子或烷基，R.sub.2代表氢原子或烷基，n为1至6（包括1和6），R.sub.3代表取代苯磺酰氨基的氨基，以及含有这些化合物的药物产品。
• US5252578A
  申请人：——

  公开号：US5252578A

  公开（公告）日：1993-10-12
• US5314907A
  申请人：——

  公开号：US5314907A

  公开（公告）日：1994-05-24
• US5346916A
  申请人：——

  公开号：US5346916A

  公开（公告）日：1994-09-13
• 3,4-Dihydro-3-amino-2H-1-benzopyran Derivatives as 5-HT1A Receptor Ligands and Potential Anxiolytic Agents. 1. Synthesis and Structure-Activity Relationship Studies
  作者：Tchao Podona、Beatrice Guardiola-Lemaitre、Daniel-Henri Caignard、Gerard Adam、Bruno Pfeiffer、Pierre Renard、Gerald Guillaumet

  DOI：10.1021/jm00038a007

  日期：1994.6

  A series of 3,4-dihydro-3-amino-2H-1-benzopyran derivatives were prepared in order to determine the necessary structural requirements for good affinity for 5-HT1A receptors and high selectivity versus other receptors. Modifications of the extracyclic amino substituents, the length of the alkyl side chains, and their substituents were explored. The best compounds (9g, 9k, 15b, 15d) possess imido or sulfonamido functional groups with, a preferential length of four methylenes for the side chain. After resolution, the dextrorotatory enantiomers showed better affinity and selectivity for 5-HT1A receptors. These compounds have been proven to be full agonists. 9g and its enantiomers showed anxiolytic activity in vivo in various comportemental models. The compound (+)-9g is currently under clinical investigation.