5-methoxy-3,4-dihydro-3--2H-1-benzopyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-methoxy-3,4-dihydro-3--2H-1-benzopyran
• 英文别名: 3-[N-PROPYL-N-(4-PHTHALIMIDOBUTYL)AMINO]-5-METHOXYCHROMAN；2-[4-[(5-methoxy-3,4-dihydro-2H-chromen-3-yl)-propylamino]butyl]isoindole-1,3-dione
• 化学式: C₂₅H₃₀N₂O₄
• 分子量: 422.524
• InChiKey: ISIUTFCGQWDGHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methoxy-3,4-dihydro-3--2H-1-benzopyran 、 3-[4-[N-(5-Methoxychroman-3-Yl)Amino]Butyl]-2,4-Dioxo-3-Azabicyclo[3.3.0]Octane 生成 3-{4-[N-PROPYL-N-(5-METHOXY-3-CHROMANYL)AMINO]-BUTYL}-2,4-DIOXO-3-AZABICYCLO[3.3.0]OCTANE
  参考文献：
  名称：

  3-aminochroman compounds

  摘要：

  本发明涉及一般式(I)的衍生物：##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，1≤n≤6，R.sub.3代表腈基、可选取代的氨基或描述中的任意一种基团，以及药物制剂。

  公开号：

  US05252578A1
• 作为产物：
  描述：

  N-(4-溴丁基)邻苯二甲酰亚胺 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 5-methoxy-3,4-dihydro-3--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

文献信息

• 3-aminochroman compounds
  申请人：Adir et Compagnie

  公开号：US05252578A1

  公开（公告）日：1993-10-12

  The invention relates to the derivatives of general 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, 1.ltoreq.n.ltoreq.6, R.sub.3 represents a nitrile group, an optionally substituted amino group or any one of the groups described in the description, and medicinal products.

  本发明涉及一般式(I)的衍生物：##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，1≤n≤6，R.sub.3代表腈基、可选取代的氨基或描述中的任意一种基团，以及药物制剂。
• US5314907A
  申请人：——

  公开号：US5314907A

  公开（公告）日：1994-05-24
• US5273994A
  申请人：——

  公开号：US5273994A

  公开（公告）日：1993-12-28
• 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.