5-methoxy-3--3,4-dihydro-2H-1-benzopyran | 138277-81-3

• 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--3,4-dihydro-2H-1-benzopyran
• 英文别名: 5-METHOXY-(+)-3-[N-n-PROPYL-N-(CYANOMETHYL)AMINO]CHROMAN；2-[(5-methoxy-3,4-dihydro-2H-chromen-3-yl)-propylamino]acetonitrile
• CAS: 138277-81-3；155787-46-5；155787-47-6
• 化学式: C₁₅H₂₀N₂O₂
• 分子量: 260.336
• InChiKey: CIURNMFRBRAFLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-3--3,4-dihydro-2H-1-benzopyran 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-METHOXY-3-{N-PROPYL-N-[2-(4-TOLUENESULFONYLAMINO)ETHYL]AMINO}CHROMAN
  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：

  5-methoxy-3-propionamido-3,4-dihydro-2H-1-benzopyran 在 dimethyl sulfide borane 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 5-methoxy-3--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

文献信息

• 3-aminochroman compounds
  申请人：Adir et Compagnie

  公开号：US05510374A1

  公开（公告）日：1996-04-23

  The invention relates to compounds of the formula (I): ##STR1## in which: Z represents oxygen, R.sub.1 represents alkyl, R.sub.2 represents hydrogen or alkyl, n represents 1 through 6, R.sub.3 represents unsubstituted or substituted phenylacylamino, and antidepressive and other medicinal products containing the same.

  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。
• 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
• 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