4-(2,3-dihydro-benzofuran-5-yl)-butyric acid amide | 211692-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 4-(2,3-dihydro-benzofuran-5-yl)-butyric acid amide
• 英文别名: 4-(2,3-Dihydro-benzofuran-5-yl)-buttersaeure-amid；4-(2,3-Dihydro-1-benzofuran-5-yl)butanamide
• CAS: 211692-47-6
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: QYFSZEROWLVGIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2,3-dihydro-benzofuran-5-yl)-butyric acid amide 在 盐酸 、 dimethyl sulfide borane 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 9.0h， 生成 8-{2-[4-(2,3-Dihydro-benzofuran-5-yl)-butylamino]-ethoxy}-6-fluoro-chroman-4-one
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists

  摘要：

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.

  DOI：

  10.1021/jm9707840
• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 palladium on activated charcoal ammonium hydroxide 、 三氯化铝 、 草酰氯 、 氢气 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 4-(2,3-dihydro-benzofuran-5-yl)-butyric acid amide
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists

  摘要：

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.

  DOI：

  10.1021/jm9707840

文献信息

• Chatelus, Annales de Chimie (Cachan, France), 1949, vol. <12> 4, p. 505,526
  作者：Chatelus

  DOI：——

  日期：——
• Cagniant; Cagniant, Bulletin de la Societe Chimique de France, 1955, p. 931,933
  作者：Cagniant、Cagniant

  DOI：——

  日期：——
• N-HETEROCYCLIC DERIVATIVES AS NOS INHIBITORS
  申请人：BERLEX LABORATORIES, INC.

  公开号：EP1206467A1

  公开（公告）日：2002-05-22
• ＮＯＳ阻害剤としてのＮ−複素環式誘導体
  申请人：バーレックス ラボラトリーズ,インコーポレイティド

  公开号：JP4739625B2

  公开（公告）日：2011-08-03
• [EN] N-HETEROCYCLIC DERIVATIVES AS NOS INHIBITORS<br/>[FR] DERIVES N-HETEROCYCLIQUES SOUS FORME D'INHIBITEURS OXYDE NITRIQUE SYNTHASE
  申请人：BERLEX LAB

  公开号：WO2001014371A1

  公开（公告）日：2001-03-01

  N-Heterocyclic derivatives of formula (Ya) are described herein, as well as other N-heterocycles, as inhibitors of nitric oxide synthase. Pharmaceutical compositions containing these compounds, methods of using these compounds as inhibitors of nitric oxide synthase and processes for synthesizing these compounds are also described herein.