5-(benzofuran-2-yl)-2,3-dihydroinden-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 5-(benzofuran-2-yl)-2,3-dihydroinden-1-one
• 英文别名: 5-(1-Benzofuran-2-yl)-2,3-dihydroinden-1-one
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: VCCPWFVCERBRGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(benzofuran-2-yl)-2,3-dihydroinden-1-one 、 硫脲 在 碘 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以63%的产率得到6-(benzofuran-2-yl)-8H-indeno[1,2-d]thiazol-2-ylamine hydroiodide
  参考文献：
  名称：

  6-Aryl-8H-indeno[1,2-d]thiazol-2-ylamines:  A₁ Adenosine Receptor Agonist Allosteric Enhancers Having Improved Potency

  摘要：

  Allosteric enhancers (AEs) of the A(1) adenosine receptor (A(1)AR) have potential as drugs for treating neurological, cardiovascular, and renal diseases. This report describes the synthesis and evaluation of a series of 6-aryl-8H-indeno[1,2-d]thiazol-2-ylamines that exhibited AE activity at the A(1)AR. Palladium-mediated condensation of arylboronic acids with 5-bromoindan-1-one generated arylindanones 2a-aj for iodine-catalyzed condensation with thiourea, generating 2-aminothiazolium salts 3a-aj. Binding studies using membranes from cells stably expressing human A(1)ARs, A(2A)ARs, or A(3)ARs evaluated AE activity and receptor subtype selectivity. The EC50 of the AE activities of compounds 3m-o, 3x, and 3ae were 2.2, 1.5, 0.9, 1.0, and 3.0,mu M, respectively, substantially lower than that of the well characterized 2-amino3-aroylthiophene (PD 81,723), > 10 mu M. The new compounds also have substantially higher maximal AE activity. These compounds had no AE activity at the A(2A)AR and only minimal activity at the A(3)AR.

  DOI：

  10.1021/jm049132j
• 作为产物：
  描述：

  苯并呋喃-2-硼酸 、 5-溴茚酮 在 palladium diacetate 、 四丁基溴化铵 、 potassium carbonate 作用下， 以72%的产率得到5-(benzofuran-2-yl)-2,3-dihydroinden-1-one
  参考文献：
  名称：

  6-Aryl-8H-indeno[1,2-d]thiazol-2-ylamines:  A₁ Adenosine Receptor Agonist Allosteric Enhancers Having Improved Potency

  摘要：

  Allosteric enhancers (AEs) of the A(1) adenosine receptor (A(1)AR) have potential as drugs for treating neurological, cardiovascular, and renal diseases. This report describes the synthesis and evaluation of a series of 6-aryl-8H-indeno[1,2-d]thiazol-2-ylamines that exhibited AE activity at the A(1)AR. Palladium-mediated condensation of arylboronic acids with 5-bromoindan-1-one generated arylindanones 2a-aj for iodine-catalyzed condensation with thiourea, generating 2-aminothiazolium salts 3a-aj. Binding studies using membranes from cells stably expressing human A(1)ARs, A(2A)ARs, or A(3)ARs evaluated AE activity and receptor subtype selectivity. The EC50 of the AE activities of compounds 3m-o, 3x, and 3ae were 2.2, 1.5, 0.9, 1.0, and 3.0,mu M, respectively, substantially lower than that of the well characterized 2-amino3-aroylthiophene (PD 81,723), > 10 mu M. The new compounds also have substantially higher maximal AE activity. These compounds had no AE activity at the A(2A)AR and only minimal activity at the A(3)AR.

  DOI：

  10.1021/jm049132j

文献信息

• 6-Aryl-8<i>H</i>-indeno[1,2-<i>d</i>]thiazol-2-ylamines:  A₁ Adenosine Receptor Agonist Allosteric Enhancers Having Improved Potency
  作者：Mahendra D. Chordia、Molly Zigler、Lauren J. Murphree、Heidi Figler、Timothy L. Macdonald、Ray A. Olsson、Joel Linden

  DOI：10.1021/jm049132j

  日期：2005.8.1

  Allosteric enhancers (AEs) of the A(1) adenosine receptor (A(1)AR) have potential as drugs for treating neurological, cardiovascular, and renal diseases. This report describes the synthesis and evaluation of a series of 6-aryl-8H-indeno[1,2-d]thiazol-2-ylamines that exhibited AE activity at the A(1)AR. Palladium-mediated condensation of arylboronic acids with 5-bromoindan-1-one generated arylindanones 2a-aj for iodine-catalyzed condensation with thiourea, generating 2-aminothiazolium salts 3a-aj. Binding studies using membranes from cells stably expressing human A(1)ARs, A(2A)ARs, or A(3)ARs evaluated AE activity and receptor subtype selectivity. The EC50 of the AE activities of compounds 3m-o, 3x, and 3ae were 2.2, 1.5, 0.9, 1.0, and 3.0,mu M, respectively, substantially lower than that of the well characterized 2-amino3-aroylthiophene (PD 81,723), > 10 mu M. The new compounds also have substantially higher maximal AE activity. These compounds had no AE activity at the A(2A)AR and only minimal activity at the A(3)AR.