5-(3-chlorophenyl)-2,3-dihydroinden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-(3-chlorophenyl)-2,3-dihydroinden-1-one
• 英文别名: 5-(3-Chlorophenyl)indan-1-one
• 化学式: C₁₅H₁₁ClO
• 分子量: 242.705
• InChiKey: GWQJIGXYHXRGEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(3-chlorophenyl)-2,3-dihydroinden-1-one 、 硫脲 在 碘 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以67%的产率得到6-(3-chlorophenyl)-4H-indeno[1,2-d][1,3]thiazol-1-ium-2-amine;iodide
  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：

  5-溴茚酮 、 3-氯苯硼酸 在 palladium diacetate 、 四丁基溴化铵 、 potassium carbonate 作用下， 以74%的产率得到5-(3-chlorophenyl)-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

• Use of polycyclic thiazole systems for the treatment of obesity
  申请人：AventisPharma Deutschland GmbH

  公开号：US06329407B1

  公开（公告）日：2001-12-11

  The invention relates to the use of polycyclic thiazole systems and their physiologically tolerated salts and physiologically functional derivatives for the treatment of obesity. The treatment involves administration of a compound of formula I, in which the radicals have the stated meanings, and of their physiologically tolerated salts and physiologically functional derivatives.

  本发明涉及使用多环噻唑系统及其生理上可耐受的盐和生理上功能衍生物治疗肥胖症。该治疗涉及给予公式I的化合物，其中基团具有所述的含义，以及它们的生理上可耐受的盐和生理上功能衍生物。
• Polycyclic thiazole systems, processes for their preparation and pharmaceuticals comprising these compounds
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06187801B1

  公开（公告）日：2001-02-13

  The invention relates to polycyclic thiazole systems and their physiologically tolerated salts and physiologically functional derivatives. Compounds of the formula I, in which the radicals have the stated meanings, and their physiologically tolerated salts and processes for their preparation are described. The compounds are suitable, for example, as anorectics.

  本发明涉及多环噻唑系统及其生理耐受盐和生理功能衍生物。本发明描述了式I的化合物及其生理耐受盐，并描述了其制备过程。这些化合物例如可用作压抑食欲的药物。
• VERWENDUNG VON POLYCYCLISCHEN THIAZOL-SYSTEMEN ZUR HERSTELLUNG VON MEDIKAMENTEN ZUR PROPHYLAXE ODER BEHANDLUNG VON OBESITAS
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1156805A2

  公开（公告）日：2001-11-28
• VERWENDUNG VON POLYZYKLISCHEN THIAZOL-SYSTEMEN ZUR HERSTELLUNG VON MEDIKAMENTEN ZUR PROPHYLAXE ODER BEHANDLUNG VON OBESITAS
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1156805B1

  公开（公告）日：2004-08-11
• POLYCYCLISCHE THIAZOL-SYSTEME UND IHRE VERWENDUNG ALS ANOREKTIKA
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1183247A1

  公开（公告）日：2002-03-06