2-((2-(2-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione | 1224734-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-((2-(2-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione
• 英文别名: 2-[[2-(2-chlorophenyl)hydrazinyl]methylidene]indene-1,3-dione
• CAS: 1224734-29-5
• 化学式: C₁₆H₁₁ClN₂O₂
• 分子量: 298.729
• InChiKey: ATVQXQXZDWLBKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-dimethylaminomethyleneindane-1,3-dione 、 (2-氯苯基)-肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以60%的产率得到2-((2-(2-chlorophenyl)hydrazinyl)methylene)-1H-indene-1,3(2H)-dione
  参考文献：
  名称：

  Design, synthesis and biological evaluation of indane-2-arylhydrazinylmethylene-1,3-diones and indol-2-aryldiazenylmethylene-3-ones as β-amyloid aggregation inhibitors

  摘要：

  Biological screening of (hetero)aromatic compounds allowed the identification of some novel inhibitors of A beta(1-40) aggregation, bearing indane and indole rings as common scaffolds. Molecular decoration of lead compounds led to inhibitors exhibiting a potency, measured by the Thioflavin T fluorimetric assay, ranging from high to low micromolar IC50. The 2-(p-isopropylphenyldiazenylmethylene)indolone derivative 6c resulted as the most potent aggregation inhibitor exhibiting an IC50 of 1.4 mu M, with complete lack of fibril formation as confirmed by transmission electron microscopy. Structure activity relationships suggested that binding to the AB peptide may be largely guided by pi-stacking and hydrogen bond interactions. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.029

文献信息

• Design, synthesis and biological evaluation of indane-2-arylhydrazinylmethylene-1,3-diones and indol-2-aryldiazenylmethylene-3-ones as β-amyloid aggregation inhibitors
  作者：Marco Catto、Rosaria Aliano、Angelo Carotti、Saverio Cellamare、Fausta Palluotto、Rosa Purgatorio、Angelo De Stradis、Francesco Campagna

  DOI：10.1016/j.ejmech.2009.12.029

  日期：2010.4

  Biological screening of (hetero)aromatic compounds allowed the identification of some novel inhibitors of A beta(1-40) aggregation, bearing indane and indole rings as common scaffolds. Molecular decoration of lead compounds led to inhibitors exhibiting a potency, measured by the Thioflavin T fluorimetric assay, ranging from high to low micromolar IC50. The 2-(p-isopropylphenyldiazenylmethylene)indolone derivative 6c resulted as the most potent aggregation inhibitor exhibiting an IC50 of 1.4 mu M, with complete lack of fibril formation as confirmed by transmission electron microscopy. Structure activity relationships suggested that binding to the AB peptide may be largely guided by pi-stacking and hydrogen bond interactions. (C) 2009 Elsevier Masson SAS. All rights reserved.