(3Z)-5-methoxy-1H-indole-2,3-dione 3-[(3-tert-butylphenyl)hydrazone] | 1263428-99-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3Z)-5-methoxy-1H-indole-2,3-dione 3-[(3-tert-butylphenyl)hydrazone]
• 英文别名: 3-[2-(3-tert-butylphenyl)hydrazinyl]-5-methoxyindol-2-one
• CAS: 1263428-99-4
• 化学式: C₁₉H₂₁N₃O₂
• 分子量: 323.395
• InChiKey: CMBIRDSRQAYJLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  62.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  5-甲氧基靛红 、 1-[3-叔丁基苯基]肼盐酸盐 以 甲醇 为溶剂， 以100%的产率得到(3Z)-5-methoxy-1H-indole-2,3-dione 3-[(3-tert-butylphenyl)hydrazone]
  参考文献：
  名称：

  Synthesis and biophysical evaluation of arylhydrazono-1H-2-indolinones as β-amyloid aggregation inhibitors

  摘要：

  A series of isatin-3-arylhydrazones were synthesized and evaluated in vitro as inhibitors of A beta(1-40) aggregation using a thioflavin T fluorescence method. An exploration of the effects on A beta(1-40) aggregation of a number of diverse substituents at phenylhydrazone group and 5,6- positions of the indolinone nucleus led us to single out some new anti-aggregating compounds with IC50 values in the low micromolar range. The most active compounds carry methoxy- or hydroxy- substituents in the indolinone 5,6-positions and lipophilic groups such as iPr and Cl at 4'- and 3'-position, respectively, of the phenylhydrazone moiety. Two derivatives are noteworthy, namely 18 (IC50 = 0.4 mu M) and 42 (IC50 = 1.1 mu M). The in vitro effects of the highly active, water soluble, compound 42 on the temporal evolution of A beta(1-40) fibrils formation were further investigated by circular dichroism spectroscopy, transmission electron microscopy and dynamic light scattering studies, which clearly showed that this compound delayed and lowered the amyloid fibril formation. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.015

文献信息

• Synthesis and biophysical evaluation of arylhydrazono-1H-2-indolinones as β-amyloid aggregation inhibitors
  作者：Francesco Campagna、Marco Catto、Rosa Purgatorio、Cosimo D. Altomare、Angelo Carotti、Angelo De Stradis、Gerardo Palazzo

  DOI：10.1016/j.ejmech.2010.11.015

  日期：2011.1

  A series of isatin-3-arylhydrazones were synthesized and evaluated in vitro as inhibitors of A beta(1-40) aggregation using a thioflavin T fluorescence method. An exploration of the effects on A beta(1-40) aggregation of a number of diverse substituents at phenylhydrazone group and 5,6- positions of the indolinone nucleus led us to single out some new anti-aggregating compounds with IC50 values in the low micromolar range. The most active compounds carry methoxy- or hydroxy- substituents in the indolinone 5,6-positions and lipophilic groups such as iPr and Cl at 4'- and 3'-position, respectively, of the phenylhydrazone moiety. Two derivatives are noteworthy, namely 18 (IC50 = 0.4 mu M) and 42 (IC50 = 1.1 mu M). The in vitro effects of the highly active, water soluble, compound 42 on the temporal evolution of A beta(1-40) fibrils formation were further investigated by circular dichroism spectroscopy, transmission electron microscopy and dynamic light scattering studies, which clearly showed that this compound delayed and lowered the amyloid fibril formation. (C) 2010 Elsevier Masson SAS. All rights reserved.