isatin | 946689-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: isatin
• 英文别名: 1,5-Diethylindole-2,3-dione
• CAS: 946689-27-6
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: ZOXHUQCBPXBTJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4’-亚甲基-双-(3-氯-2,6-二乙基苯胺) 、 isatin 以 乙醇 为溶剂， 生成 (3E)-3-[3-chloro-4-[[2-chloro-4-[(E)-(1,5-diethyl-2-oxo-indolin-3-ylidene)amino]-3,5-diethyl-phenyl]methyl]-2,6-diethyl-phenyl]imino-1,5-diethyl-indolin-2-one
  参考文献：
  名称：

  Computational evaluation and experimental in vitro antibacterial, antifungal and antiviral activity of bis-Schiff bases of isatin and its derivatives

  摘要：

  A computational model has been developed for the rational design of bioactive pharmacophore sites as an antibacterial, antifungal and antiviral candidates based on available X-ray structures of bis-Schiff bases (Blagus et al., Maced J Chem Chem Eng 29:117-138, 2010; Nabei et al., Polyhedron 28:1734-1739, 2009; Zhang et al., Inorg Chem Commun 14:1636-1639, 2011; Zhong et al., Eur J Med Chem 41:1090-1092, 2006; Zhou et al., Inorg Chim Acta 359:1442-1448, 2006). A dozen of bis-Schiff bases 3-14 of isatin, benzylisatin and 5-fluoroisatin 1a-c were designed using this model. The compounds were screened for antibacterial, antifugal and antiviral activity against a panel of DNA and RNA viruses. The most potent of these compounds 8 and 11 was tested in viral cultures for their ability to present a potential (O delta--N delta-) antiviral pharmacophore site. Compounds 8 and 11 were the most cytotoxic in HEL cells. All these synthesized bis-Schiff bases were also tested for their antibacterial and antifungal activities. They did not display activity against S. cerevisiae (ATCC 28383) or C. albicans (CIP 1180-79); may be because they did not have an antibacterial pharmacophore site (X delta--Y delta+). The best inhibitors tested in vitro against HIV-1 are genetically predisposed to be inhibited by similar pharmacophore sites. The results from all the aspects of this bioinformatic approaches are discussed as par with our experience with screening candidates.

  DOI：

  10.1007/s00044-012-0127-6