New imidazolidineiminothione derivatives: Synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities

Ziad Moussa, Marwa A.M.Sh El-Sharief, Samir Y. Abbas

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

A series of new imidazolidineiminothione derivatives with various halogenated and alkylated aromatic substituents at N-(1) and at N-(3) was synthesized through the reaction of N-arylcyanothioformamides with arylisocyanate derivatives. Structure of imidazolidineiminothione derivatives were established based on spectroscopic IR,1H NMR,13C NMR,1H,1H-COSY, HSQC,19F NMR, MS and elemental analyses data. Evaluation of antitumor, antiviral, antibacterial and antifungal activities for the synthesized compounds were carried out to probe their activities. Most of the synthesized compounds displayed antitumor activity. The presence of 3,5-dichlorophenyl moiety at N-(1) and trichlorophenyl moiety on N-(3) (2f) resulted the highest cytotoxic activity. The presence of 9H-fluorenyl moiety on N-(3) resulted in the lowest cytotoxic activity. The antiviral screening displayed that 2d and 2f were markedly active against one or two viral strains. Compound 2d (3,5-dichlorophenyl moiety at N-(1) and 4-chlorophenyl moiety on N-(3)) showed 100% antiviral effect toward HAV. Compound 2f showed 96.7% antiviral effect toward HSV1 and 80.3% antiviral effect toward HAV. The antimicrobial activity suggested that all of the imidazolidineiminothione derivatives possess significant antimicrobial activity against most of the test organisms. Some imidazolidineiminothione derivatives showed MIC values of antibacterial and antifungal activities ranged from 0.78 to 6.25 μg/ml.

Original languageEnglish
Pages (from-to)419-428
Number of pages10
JournalEuropean Journal of Medicinal Chemistry
Volume122
DOIs
Publication statusPublished - 2016
Externally publishedYes

Keywords

  • Antibacterial
  • Antifungal activities
  • Antitumor
  • Antiviral
  • Imidazolidineiminothiones
  • N-Arylcyanothioformamides
  • NMR spectra

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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