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Synthesis, antiviral, and cytotoxic investigation of imidazo[4,5-a]acridones

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Abstract

The importance of virus infections and the early successes with some antiviral drugs have prompted the search for new agents, and it has been focused on compounds that are active against herpesviruses, retroviruses, and rhinoviruses. In this paper, 3H-imidazo[4,5-a]acridones are introduced as new antiviral agents against a panel of DNA and RNA viruses, including herpes simplex virus-1 (KOS), herpes simplex virus-2 (G), vaccinia virus, vesicular stomatitis virus, and herpes simplex virus-1 TK-KOS ACV r. Also, these compounds were cytostatic in the higher micromolar range. 3H-imidazo[4,5-a]acridones were synthesized by Tanasescu reaction of 3H-imidazo[4′,5′:3,4]benzo [c]isoxazoles in concentrated sulfuric acid containing nitrous acid in excellent yields. The advanced compounds were obtained from the reaction of N-alkyl-5-nitrobenzimidazoles with different aryl acetonitriles under basic conditions. Structures of all newly synthesized compounds were confirmed by IR, 1H NMR, and mass spectral data. The results indicated that the title compounds have mild-to-potent activities in comparison with their appropriate reference standards.

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Correspondence to Mehdi Pordel.

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Daghigh, L.R., Pordel, M., Davoodnia, A. et al. Synthesis, antiviral, and cytotoxic investigation of imidazo[4,5-a]acridones. Med Chem Res 24, 3912–3919 (2015). https://doi.org/10.1007/s00044-015-1438-1

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  • DOI: https://doi.org/10.1007/s00044-015-1438-1

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