Nitroimidazole derivatives have been prepared and investigated for therapeutic and prophylactic applications. Numerous compounds have been used as antibacterial, antiprotozoic, antimycotic, immunosuppressive and radiosensitizing agents. It has been usually established that 5-nitro derivatives are more active than 4-nitro isomers.
Our earlier investigations have been devoted to synthesis and antifungal as well as antibacterial properties of N-phenacyl-4,5-dinitroimidazole derivatives [1,2]. In this communication we report on the synthesis of new compounds with adamantacyl group at the N-1 position of heterocyclic ring. The syntheses of new compounds (9-11), are based on analogous reaction. The starting materials 4,5-dinitro-, 2-methyl-4,5-dinitro- and 2,4-dinitroimidazoles have been prepared according to the methods described in the literature [3-5]. Dinitroimidazoles 5, 6 and 8 were alkylated with adamantyl bromomethyl ketone in absolute ethanol in the presence of sodium etoxide. The treatment of N-substituted dinitroimidazole (9-11) with cyclic amines (e.g. morpholine), led to the derivative of 4-amino-5-nitroimidazole (e.g. 12). Similar products were also formed in the reaction of respective N-phenacyl derivatives [6]. All newly obtained compounds are expected to show antiviral activity.

where: R = H, CH₃; a = 65% HNO₃/H₂SO₄, boiling; b = 100% HNO₃/H₂SO₄, boiling; c = CH₃COOH/HNO₃/(CH₃CO)₂O, r.t., 48 h; d = chlorobenzene, 115-120 °C, 10 h; e = adamantyl bromomethyl ketone, Na/EtOH, boiling; f = morpholine, THF, r.t.

[1] Zaprutko L. et al., Pharmazie 44 (1989) 81; [2] Zaprutko L. et al., Pharmazie 47 (1992) 258; [3] Fargher R.G. et al., J. Chem. Soc. 115 (1919) 217; [4] Novikov S.S. et al., Khimia Geter. Soed. Nr 6 (1970) 503; [5] Bulusu S. et al., J. Phys. Chem. 99 (1995) 5009; [6] Zaprutko L. et al., Monatsch. Chem. 134 (2003) 1145.

Acknowledgements: This work was supported by KBN Grant No. 2 PO5F 039 27.

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