Naproxen in heterocyclic chemistry: Novel syntheses of triazoles, triazolothiadiazines, triazolothiadiazoles, and triazolothiadiazepine bearing an asymmetric carbon atom and radiostability of the biologically active compounds

Several s-triazoles 2, 7a, 10, 12; s-triazolo[3,4-b][1,3,4]thiadiazines (3-5); s-triazolo[3,4b][1,3,4]thiadiazoles (6, 8, 11, 15); and s-triazolo[3,4b][1,3,4]thiadiazepine (14) were synthesized starting from 2-(6-methoxy-2-naphthyl)propanoic acid (1) (Naproxen). The structures of the synthesized compounds were elucidated by elemental analyses and spectral data. Compounds 2, 5, 11, 12, 14, and 15 exhibited a remarkable antifungal activity compared with the standard fungicide Mycostatine. Radiosterilization of the biologically active compounds 2, 5, 11, and 14 in the dry state may prove to be applicable (retaining their structures unchanged up to 40 kGy). (C) 2002 Wiley Periodicals, Inc.