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Thermal Properties and Degradation of N-Carbamoyl Benzotriazole Derivatives

Hydroxyurea and hydroxyurea derivatives showed versatile biological activity and are employed in treatment of various neoplastic and non-neoplastic diseases such as various types of cancer, sickle cell anemia, HIV infection, thrombocythemia and psoriasis. N-substituted benzotriazoles are well known as useful synthons in synthesis of carbamates, ureas, semicarbazides and carbazides. In this paper we have explored thermal decomposition of 1-(N-benzyloxycarbamoyl) benzotriazole, and its structural analogues 1-(N-metoxycarbamoyl) benzotriazole, 1-(N-ethoxycarbamoyl) benzotriazole, as well as thermal properties of N, N', N''-tribenzyloxyisocyanuric acid. These compounds show cytotoxic potential against monocytic THP-1 cell lines, whereas N, N', N''-tribenzyloxyisocyanuric acid showed antimicrobial activity on E. coli strains. Thermal properties of N- carbamoyl benzotriazole derivatives and N, N', N''- tribenzyloxyisocyanuric acid were investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The results revealed a difference between structural analogs of N-carbamoyl benzotriazole derivatives, and seem to be in agreement with the previously proposed formation of N, N', N''-tibenzyloxyisocynauric acid during the heating process of 1-(N-benzyloxycarbamoyl) benzotriazole, via an intermediary N-benzyloxyisocyanate. Substantially different thermal properties were observed for other structural analogues, 1-(N-metoxycarbamoyl) benzotriazole and 1-(N- ethoxycarbamoyl) benzotriazole. In contrast to N- benzyloxyisocyanate, their decomposition products, i.e. metoxyisocyanate and ethoxyisocyanate, do not undergo a similar cyclization reaction.

1-(N-benzyloxycarbamoyl) benzotriazole; 1-(N-metoxycarbamoyl) benzotriazole; 1-(N-ethoxycarbamoyl) benzotriazole; N; N'; N''-tribenzyloxyisocyanuric acid; Thermogravimetric analysis (TGA); Differential scanning calorimetry (DSC)

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