Sharon A. Jennings

Antitumour imidazotetrazines. Part 39. Synthesis of bis(imidazotetrazine)s with saturated spacer groups

Bis(imidazotetrazine)s (16), related in structure to the antitumour agents mitozolomide (1a) and temozolomide (1b), but linked through the N(3)–N(3′) atoms of the imidazo[5,1-d][1,2,3,5]tetrazine ring-systems, are prepared by interaction of 5-diazoimidazole-4-carboxamide (8) and diisocyanates (15). The presence of the polymethylene linker with/without sulfur and oxygen heteroatoms does not substantially affect the acid stability, base-catalysed decomposition, antitumour activity or DNA base alkylation preference characteristic of the unlinked imidazotetrazines mitozolomide and temozolomide.

Biarylpyrimidines: a new class of ligand for high-order DNA recognitionElectronic supplementary information (ESI) available: experimental details of UV melting studies and example spectroscopic and analytical data. See http://www.rsc.org/suppdata/cc/b3/b301554h/

Biarylpyrimidines bearing omega-aminoalkyl substituents have been designed as ligands for high-order DNA structures: spectrophotometric, thermal and competition equilibrium dialysis assays showed that changing the functional group for substituent attachment from thioether to amide switches the structural binding preference from triplex to tetraplex DNA; the novel ligands are non-toxic and moderate inhibitors of human telomerase.