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A series of 3-(benzyl-substituted)-imidazo[5,1- d ]-1,2,3,5-tetrazines ( 13 ) and related derivatives with 3-heteromethyl groups has been synthesised and screened for growth-inhibitory activity in vitro against two pairs of glioma cell lines with temozolomide-sensitive and -resistant phenotypes dependent on the absence/presence of the DNA repair protein O  6 -methylguanine-DNA methyltransferase (MGMT). In general the compounds had low inhibitory activity with GI 50 values &gt;50 μM against both sets of cell lines. Two silicon-containing derivatives, the TMS-methylimidazotetrazine ( 9 ) and the SEM-analogue ( 10 ), showed interesting differences: compound ( 9 ) had a profile very similar to that of temozolomide with the MGMT+ cell lines being 5 to 10-fold more resistant than MGMT- isogenic partners; the SEM-substituted compound ( 10 ) showed potency across all cell lines irrespective of their MGMT status.

medchemcomm

Synthesis and growth-inhibitory activities of imidazo[5,1-<i>d</i>]-1,2,3,5-tetrazine-8-carboxamides related to the anti-tumour drug temozolomide, with appended silicon, benzyl and heteromethyl groups at the 3-position

Synthesis and growth-inhibitory activities of imidazo[5,1-d]-1,2,3,5-tetrazine-8-carboxamides related to the anti-tumour drug temozolomide, with appended silicon, benzyl and heteromethyl groups at the 3-position