Abstract
AbstractA new series of quinoxaline 1,4‐dioxides, structurally related to the benzotriazine tirapazamine 1 have been prepared starting from 5,6‐dichlorobenzofuroxane 2. The Beirut reaction between 2 and alkyl or aryl thiopropanones afforded the 2‐methyl‐3‐alkyl(aryl)thioquinoxaline 1,4‐dioxides 3a‐3e. Selective oxidation of 3 with m‐chloroperbenzoic acid yielded the sulphinyl 4a‐4c and sulphonyl 5a‐5b derivatives. Replacement of the sulphonyl group of 5a by chlorine or bromine gave 6 or 7, while nucleophilic displacement by 3‐(N,N‐dimethylamino)propylamine afforded 8. A dimer 9 was prepared from 5a and hydrazine hydrate. The methylthio group of 3a was replaced by using formamidine acetate giving the amino compound 10. Bromination of the methyl group of 3b afforded 11, which reacted with 2‐aminoethanol giving 12. Compounds were tested as cytotoxic agents both in oxic and in hypoxic cells.
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