Abstract
The reaction of 2-naphthaloxyacetic acid with thiosemicarbazide in the presence of phosphoryl chloride, followed by treatment with phenacylbromides, led to the formation of imidazo[2,1-b][1,3,4]thiadiazoles 3a—c. 2-(Naphthalen-3-yloxy)acetohydrazide 4 on treatment with ethyl 2-(2-arylhydrazono)-3-oxobutanoates (5a—c), 2-methoxymethylene)malononitrile, or ethyl 2-cyano-3,3-bis(methylthio)acrylate led to the formation of substituted pyrazoles 6—8. The reaction of the hydrazide 4 with hydrazonoyl chlorides 9a—c and 1,2,4,5-benzene tetracarboxylic-1,2:4,5-dianhydride produced bis-diazo compounds 10a—c and dimide 11 respectively. All new compounds were tested for their protective activity against DNA damage induced by bleomycin–iron complex. Compound 2 showed the greatest protection against DNA damage, thus diminishing chromogen formation between the damaged DNA and thiobarbituric acid.
