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A series of thiophene incorporating pyrazolone moieties 5a–f and 6a–c were synthesized via diazo coupling of diazonium salt of 3-substituted-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophenes 1a–c with 3-methyl-1H-pyrazol-5(4H)-one, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one or 3-amino-1H-pyrazol-5(4H)-one, respectively. Newly synthesized dyes were applied to polyester fabric as disperse dyes in which their color measurements and fastness properties were evaluated. These dyes showed generally red to blue shifted color with high extinction coefficient in comparison with aniline-based azo dyes. The antitumor activity of the synthesized dyes was evaluated. The results showed clearly that most of them exhibited good activity and compounds 5c and 5d exhibited moderate activity.

A few new sulphadimidine incorporating thiophene moiety are synthesized. These compounds were assessed by analytical and spectral data. Antioxidant evaluation for the investigated compounds was evaluated by ABTS assay and bleomycin-dependent DNA-damage; the compounds exhibited weak activities.

A series of aryl azonaphthoquinones 8a-e were obtained via coupling of the corresponding diazonium salts 7a-c with naphthoquinones 2 or 3 in pyridine. Moreover, treatment of 5 with 6a, b in ethanol containing potassium carbonate afforded the corresponding enaminones 9a, b, respectively. Furthermore, heating of 6a with 2-hydroxy-3-((piperidn- 1-yl)methyl)naphthalene-1,4-dione 10 in EtOH/AcOHor sodium 3,4-dihydro-3,4-dioxonaphthalene-1-sulphonate 1 in MeOH/H2O afforded the corresponding enaminones 11 and 12, respectively. The newly synthesized compounds were screened for their antioxidant activity. Compounds 8b 89.87, 9a (89.93%) and 9b (95.97%) exhibited promising activities. On the other hand compounds 8b, 9a, 9b, 11 and 12 have the ability to protect DNA from the damage induced by bleomycin.