Dapson in Heterocyclic Chemistry, Part IV: Synthesis of Some Novel Diphenylsulfones Containing Acetamide, Pyrrolidine, Piperazine, and Thiomorpholine Moieties as Antimicrobial and Antitumor Agents

Interaction of dapson [bis(4-aminophenyl)sulfone] 1 with [bis-(methylsulfonyl) methylidine]malononitrile 2 yielded the corresponding dicyano derivative 3, which was reacted with acetic anhydride, succinic anhydride, 4-chlorobenzaldehyde, phenyl isothiocyanate to give the corresponding acetamide 4, succinamic acid 5, pyrrolidine 6, Shiff base 7 and thiourea 8, respectively. Treatment of 3 with chloroacetyl chloride afforded the aminoacetyl chloride derivative 9. Further, the interaction of compound 9 with thioglycolic acid, malononitrile, ethyl glycinate hydrochloride, and/or potassium thiocyanate furnished compounds 10–15, respectively. The structural characterization of the prepared compounds was based on microanalytical and spectroscopic analyses. Some of the prepared compounds were tested for their antimicrobial and antitumor activities. Compounds 9 and 12 showed promising antitumor activity compared with Doxorubicin as positive control.