Dapson in Heterocyclic Chemistry,Part IV: Synthesis of Some Novel Diphenylsulfones Containing Acetamide,Pyrrolidine, Piperazine,and Thiomorpholine Moieties as Antimicrobial and Antitumor Agents |
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Authors: | M M Ghorab M S A El Gaby N E Amin N M H Taha M A Shehab I M I Faker |
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Institution: | 1. Department of Drug Radiation Research , National Center for Radiation Research and Technology (NCRRT) , Nasr City, Cairo, Egypt;2. Organic Chemistry Department, Faculty of Science for Boys , Al-Azhar Universty , Asute, Cairo, Egypt;3. Organic Chemistry Department, Faculty of Science for Girls , Al-Azhar Universty , Cairo, Egypt;4. Applied Organic Chemistry Department , National Research Center , Cairo, Egypt |
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Abstract: | 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. |
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Keywords: | Diphenylsulfone having acetamide pyrrolidine piperazine thiomorpholine as antitumor and antimicrobial activities |
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