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

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.

New Synthesis of N‐(1H‐pyrazol‐5‐yl)‐hexahydroquinoline‐3‐carbonitrile and octahydropyrazolo[4′,3′:5,6]pyrimido[1,2‐a]quinoline‐6‐carbonitrile Derivatives from the Cyclic β‐Enaminones

“…Copolymers of quinoline derivatives undergo hierarchical self‐assembly into nanostructure and mesostructure having electronic and photonic functions . Given the biological importance of quinoline‐3‐carbonitrile and as part of our ongoing research in this area, we synthesized a novel series of tetrahydroquinoline‐3‐carbonitriles, bearing pyrazole moiety at N1 and octahydropyrazolo[4′,3′:5,6]pyrimido[1,2‐ a ]quinoline‐6‐carbonitrile derivatives.…”

Dapson in Heterocyclic Chemistry, Part V: Synthesis, Molecular Docking and Anticancer Activity of Some Novel Sulfonylbiscompounds Carrying Biologically Active Dihydropyridine, Dihydroisoquinoline, 1,3-Dithiolan, 1,3-Dithian, Acrylamide, Pyrazole, Pyrazolopyrimidine and Benzochromenemoieties

“…Negative regulation of this pathway could arrest the cascade of these events and will inhibit the proliferation of cancer cells. 19,20) On the preceding and as a part of our studies on new heterocyclic compounds derived from Dapson as new potential anticancer agents, [21][22][23][24] we have synthesized a novel series of dihydropyridines, dihydroisoquinolines, 1,3-dithiolan, 1,3-dithian, acrylamide, pyrazole, pyrazolopyrimidine and benzochromene derivatives to evaluate their anticancer activity. (SO 2 ).…”