Selected Sulfonyl Compounds as Anticancer/Antimalarial Agents

Abstract

The synthesis and biological testing of a series of sulfonyl phenols and sulfonyl aryl methyl ethers has revealed that p-methoxyphenyl p-toluenesulfonate is a very selective and effective antimalarial agent which shows pronounced activity against human skin cancer cells. Application of a counter-attack strategy permits the direct preparation of the requisite tosylate ether from the bis(tosylate) of dihydroquinone.

The crystal structure of 2,6-di-tert-butyl-4-(phenyl(phenylsulfonyl)methyl)phenol, C27H32O3S

“…The diarylmethyl sulfones as one of the most important sulfur-containing compounds are widely present in many biologically active natural products and pharmaceuticals [4][5][6][7]. For example, 2-(1-((4-chlorophenyl)sulfonyl)cyclohexyl)-1,4-difluorobenzene as a γ-secretase inhibitor show high potential in the treatment of Alzheimer's disease [4].…”

“…4,4′,4′′-((Phenylsulfonyl)methanetriyl)tris(fluorobenzene) is useful [1,4]diazepine as an antidepressant drug has a wider therapeutic spectrum and can exert sufficient therapeutic effects in a short period [6]. 9-((4-Methoxyphenyl)sulfonyl)-9H-fluorene is a very selective and effective antimalarial agent, which shows pronounced activity against human skin cancer cells [7]. In addition, diarylmethylamines are also widely used as important synthetic intermediates in medicinal chemistry and materials science [8][9][10].…”

TBAB-Catalyzed 1,6-Conjugate Sulfonylation of para-Quinone Methides: A Highly Efficient Approach to Unsymmetrical gem-Diarylmethyl Sulfones in Water

“…As a class of sulfur-containing compounds, sulfones are widely used in organic synthesis, pharmaceuticals, agrochemicals, and materials science [1][2][3][4][5][6][7]. Among the sulfone family, diarylmethyl sulfones hold an essential position in biologically important compounds that show various biological activities, such as potassium channel inhibitory activity [8], as well as antidepressant [9] and anticancer properties (Figure 1) [10]. Additionally, diarylmethyl sulfones can be applied as useful intermediates for synthetic applications owing to the versatile reactivities of the sulfonyl group activated carbanions [1,[11][12][13][14].…”

Diversity-Oriented Synthesis of Functionalized Diaryl Sulfones by Regio­selective [3+3] Cyclizations of 1,3-Bis(siloxy)buta-1,3-dienes with 2-(Aryl­sulfonyl)-3-ethoxy-2-en-1-ones: Scope and Limitations

“…The wide range of pharmacological activities reported include, for example, antibacterial activity, 1 inhibition of phospholipidase A 2 , 2 inhibition of catechol O-methyltransferase, 3 inhibition of dihydropteroate synthase of Escherichia coli, 4 hypolipidemic activity, 5 cytotoxicity against HeLa cells and the antipicornavirus, 6 neuropeptide Y 1 receptor binding activity, 7 anti-HIV activity, 8 anticholesteremic activity, 9 binding to human muscarinic M 1 and M 2 receptors, 8c,10 histamine H 3 -receptor antagonistic activity, 11 antiprotozoal activity, 12 binding to neuroblastoma cells, 13 binding to the human cannabinoid CB 1 receptor, 14 and inhibition of the main protease of the recombinant SARS coronavirus. 15 A number of synthetic approaches to diaryl sulfones have been reported.…”