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 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].…”
Section: Commentmentioning
confidence: 99%
“…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].…”
“…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].…”
Section: Commentmentioning
confidence: 99%
“…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].…”
“…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].…”
A highly efficient sulfonylation of para-quinone methides with sulfonyl hydrazines in water has been developed on the basis of the mode involving a tetrabutyl ammonium bromide (TBAB)-promoted sulfa-1,6-conjugated addition pathway. This reaction provides a green and sustainable method to synthesize various unsymmetrical diarylmethyl sulfones, showing good functional group tolerance, scalability, and regioselectivity. Further transformation of the resulting diarylmethyl sulfones provides an efficient route to some functionalized molecules.
“…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.…”
The formal [3+3] cyclization of 1,3-bis(siloxy)buta-1,3-dienes with 2-(arylsulfonyl)-3-ethoxy-2-en-1-ones, readily available by reaction of b-keto sulfones with triethyl orthoformate, allows the synthesis of a variety of functionalized diaryl sulfones with very good regioselectivity.
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