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- W2892451531 abstract "3,5-Bis(arylidene)-4-piperidone (BAP) derivatives display good antitumour and anti-inflammatory activities because of their double α,β-unsaturated ketone structural characteristics. If N -benzenesulfonyl substituents are introduced into BAPs, the configuration of the BAPs would change significantly and their anti-inflammatory activities should improve. Four N -benzenesulfonyl BAPs, namely (3 E ,5 E )-1-(4-methylbenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C 28 H 21 F 6 NO 3 S·CH 2 Cl 2 , ( 4 ), (3 E ,5 E )-1-(4-fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one, C 27 H 18 F 7 NO 3 S, ( 5 ), (3 E ,5 E )-1-(4-nitrobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one, C 27 H 18 F 6 N 2 O 5 S, ( 6 ), and (3 E ,5 E )-1-(4-cyanobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C 28 H 18 F 6 N 2 O 3 S·CH 2 Cl 2 , ( 7 ), were prepared by Claisen–Schmidt condensation and N -sulfonylation. They were characterized by NMR, FT–IR and HRMS (high resolution mass spectrometry). Single-crystal structure analysis reveals that the two 4-(trifluoromethyl)phenyl rings on both sides of the piperidone ring in ( 4 )–( 7 ) adopt an E stereochemistry of the olefinic double bonds. Molecules of both ( 4 ) and ( 6 ) are connected by hydrogen bonds into one-dimensional chains. In ( 5 ) and ( 7 ), pairs of adjacent molecules embrace through intermolecular hydrogen bonds to form a bimolecular combination, which are further extended into a two-dimensional sheet. The anti-inflammatory activity data reveal that ( 4 )–( 7 ) significantly inhibit LPS-induced interleukin (IL-6) and tumour necrosis factor (TNF-α) secretion. Most importantly, ( 6 ) and ( 7 ), with strong electron-withdrawing substituents, display more potential inhibitory effects than ( 4 ) and ( 5 )." @default.
- W2892451531 created "2018-10-05" @default.
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- W2892451531 date "2018-09-28" @default.
- W2892451531 modified "2023-10-12" @default.
- W2892451531 title "Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives" @default.
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- W2892451531 doi "https://doi.org/10.1107/s2053229618013232" @default.
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