Electron ionization mass spectral fragmentation of new (E)-4-chalconylothioalkyl-substituted derivatives of piperidinie, 4-methyl-piperidine, morpholine and piperazine as well as (E)-4-bromoalkylthiochalcones, being substrates of the former compounds, have been studied. Fragmentation pathways have been proposed on the basis of the accurate mass and metastable transition measurements.
De VincenzoR.FerliniC.DistefanoM.GagginiC.RivaA.BombardelliE.MorazzoniP.ValentiP.BellutiF.RanelletiF.O.MancusoS.ScambiaG., “In vitro evaluation of newly developed chalcone analogues in human cancer cells”, Cancer Chemother. Pharmacol.46, 305 (2000). doi: 10.1007/s002800000160
2.
GoM.L.WuX.LiuX.L., “Chalcones: An update on cytotoxic and chemoprotective properties”, Curr. Med. Chem.12, 483 (2005).
3.
LiuM.WilairatP.CroftS.L.TanA. Lay-ChooGoM.L., “Structure–activity relationships of antileishmanial and antimalarial chalcones”, Bioorg. Med. Chem.11, 2729 (2003). doi: 10.1016/S0968-0896(03)00233-5
4.
AntoR.SukumaranK.KuttanG.RaoM.SubbarajuV.KuttarR., “Anticancer and antioxidant activity of synthetic chalcones and related compounds”, 97, Cancer Lett.33 (1995). doi: 10.1016/0304-3835(95)03945-S
5.
LopezS.CastelliM.V.ZacchinoS.DominguezJ.N.LoboG.Charris-CharrisJ.CoetrsJ.C.C.RibasJ.C.DeviaC.RodriguesA.M.EnrizR.D., “In vitro antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal call wall”, Bioorg. Med. Chem.9, 1999 (2001). doi: 10.1016/S0968-0896(01)00116-X
6.
BinderD.NoeC.R.HolzerW.RosenwirthB., “Thiophene as a structural element of physiologically active substances.12. Thiophene analogs of antiviral chalcones”, Archiv der Pharmazie318, 49 (1985).
7.
LevaiA.PatonayT., “Synthesis of leukotriene analogue carboxylic acid derivatives of dihydrochalcones”, Pharmazie50, 429 (1995).
8.
MentleinR.VowinkelE., “Ortho effect in the fragmentation of 2-acethoxychalcones under electron impact”, Org. Mass Spectrom.19, 330 (1984). doi: 10.1002/oms.1210190708
9.
ArdanazC.E.KavkaJ.CurcurutoO.TraldiP.GuidugliF., “On the structure of [C9H6O]+ ions originating by electron impact induced decomposition of chalcone”, Rapid Commun. Mass Spectrom.5, 569 (1991). doi: 10.1002/rcm.1290051115
10.
ArdanazC.E.KavkaJ.GuidugliF.FavrettoD.TraldiP., “An unexpected methyl loss observed in electron ionization of chalcones”, Rapid Commun. Mass Spectrom.12, 139 (1998). doi: 10.1002/(SICI)1097-0231(19980214)12:3<139::AID-RCM128>3.0.CO;2-G
11.
NowakowskaZ., “Electron ionization induced fragmentation of 4-hydroxychalcone derivatives”, Rapid Commun. Mass Spectrom.16, 634 (2002). doi: 10.1002/rcm.596
12.
NowakowskaZ., “Structural assignment of chalcones and differentiation of their isomeric derivatives by electron ionization induced fragmentation”, Rapid Commun. Mass Spectrom.18, 2513 (2004). doi: 10.1002/rcm.1643
13.
ZhangJ.BrodbeltJ.S., “Structural characterization and isomer differentiation of chalcones by electrospray ionization tandem mass spectrometry”, J. Mass Spectrom.38, 555 (2003). doi: 10.1002/jms.472
14.
McLaffertyF.W.TurečekF., Interpretation of mass spectra, Fourth Edition. University Science Books, Mill Valley, California, USA (1993).