Letter: Electron Impact Mass Spectrometry Study of a Series of Substituted 5-Aminoalkylmethyl-Cytosines and Their 1- N -( o-,m- and p -)Bromobenzyl-Substituted Derivatives
Restricted accessResearch articleFirst published online December, 2007
Letter: Electron Impact Mass Spectrometry Study of a Series of Substituted 5-Aminoalkylmethyl-Cytosines and Their 1- N -( o-,m- and p -)Bromobenzyl-Substituted Derivatives
The electron-impact mass spectra of 5-aminoalkylmethyl-substituted cytosine and of their 1-N-o-(m- or p-) bromobenzyl-substituted derivatives are discussed. The influence of 5-aminoalkyl and 1-N-bromobenzyl substituents on the mode of mass fragmentation occurring upon electron impact ionization was demonstrated. The fragmentation pathways of all compounds and the characteristic ions in these spectra originating from the McLafferty rearrangement, RDA reactions and simple cleavages are presented.
BakerB.R.KelleyJ.L., “Irreversible enzyme inhibitors. CXXX. Cytosine nucleosidedeaminase 2. Hydrophobic bonding with disubstituted uracils and cytosines”, J. Med. Chem.11, 686 (1968). doi: 10.1021/jm00310a011
3.
BakerB.R.WardA.D., “Irreversible enzyme inhibitors. 200. Active-site directed inhibitors of deoxycytidine kinase”, J. Med. Chem.20, 88 (1977). doi: 10.1021/jm00211a018
4.
SchroederA.C.HugesR.G.JrBlochA., “Synthesis and biological effects of acyclic pyrimidine nucleoside analogs”, J. Med. Chem.24, 1078 (1981). doi: 10.1021/jm00141a012
5.
MotawiaM.S.Abdel-MegiedA.E.-S.PedersenE.B.NielsenC.M.EbbsenP., “Synthesis of 5-alkoxymethyl derivatives of 3′-amino-2′,3′-dideoxyuridine and evaluation of their activity against HIV and cancer”, Acta Chem. Scand.46, 77 (1992).
6.
KamalakannanP.VenkappayyaD.BalasubramanianT., “A new antimetabolite, 5-morpholinomethyl-2-thiouracil-spectral properties, thermal profiles, antibacterial, antifungal and antitumor studies of some of its metal chelates”, J. Chem. Soc., Dalton Trans.3381 (2002).
7.
PrukałaD., “New compounds via Mannich reaction of cytosine, paraformaldehyde and cyclic secondary amines”, Tetrahedron Lett.47, 9045 (2006). doi: 10.1016/j.tetlet.2006.10.117
8.
PrukałaD., “Synthesis and physicochemical properties of new 1-N o-(m- or -p)bromobenzyl-substituted derivatives of 5-(aminodialkyl)methylcytosine”, J. Het. Chem.44, 1207 (2007).
9.
WyrzykiewiczE.PospiesznyT.SobolewskaM., “Electron ionization induced mass spectra study of new isomeric 2-o-(m- and p-)nitrobenzylthio-5-piperidinomethyl (morpholinomethyl) uracils and 1,2-di-o-(m- and p-) nitrobenzol-5-piperidinomethyl (morpholinomethyl)-2-thiouracils”, Rapid Commun. Mass Spectrum.20, 713 (2006). doi: 10.1002/rcm.2338
10.
DuffieldA.M.BudzikiewiczH.WilliamsD.H.DjerassiC., “Mass spectrometry in structural and stereo-chemical problems. LXIV.1 A study of the fragmentation processes of some cyclic amines”, J. Am. Chem. Soc.87, 810 (1965). doi: 10.1021/ja01082a021
11.
RiceJ.M.DudekG.O.BarberM., “Mass spectra of nucleic acid derivatives. Pyrimidines”, J. Am. Chem. Soc.87, 4569 (1965). doi: 10.1021/ja00948a029
12.
McLaffertyF.W.TurečekF., Interpretation of mass spectra (4th Edn). University Science Books, California, USA (1993).
13.
WyrzykiewiczE.PospiesznyT.BarłógA., “Electron impact mass spectral study of 1,2-di-o-(m- and p-)nitro(bromo-)benzyl-2-thio-6-methyluracils”, Rapid Commun. Mass Spectrom.19, 580 (2005). doi: 10.1002/rcm.1801
14.
WyrzykiewiczE.PospiesznyT.MielcarekS., “Syntheses, EIMS, 1H NMR, and 13C NMR study of 2-mono, 1,2-di, and 2,4-di-substituted derivatives of 2-thiocytosine”, Phosphorus, Sulfur and Silicon and the Related Elements180, 2051 (2005). doi: 10.1080/104265090902840
15.
WyrzykiewiczE.SzponarA., “Syntheses, EIMS and 13C NMR study of 1,2-disubstituted derivatives of 2-thio-6-aminouracil”, Phosphorus, Sulfur and Silicon and the Related Elements178, 2263 (2003). doi: 10.1080/713744574
