Abstract
Two new isomeric oxazolidin-2-one derivatives have been synthesized through reaction of (E)-3-styrylquinoxalin-2-one with bis-dichloroethylamine hydrochloride in presence of potassium carbonate. The structures of the formed products were established by NMR and mass spectroscopy. The fragmentation patterns of the two novel synthesized oxazolidin-2-ones (1, 2), possessing the same backbone structure, were investigated using electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS) techniques. A simple methodology, based on the use of ESI (positive ion mode) and by increasing the declustering potential in the atmospheric pressure/vacuum interface, collision induced dissociation (CID), was used to enhance the formation of the fragment ions. In general, the novel synthetic oxazolidin-2-one derivatives afforded, in the gas phase, protonated molecules leading to the confirmation of the molecular masses and chemical structures of the studied compounds. The breakdown routes of the protonated molecules were rationalized by conducting low-energy collision CID-MS/MS analyses (product ion scans) using. The structural similarity between the two studied oxazolidin-2-ones explains the similarity observed in their CID-MS/MS spectra and their fragmentation pathways. ESI-MS/MS recorded with increased collision energy values permits us to observe different product ions and allow us to differentiate the two studied isomers. ESI-MS and CID-MS/MS analyses have thus proven to be a specific and very sensitive method for the structural investigation of the two novel synthesized oxazolidin-2-one derivatives.
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References
Ford CW, Zurenko GE, Barbachyn MR (2001) The discovery of linezolid, the first oxazolidinone antibacterial agent. Curr Drug Targ Infect Dis 1:181–199
Kim SH, Jung MH, Yoo KH, Cho JH, Oh CH (2008) Synthesis and antibacterial activities of novel oxazolidinones having cyclic sulfonamide moieties. Bioorg Med Chem Let 18:5815–5818
Gregory WA WA, Brittelli DR DR, Wang CLJ CLJ, Wuonola MA MA, Mc Ripley RJ RJ, Eustice DC DC, Eberly VS VS, Bartholomew PT PT, Slee AM, PT FM (1989) Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxo-oxazolidines. J Med Chem 32:1673–1681
Hideaki K, Masayuki M, Hiroyki K, Tetsu-ichiro KMK, Hiroyuki O (1999) Cytoxazone: a novel cytokine modulator containing a 2-oxazolidinone ring produced by Streptomyces sp. J Org Chem 64:1052–1053
Wouters VJ (1998) Use of chiral glycerol 2,3-carbonate in the synthesis of 3-aryl-2-oxazolidinone. Curr Med Chem 5:137–162
Gottschlich C, Ruecker H (1992) (5S)-3-aryl-5-(1-piperidinylmethyl)-2-oxazolidinones, a new class of potential neuroleptics with a high affinity for sigma receptors. Bioorg Med Chem Lett 2:165–116
Jeon H, Jo N, Cho J, Oh CH (2007) Synthesis and antibacterial evaluation of 1β-methyl-2-[5-(1-methoxyimino-2-substituted sulfonamide ethyl)pyrrolidin-3-ylthio] carbapenems and their related compounds. Eur J Med Chem 42:358–366
Evans DA, Ny HP, Rieger DL (1993) Total synthesis of the macrolide antibiotic Rutamycin B. J Am Chem Soc 115:11446–11459
Jones TK, Reamer RA, Desmond R, Mills SG (1990) Chemistry of tricarbonyl hemiketals and application of Evans technology to the total synthesis of the immunosuppressant (−)-FK-506. J Am Chem Soc 112:2998–3017
Bouzina A, Grib I, Bechlem K, Belhani B, Aouf N-E, Berredjem M (2016) Efficient synthesis of novel N-acylsulfonamide oxazolidin-2-ones derivatives. Karbala Int J Mod Sci 2:98–103
Sebbar NK, Mekhzoum MEM, Essassi EM, Zerzouf A, Talbaoui A, Bakri Y, Saadi M, LEI A (2016) Novel 1,4-benzothiazine derivatives: synthesis, crystal structure, and anti-bacterial properties. Res Che Intermed 42:6845–6862
Ramli Y, Essassi EM (2015) Advances in synthetic approaches, functionnalization and biological properties of Quinoxaline derivatives. In: Taylor J C (ed) Advances in chemistry research, Volume 27, Nova Science Publishers, Inc, New York, pp 109–160. ISBN:978-1-63482-545-00
Alsubar A, Bouhfid R, Essassi EM (2009) Synthesis of new oxindole derivatives containing an oxazolidin-2-one. ARKIVOC 12:337–346
Caleb AA, Bouhfid R, Essassi EM, El Ammari L (2009) 3-[2-(3-methyl-2-oxo-1,2-dihydroquinoxalin-1-yl)ethyl]oxazolidin-2-one. Acta Cryst E65:o2024–o2025
Bouayad K, Kandri Rodi Y, Ouzidan Y, Essassi EM, Saadi M, El Ammari L (2015) Crystal structure of 5-chloro-1,3-bis[2-(2- oxo-1,3-oxazolidin-3-yl)ethyl]-1H-benzimidazol 2(3H)-one. Acta Cryst E71:o735–o736
Daouda B, Doumbia ML, Essassi EM, Saadi M, El Ammari L (2013) 3-[2-(3-phenyl-2-oxo-1,2-dihydroquinoxalin-1-yl)ethyl]-1,3-oxazolidin-2-one. Acta Cryst E69:o662
Ramli Y, Zouihri H, Essassi E, Ng SW (2012) 3-{2-[(3-{(E)-2-[4-(Dimethylamino)- phenyl]ethenyl}quinoxalin-2-yl)oxy]- ethyl}-1,3-oxazolidin-2-one monohydrate. Acta Cryst E68:o241
Ouzidan Y, Kandri Rodi Y, Fronczek FR, Venkatraman R, El Ammari L, Essassi EM (2011) 1,3-Bis[2-(2-oxo-1,3-oxazolidin-3-yl)- ethyl]-1H-benzimidazol-2(3H)-one. Acta Cryst E67:o362–o363
Ouzidan Y, Jasinski JP, Butcher RJ, Golen JA, Essassi EM, El Ammari L (2011) 3-[2-(6-Bromo-2-phenyl-3H-imidazo- [4,5-b]pyridin-3-yl)ethyl]-1,3-oxazolidin- 2-one. Acta Cryst E67:o1095
Daouda B, Brelot L, Doumbia ML, Essassi EM, Ng SW (2011) 3-{2-[(3-Phenylquinoxalin-2-yl)oxy]- ethyl}-1,3-oxazolidin-2-one>. Acta Cryst E67:o1235
Ahmed Moussaif A, Essassi EM, Lazar S, Zouihri H, Leger JM (2010) 3-[2-(1H-Benzimidazol-2-ylsulfanyl)- ethyl]-1,3-oxazolidin-2-one. Acta Cryst E66:o3137
Daouda B, Ahabchane NH, Zouihri H, Essassi EM, Ng SW (2010) 1-[2-(2-Oxo-1,3-oxazolidin-3-yl)ethyl]-4- phenyl-1H-1,5-benzodiazepin-2(3H)-one. Acta Cryst E66:o2080
Bel-Ghacham H, Kandri Rodi Y, Saffon N, Essassi EM, Ng SW (2010) 6-Bromo-1-[2-(2-oxo-1,3-oxazolidin-3- yl)ethyl]-1H-imidazo[4,5-b]pyridin- 2(3H)-one. Acta Cryst E66:o456
Abdussalam Alsubari A, Bouhfi R, Zouihri H, Essassi EM, Seik Weng Ng SW (2010) 3-[2-(5H-Indolo[2,3-b]quinoxalin-5-yl)- ethyl]-1,3-oxazolidin-2-one. Acta Cryst E66:o2461
Ahoya CA, Rachid Bouhfid R, Ballo Daouda B, Essassi EM, El Ammari L (2010) 3-[2-(3-Methylquinoxalin-2-yloxy)ethyl]-1,3-oxazolidin-2-one. Acta Cryst E66:o1050
Banoub J. (ed) (2011) Detection of biological agents for the prevention of terrorism. NATO science for peace and securuty Series A.: Chemistry and biology, DOI 10. 1007/978-90-481-9815-3_1, Springer Science+Business Media B. V 319–360.
Joly N, El Aneed A, Martin P, Banoub J (2005) Structural determination of the novel fragmentation routes of morphine opiate receptor antagonists using electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Rapid Commun Mass spectrom 19:3119–3130
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*This work is dedicated to the memory of Dr. Ahoya Anothane Caleb.
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Caleb, A.A. et al. (2017). Synthesis and ESI-MS/MS Fragmentation Study of Two New Isomeric Oxazolidin-2-One Derivatives. In: Banoub, J., Caprioli, R. (eds) Molecular Technologies for Detection of Chemical and Biological Agents. NATO Science for Peace and Security Series A: Chemistry and Biology. Springer, Dordrecht. https://doi.org/10.1007/978-94-024-1113-3_15
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DOI: https://doi.org/10.1007/978-94-024-1113-3_15
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