European Journal of Chemistry 2011, 2(1), 18-24 | doi: https://doi.org/10.5155/eurjchem.2.1.18-24.125 | Get rights and content






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Synthesis, configuration and properties of some new 3,4,5-substituted oxazolidin-2-ones


Anelia Tsenova Mavrova (1,*) , Pavletta Stoyanova Denkova (2) , Jordan Andreev Tsenov (3)

(1) University of Chemical Technology and Metallurgy, Sofia, BG-1756, Bulgaria
(2) Institute of Organic Chemistry, Bulgarian Academy of Science, Sofia, BG-1113, Bulgaria
(3) Institute of Organic Chemistry, Bulgarian Academy of Science, Sofia, BG-1113, Bulgaria
(*) Corresponding Author

Received: 25 May 2010 | Revised: 28 Dec 2010 | Accepted: 08 Dec 2010 | Published: 28 Mar 2011 | Issue Date: March 2011

Abstract


Novel 3,4,5-substituted-oxazolidin-2-ones containing piperazine, 1-(4-chlorophenyl) piperazine, benzhydrylpiperazine, morpholine and piperidine rings were synthesized via Mannich reaction. The stereochemistry of syn and anti-isomers was assigned using the observed differences in the chemical shifts of the oxazolidinone ring protons and the values of vicinal coupling constants (3J) between the two protons of the oxazolidin-2-one ring. For all compounds NOE (Nuclear Overhauser Effect) NMR spectra were measured in order to prove additionally the position of the substituents in the oxazolidin-2-one ring. Some physic chemical, steric and electronic properties of the compounds were determined in order to establish the similarity between the synthesized and reference compounds. The performed computations showed that the anti-isomers possessed lower electronic energies in comparison to these of syn-compounds. The nucleus-nucleus repulse energies (NRE) and the highest occupied molecular orbital energies (HOMO) of the anti-isomers are higher than the HOMO and NRE energies of syn-compounds. The Connolly Solvent Accessible Surface Area (SAS) and Connolly Molecular Surface Area (MS) values of anti-isomers are lower than these of syn-isomers. The same relations were observed for the reference compounds. Probably the differences in the electronic and steric properties are responsible not only for the higher LD50 value of the reference anti-compound, but also may contribute to the higher toxicity of the prepared anti-Mannich bases in comparison to that of the syn-diastereoisomers.

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Keywords


Oxazolidin-2-ones; Stereochemistry; Configuration; Mannich reaction; Analgesis activity; Drug similarity

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DOI: 10.5155/eurjchem.2.1.18-24.125

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Funding information


Thanks are due to National Science Fund/Ministry of Education and Science grant X1408 and Science Fund/Chemical Technology and Metallurgy University grant 10580 for the financial support of this work.

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How to cite


Mavrova, A.; Denkova, P.; Tsenov, J. Eur. J. Chem. 2011, 2(1), 18-24. doi:10.5155/eurjchem.2.1.18-24.125
Mavrova, A.; Denkova, P.; Tsenov, J. Synthesis, configuration and properties of some new 3,4,5-substituted oxazolidin-2-ones. Eur. J. Chem. 2011, 2(1), 18-24. doi:10.5155/eurjchem.2.1.18-24.125
Mavrova, A., Denkova, P., & Tsenov, J. (2011). Synthesis, configuration and properties of some new 3,4,5-substituted oxazolidin-2-ones. European Journal of Chemistry, 2(1), 18-24. doi:10.5155/eurjchem.2.1.18-24.125
Mavrova, Anelia, Pavletta Stoyanova Denkova, & Jordan Andreev Tsenov. "Synthesis, configuration and properties of some new 3,4,5-substituted oxazolidin-2-ones." European Journal of Chemistry [Online], 2.1 (2011): 18-24. Web. 1 Oct. 2020
Mavrova, Anelia, Denkova, Pavletta, AND Tsenov, Jordan. "Synthesis, configuration and properties of some new 3,4,5-substituted oxazolidin-2-ones" European Journal of Chemistry [Online], Volume 2 Number 1 (28 March 2011)

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DOI Link: https://doi.org/10.5155/eurjchem.2.1.18-24.125

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