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Understanding Chemistry and Unique NMR Characters of Novel Amide and Ester Leflunomide Analogues

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Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt
2
Department of Molecular Genetics, Denver, University of Colorado, Aurora, CO 80045, USA
3
Department of Chemistry, Georgia State University, Atlanta, GA 30303-3083, USA
*
Author to whom correspondence should be addressed.
Magnetochemistry 2017, 3(4), 41; https://doi.org/10.3390/magnetochemistry3040041
Received: 17 November 2017 / Revised: 28 November 2017 / Accepted: 29 November 2017 / Published: 5 December 2017
A series of diverse substituted 5-methyl-isoxazole-4-carboxylic acid amides, imide and esters in which the benzene ring is mono or disubstituted was prepared. Spectroscopic and conformational examination was investigated and a new insight involving steric interference and interesting downfield deviation due to additional diamagnetic anisotropic effect of the amidic carbonyl group and the methine protons in 2,6-diisopropyl-aryl derivative (2) as conformationaly restricted analogues Leflunomide was discussed. Individual substituent electronic effects through π resonance of p-substituents and most stable conformation of compound (2) are discussed. View Full-Text
Keywords: leflunomide derivatives; 2,6-diisopropylphenyl anilide chemical shift abnormalities; 5-methyl-4-isoxazole derivatives leflunomide derivatives; 2,6-diisopropylphenyl anilide chemical shift abnormalities; 5-methyl-4-isoxazole derivatives
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Henen, M.A.; Hamdi, A.; Farahat, A.A.; Massoud, M.A.M. Understanding Chemistry and Unique NMR Characters of Novel Amide and Ester Leflunomide Analogues. Magnetochemistry 2017, 3, 41.

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