Quantum Mechanical Modeling of N4-(2, 5-Disubstituted phenyl) Semicarbazones: Synthesis and Anticonvulsant Activity of N4-(2, 5-dimethylphenyl/ -2-fluoro-5-methyl phenyl) Semicarbazones

M.      Shalini; P.      Yogeeswari; D.      Sriram; P.      Kudyar; P. Roheeth      Kumar; S.      Induja; J.   P.   Stables

doi:10.2174/1573406410602060617

Abstract

Two new series of N4-(2, 5-disubstitutedphenyl) semicarbazones were synthesized and evaluated for the anticonvulsant activity in various animal models of seizures. Quantum mechanical modeling was carried out on these compounds to understand the structural features essential for activity. The higher the difference in HOMO and LUMO energy levels the greater was the activity profile. Substitution with fluoro group on the ortho position of the aryl ring was found to decrease the reactivity and hence the activity profile of aryl semicarbazones, which has been justified with the molecular orbital surface analysis of the synthesized compounds.

Keywords: Aryl semicarbazones, Anticonvulsant, HOMO and LUMO energy, HOMO surfaces

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Medicinal Chemistry

Title: Quantum Mechanical Modeling of N4-(2, 5-Disubstituted phenyl) Semicarbazones: Synthesis and Anticonvulsant Activity of N4-(2, 5-dimethylphenyl/ -2-fluoro-5-methyl phenyl) Semicarbazones

Volume: 2 Issue: 6

Author(s): M. Shalini, P. Yogeeswari, D. Sriram, P. Kudyar, P. Roheeth Kumar, S. Induja and J. P. Stables

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Keywords: Aryl semicarbazones, Anticonvulsant, HOMO and LUMO energy, HOMO surfaces

Abstract: Two new series of N4-(2, 5-disubstitutedphenyl) semicarbazones were synthesized and evaluated for the anticonvulsant activity in various animal models of seizures. Quantum mechanical modeling was carried out on these compounds to understand the structural features essential for activity. The higher the difference in HOMO and LUMO energy levels the greater was the activity profile. Substitution with fluoro group on the ortho position of the aryl ring was found to decrease the reactivity and hence the activity profile of aryl semicarbazones, which has been justified with the molecular orbital surface analysis of the synthesized compounds.

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Shalini M., Yogeeswari P., Sriram D., Kudyar P., Kumar P. Roheeth, Induja S. and Stables P. J., Quantum Mechanical Modeling of N4-(2, 5-Disubstituted phenyl) Semicarbazones: Synthesis and Anticonvulsant Activity of N4-(2, 5-dimethylphenyl/ -2-fluoro-5-methyl phenyl) Semicarbazones, Medicinal Chemistry 2006; 2 (6) . https://dx.doi.org/10.2174/1573406410602060617