Conformational Polymorphism in Sulfonylurea Drugs: Electronic Structure Analysis
| Autor: | Sandeep Sundriyal, Prasad V. Bharatam, Nikunjkumar Patel, Yoganjaneyulu Kasetti |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
medicine.drug_class
Hydrogen bond Chemistry Stereochemistry Molecular Conformation Hydrogen Bonding Crystal structure Electronic structure Tautomer Sulfonylurea Surfaces Coatings and Films Solvent Sulfonylurea Compounds Computational chemistry Intramolecular force Materials Chemistry medicine Quantum Theory Thermodynamics Gases Physical and Theoretical Chemistry Conformational isomerism |
| Zdroj: | The Journal of Physical Chemistry B. 114:11603-11611 |
| ISSN: | 1520-5207 1520-6106 |
| DOI: | 10.1021/jp101327k |
| Popis: | Quantum chemical calculations have been performed using HF, B3LYP, and MP2 methods on the model sulfonylurea PhSO(2)NHC(=O)NHMe to understand the conformational and tautomeric preferences. The results indicate that a conformer with intramolecular hydrogen bond SLU-1 (hitherto not considered) is more stable than the conformer SLU-2 (which is generally considered) for sulfonylureas. The energy difference between these two conformers is about 4 kcal/mol in the gas phase; however, the energy differences between the two rotamers become negligible in the solvent phase. Iminol tautomeric forms of sulfonylurea (which were also not studied until now) are only about 5-6 kcal/mol higher in energy as per both gas-phase and solvent-phase analyses, indicating easy accessibility of tautomeric states in sulfonylureas. Quantum chemical analysis has also been carried out on the possible dimeric structures of these three important isomers of sulfonylurea, and correlations have been made to the known crystal structures of polymorphic states of sulfonylurea drugs. |
| Databáze: | OpenAIRE |
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