Abstract
Drug discoveries require the iterative synthesis—along with structural studies—of numerous individual analogues of biologically and medicinally active compounds. Over half of all known compounds and a large number of pharmaceutical products are heterocyclic in nature. The pharmacological activity of drugs depends mainly on interaction with their biological targets, which have a complex three-dimensional structure, and molecular recognition is guided by the nature of the intermolecular interactions. Furthermore, the drug's polymorphic nature also adversely affects its abilities. In order to address these factors, the stereochemical analysis of various piperidine and azepine derivatives, weak π-interaction analysis of isoxazole, imidazole, indole, quinoline and triazole and polymorphic analysis of two commercial drugs, valdecoxib and sildenafil citrate were carried out. Only the crystal structures were used for these analyses, of which the piperidine and azepine derivatives, valdecoxib and sildenafil citrate were solved by our group. To understand the structure-activity relationship, the results of these studies were correlated with the crystal structure of their respective drug molecules that are found in complex with the receptors. Stereochemical analysis showed that the ring conformation and orientation of the substituents correlate well with the active conformation of the drug. The π-systems prefer to form an offset stacking π…π interaction geometry similar to the phenylalanine–phenylalanine interactions in proteins. In the polymorphic analysis one of the crystal conformations of valdecoxib proved to have better interaction with its receptor indicating higher activity.
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Acknowledgments
SMMS and KS thank the Council of Scientific and Industrial Research (CSIR), Government of India for the award of the Senior Research Fellowship and acknowledge the useful discussion with their colleague Mr. N. Sampath. MNP, SMMS, and KS thank the University Grants Commission (UGC) and the Department of Science & Technology (DST), Government of India for financial support to the Department of Crystallography and Biophysics under the UGC-SAP and DST-FIST programmes.
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Ponnuswamy, M.N., Gromiha, M.M., Sony, S.M.M., Saraboji, K. Conformational Aspects and Interaction Studies of Heterocyclic Drugs. In: Gupta, S.P. (eds) QSAR and Molecular Modeling Studies in Heterocyclic Drugs I. Topics in Heterocyclic Chemistry, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_027
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