Synthesis of Spirooxindoles and Study of their Self‐Assembly features; Hirshfeld Surface, Energy Framework andIn Silicoanalysis

Abstract

AbstractIn this study, the 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitrile derivatives were synthesized, crystallized, and their molecular geometries were established by the SCXRD method. The significance of weak intermolecular interactions in the self‐assembly of 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitriles was then investigated. The supramolecular framework analysis indicated that 2‐oxospiro[indoline‐3,4′‐pyran]‐5′‐carbonitriles establish their network in self‐assembly mainly by N−H⋅⋅⋅O, N−H⋅⋅⋅N, C−H⋅⋅⋅O, C−H⋅⋅⋅C, C−H⋅⋅⋅N, and C−H⋅⋅⋅π interactions. The energy framework analysis revealed the dominant contribution of electrostatic energy in the crystal packing of the titled compounds. The PASS prediction of the titled compounds has shown a reasonably good affinity towards Insulin‐regulated aminopeptidase. Further, the molecular docking study with Insulin‐regulated aminopeptidase receptor has shown the higher affinity of the titled compounds to the zinc binding pocket over the other pockets.