Exploring the molecular characteristics of a benzoindoleninyl-pyrazolo[3,4- b ]pyridine

Abstract A new benzoindolenine containing a fused pyrazolo[3,4- b ]pyridine moiety was synthesized in 51 % yield and structurally characterized using spectroscopic techniques. The reaction mechanism suggests that the fused bicyclic ring is generated via the formation of C=N and C–C bonds. X-ray crystallographic analysis reveals that the molecule is planar with both moieties adopting an anti -conformation, and its intermolecular noncovalent C–H⋯π, π⋯π, C–H⋯N, and H⋯H interactions were accessed by Hirshfeld surface analysis. The compound displayed a bathochromic fluorescence shift from solution to the solid state, and the nature of the photoluminescence decay was investigated. Furthermore, the compound was subjected to in silico ADMET analyses, which indicated compliance with all Veber’s rules and several criteria of Lipinski’s rule of five. The compound was also tested for antibacterial and antifungal activities, but showed no appreciable potency towards the tested microbial strains.