Synthesis, crystal structure, anti-cancer, anti-inflammatory anti-oxidant and quantum chemical studies of 4-(pyrrolidine-2,5‑dione‑1-yl)phenol

•Synthesis, biological studies, comparison of theoretical and experimental spectroscopic results.•DFT and quantum chemical calculations i.e. B3LYP/cc-pVTZ and PBE0/cc-pVTZ level.•MEP map shows phenyl ring has negative and pyrrolidine ring slight positive electrostatic potential.•Important peaks in mass spectrum were also reproduced by simulated mass spectrum.•The compound has exhibited better anti-infammatory activity than ibuprofen besides exhibiting significant anticancer activity for HT-29 cell line. 4-(Pyrrolidine-2,5‑dione‑1-yl)phenol (PDP) prepared by establishing a new protocol from 4-aminophenol and succinic anhydride using glacial acetic acid as a solvent. The structure of PDP was initially verified by FT-IR, 1H and 13C NMR spectroscopy and further confirmed by single crystal XRD and mass spectrometry techniques. These properties of PDP were also evaluated by DFT, TD-DFT and quantum chemical methods. The molecular structure of PDP was computationally examined by density functional theory (DFT/B3LYP/cc-pVTZ and DFT/PBE0/cc-pVTZ methods). The MEP map shows that phenyl ring with negative electrostatic potential while pyrrolidine ring has slight positive electrostatic potential. Vibrational assignments, chemical shifts and geometrical parameters (bond lengths, bond angles, torsion angles) of PDP were calculated and found in good agreement with experimental results. The computed mass spectrum also exhibited important peaks including the base peak. PDP has higher anti-inflammatory activity 64.9 ± 2.2% at 50 mg/kg as compared to standard COX-1 inhibitor Ibuprofen 47±1.9%. The anticancer activity also exhibited significant inhibition of cancer for HT-29 cell line. The results imply the possible anti-inflammatory application of the compound beside some structural modifications may lead to establishing a new anticancer drug. Anti-inflammatory: 64.9 ± 2.2%, Ibuprofen= 47±1.9% (at 50 mg/kg) Anticancer: HCT-116 & HT-29 cell line (IC50:1.74±0.09 µM & 1.03±0.06 µM) Antioxidant: IC50 = 36.9 ± 2.3 μM [Display omitted]