Structure investigation, spectral characterization, electronic properties, and antimicrobial and molecular docking studies of 3′‐(1‐benzyl‐5‐methyl‐1H‐1,2,3‐triazole‐4‐carbonyl)‐1′‐methyl‐4′‐phenyl‐2H‐spiro[acenaphthylene‐1,2′‐pyrrolidine]‐2‐one

Abstract

A new compound, 3′‐(1‐benzyl‐5‐methyl‐1H‐1,2,3‐triazole‐4‐carbonyl)‐1′‐methyl‐4′‐phenyl‐2H‐spiro[acenaphthylene‐1,2′‐pyrrolidin]‐2‐one (BTANP), was prepared, analyzed by Single Crystal X‐ray Diffraction (SCXRD), and investigated spectroscopically, which includes NMR, FT‐IR/Raman, UV–Vis, and fluorescence studies. All the computations have been made with the resource of density functional theory (DFT) (B3LYP/6‐311G [d,p]) and compared with the measured values. The vibrational assignments with potential energy distribution (PED) percentages were figured out using the VEDA4 program. The computed 1H‐NMR and 13C‐NMR chemical shifts were acquired using the gauge invariant atomic orbital (GIAO) technique and were contrasted with determined records. The computed electronic (NBO, NLO, HOMO‐LUMO, chemical reactivity descriptors) and thermodynamic properties were also scrutinized and elucidated. The BTANP was evaluated for antimicrobial activity toward few bacterial and fungal strains and was also compared with standard drugs. In addition, molecular docking mockups were executed on BTANP against topoisomerase II gyrase and human lanosterol 14 α‐demethylase enzymes.

Synthesis and Characterization of New Spirooxindoles Including Triazole and Benzimidazole Pharmacophores via [3+2] Cycloaddition Reaction: An MEDT Study of the Mechanism and Selectivity

“…In 2019, Malarkodi et al [10] synthesized and compared 3'- (1benzyl-5-methyl-1H-1,2,3-triazole-4carbonyl)-1'methyl-4'-phenyl-2H-spiro[acenaphthylene-1,2'-pyrrolidin]-2-one (BTANP) against a few bacterial and fungal strains as well as standard drugs. In addition, molecular docking mockups were developed on BTANP against topoisomerase II gyrase and human lanosterol 14 α demethylase enzymes [10].…”

“…In 2016, Rajeswari et al [9] developed an efficient, onepot, four-component condensation procedure for the synthesis of selective spirooxindolepyrrolizine-linked 1,2,3-triazole conjugates via a [3+2] cycloaddition (32CA) reaction using coumarin-3-carboxylic acid, N-propargylated isatin, L-proline/sarcosine, and aryl azides and using Cu(I) as a catalyst in the presence of glacial CH 3 COOH at 60 • C [9]. In 2019, Malarkodi et al [10] synthesized and compared 3'-(1-benzyl-5-methyl-1H-1,2,3-triazole-4carbonyl)-1'methyl-4'-phenyl-2H-spiro[acenaphthylene-1,2'-pyrrolidin]-2-one (BTANP) against a few bacterial and fungal strains as well as standard drugs. In addition, molecular docking mockups were developed on BTANP against topoisomerase II gyrase and human lanosterol 14 α demethylase enzymes [10].…”

Synthesis, crystal structure elucidation, DFT analysis, drug‐likeness and ADMET evaluation and molecular docking studies of triazole derivatives: Binary inhibition of spike protein and ACE2 receptor protein of COVID‐19

“…In triazole rings, the bond distances and bond angles of molecules A & B are found nearer to the reported values for analogous triazole derivatives. [ 40 , 41 ] The selected geometric parameters are provided in Table 2 .…”

Theoretical Investigation of para Amino-Dichloro Chalcone Isomers. Part II: A DFT Structure–Stability Study of the FMO and NLO Properties

“…Furthermore, they measured the hardness (η = 0.999), chemical potential (μ = −7.026), electronegativity (χ = 7.026), and electrophilicity index (ω = 24.707). Malarkodi et al 20 have analyzed the FMO characteristics of 3′-(1-benzyl-5-methyl-1 H -1,2,3-triazole-4-carbonyl)-1′-methyl-4′-phenyl-2 H -spiro-[acenaphthylene-1,2′-pyrrolidine]-2-one using DFT (B3LYP) with the 6-311G(d,p) basis set. They have found that this molecule has a small HOMO–LUMO energy gap of −3.4869 eV with large intramolecular charge transfer interactions, and therefore it is classified as a soft, highly polarizable, and reactive molecule.…”