Two adamantan-1-amine-based scaffolds: Synthesis, crystallographic synthons, TD/DFT calculations, in-depth molecular docking/ADME/T simulations, and shedding light on antibacterial/fungal activities

Majumdar, D and Elizabeth Philip, J and Tüzün, B and Sutradhar, D and Roy, S (2023) Two adamantan-1-amine-based scaffolds: Synthesis, crystallographic synthons, TD/DFT calculations, in-depth molecular docking/ADME/T simulations, and shedding light on antibacterial/fungal activities. In: Results in Chemistry, 6 .

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Abstract

This work synthesized and structurally characterized the two adamantan-1-amine-based compounds, C10H18N2O3 (1) and C21H23NO (2), reacting with adamantan-1-amine, copper nitrate and 2-hydroxy-1-napthaldehyde in methanol. 1 has a nitrate blue salt-like structure, while 2 has a yellow azomethine-bonded Schiff base. X-ray crystal structure divulges 1�2 crystallized orthorhombic (P212121) and monoclinic space groups (P21/c). In 1, the three nitrate O's form H bonds with three amine H from three different adamantylamine (N-H���O bonds), 2 adopts a keto-imine tautomeric form, shifting the -H from hydroxyl -O to imine -N. The crystal packing stability in 1 result from the coulombic energy between a cation (protonated amine) and an anion (nitrate), whereas in 2, dispersive energy dominates the crystal packing. Hirshfeld surfaces (HS) and 2D fingerprint plots visualize supramolecular contacts. DFT simulated IR/NMR spectrum and UV�vis in methanol were compared with experimental using TDDFT calculations. The AIM, NCI and HOMO-LUMO profiles substantiate the H-bonds classification. Espinosa's equation predicts that the H-bond strength for intra-molecular (2) and intermolecular (1) are �40.69 and �17.07 kJ/mol. The Fukui function, ESP, and NLO explore chemical reactivity locations and polarization characteristics. ADME/T prediction evaluates the drug-like properties. Molecular docking predicted antimicrobial potency against bacteria and fungus, confirmed further by experiments. © 2023 The Authors

Item Type:	Journal Article
Publication:	Results in Chemistry
Publisher:	Elsevier B.V.
Additional Information:	The copyright for this article belongs to authors.
Department/Centre:	Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited:	18 Nov 2024 21:14
Last Modified:	18 Nov 2024 21:14
URI:	http://eprints.iisc.ac.in/id/eprint/85328

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