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
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...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-12-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715623004678 |
| _version_ | 1797398618053804032 |
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| author | Dhrubajyoti Majumdar Jessica Elizabeth Philip Burak Tüzün Dipankar Sutradhar Sourav Roy |
| author_facet | Dhrubajyoti Majumdar Jessica Elizabeth Philip Burak Tüzün Dipankar Sutradhar Sourav Roy |
| author_sort | Dhrubajyoti Majumdar |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-09T01:28:09Z |
| format | Article |
| id | doaj.art-3a157d27c22c405fbf1aa55b135a7db7 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-03-09T01:28:09Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-3a157d27c22c405fbf1aa55b135a7db72023-12-10T06:15:41ZengElsevierResults in Chemistry2211-71562023-12-016101228Two adamantan-1-amine-based scaffolds: Synthesis, crystallographic synthons, TD/DFT calculations, in-depth molecular docking/ADME/T simulations, and shedding light on antibacterial/fungal activitiesDhrubajyoti Majumdar0Jessica Elizabeth Philip1Burak Tüzün2Dipankar Sutradhar3Sourav Roy4Department of Chemistry, Tamralipta Mahavidyalaya, Tamluk 721636, West Bengal, India; Corresponding authors.Department of Chemistry, Alphonsa College, Palai, Kottayam, Kerala 686574, IndiaSivas Cumhuriyet University, Sivas Vocational School, Department of Plant and Animal Production, TR-58140 Sivas, TurkeySchool of Advanced Sciences and Languages, VIT Bhopal University, Bhopal 466114, Madhya Pradesh, IndiaSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India; Corresponding authors.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.http://www.sciencedirect.com/science/article/pii/S2211715623004678Adamantan-1-amineDFTAIM/NCIDockingADME/TAntibacterial/Fungal |
| spellingShingle | Dhrubajyoti Majumdar Jessica Elizabeth Philip Burak Tüzün Dipankar Sutradhar Sourav Roy 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 Results in Chemistry Adamantan-1-amine DFT AIM/NCI Docking ADME/T Antibacterial/Fungal |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | Adamantan-1-amine DFT AIM/NCI Docking ADME/T Antibacterial/Fungal |
| url | http://www.sciencedirect.com/science/article/pii/S2211715623004678 |
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