Experimental and Theoretical Quantum Chemical Studies of 2-(2-acetamidophenyl)-2-oxo-N-(pyridin-2-ylmethyl)acetamide and Its Copper(II) Complex: Molecular Docking Simulation of the Designed Coordinated Ligand with Insulin-like Growth Factor-1...

Overview

Journal BMC Chem

Publisher Springer Nature

Specialty Chemistry

Date 2024 Jun 13

PMID 38872213

Authors

Doaa S El-Sayed

Leena Sinha

Amina A Soayed

Affiliations

Soon will be listed here.

Abstract

Newly synthesized ligand 2-(2- acetamidophenyl)-2-oxo-N-(pyridin-2-ylmethyl)acetamide and its copper(II) complex were characterized by elemental analyses, FT-IR, UV-Vis., ESR, H-NMR, and thermal analysis along with the theoretical quantum chemical studies. Combined experimental and theoretical DFT (density functional theory) studies showed the ligand to be a tridentate ligand with three coordinate bonds. The complex was suggested to be in a distorted octahedral structure with d ground state. The activation energy, ΔE; entropy ΔS; enthalpy ΔH and order of reaction has been derived from differential thermogravimetric (DTA) curve, using Horowitz-Metzeger method. The nujol mull electronic spectrum of the ligand and Cu(II) complex have been recorded and the difference of the excited and ground state densities has also been theoretically calculated and plotted to investigate the movement of electrons on excitation. The Cu(II) complex was evaluated for its antibacterial activity against two bacterial species, namely Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus). Antifungal screening was performed against two species (Condida albicans and Aspergillus flavus). The complex under investigation was found to possess notable biological activity. Molecular docking investigation predicted different types of non-covalent interactions of the synthesized ligand towards Insulin-like growth factor 1 receptor (ID: 5FXR).

Citing Articles

Structural and topological analysis of thiosemicarbazone-based metal complexes: computational and experimental study of bacterial biofilm inhibition and antioxidant activity.

El-Sayed D, Hassan S, Jassim L, Issa A, Al-Oqaili F, Albayaty M BMC Chem. 2025; 19(1):24.

PMID: 39856776 PMC: 11762858. DOI: 10.1186/s13065-024-01338-5.

References

Constable E . 2,2':6',2''-terpyridines: from chemical obscurity to common supramolecular motifs. Chem Soc Rev. 2007; 36(2):246-53. DOI: 10.1039/b601166g. View

Antonioli B, Buchner B, Clegg J, Gloe K, Gloe K, Gotzke L . Interaction of an extended series of N-substituted di(2-picolyl)amine derivatives with copper(II). Synthetic, structural, magnetic and solution studies. Dalton Trans. 2009; (24):4795-805. DOI: 10.1039/b901832h. View

Turba S, Walter O, Schindler S, Nielsen L, Hazell A, McKenzie C . Syntheses, structures, and properties of copper(II) complexes of bis(2-pyridylmethyl) derivatives of o-, m-, and p-phenylenediamine and aniline. Inorg Chem. 2008; 47(20):9612-23. DOI: 10.1021/ic800244g. View

Kunishita A, Scanlon J, Ishimaru H, Honda K, Ogura T, Suzuki M . Reactions of copper(II)-H2O2 adducts supported by tridentate bis(2-pyridylmethyl)amine ligands: sensitivity to solvent and variations in ligand substitution. Inorg Chem. 2008; 47(18):8222-32. DOI: 10.1021/ic800845h. View

Fouad R, Shaaban I, Ali T, Assiri M, Shenouda S . Co(ii), Ni(ii), Cu(ii) and Cd(ii)-thiocarbonohydrazone complexes: spectroscopic, DFT, thermal, and electrical conductivity studies. RSC Adv. 2022; 11(60):37726-37743. PMC: 9043744. DOI: 10.1039/d1ra06902k. View

Sayed D, Abdelrehim E . Spectroscopic details on the molecular structure of pyrimidine‑2‑thiones heterocyclic compounds: computational and antiviral activity against the main protease enzyme of SARS-CoV-2. BMC Chem. 2022; 16(1):82. PMC: 9628048. DOI: 10.1186/s13065-022-00881-3. View

Idemudia O, Sadimenko A, Hosten E . Metal Complexes of New Bioactive Pyrazolone Phenylhydrazones; Crystal Structure of 4-Acetyl-3-methyl-1-phenyl-2-pyrazoline-5-one phenylhydrazone Ampp-Ph. Int J Mol Sci. 2016; 17(5). PMC: 4881513. DOI: 10.3390/ijms17050687. View

Visser H, Dube C, Armstrong W, Sauer K, Yachandra V . FTIR spectra and normal-mode analysis of a tetranuclear manganese adamantane-like complex in two electrochemically prepared oxidation states: relevance to the oxygen-evolving complex of photosystem II. J Am Chem Soc. 2002; 124(37):11008-17. PMC: 3965206. DOI: 10.1021/ja020409j. View

Lucchese B, Humphreys K, Lee D, Incarvito C, Sommer R, Rheingold A . Mono-, bi-, and trinuclear CuII-Cl containing products based on the tris(2-pyridylmethyl)amine chelate derived from copper(I) complex dechlorination reactions of chloroform. Inorg Chem. 2004; 43(19):5987-98. DOI: 10.1021/ic0497477. View

10.

Yusuf T, Oladipo S, Zamisa S, Kumalo H, Lawal I, Lawal M . Design of New Schiff-Base Copper(II) Complexes: Synthesis, Crystal Structures, DFT Study, and Binding Potency toward Cytochrome P450 3A4. ACS Omega. 2021; 6(21):13704-13718. PMC: 8173565. DOI: 10.1021/acsomega.1c00906. View

11.

Pfaller M, Burmeister L, Bartlett M, Rinaldi M . Multicenter evaluation of four methods of yeast inoculum preparation. J Clin Microbiol. 1988; 26(8):1437-41. PMC: 266638. DOI: 10.1128/jcm.26.8.1437-1441.1988. View

12.

Pahontu E, Ilies D, Shova S, Paraschivescu C, Badea M, Gulea A . Synthesis, characterization, crystal structure and antimicrobial activity of copper(II) complexes with the Schiff base derived from 2-hydroxy-4-methoxybenzaldehyde. Molecules. 2015; 20(4):5771-92. PMC: 6272500. DOI: 10.3390/molecules20045771. View

13.

Sugai Y, Fujii S, Fujimoto T, Yano S, Mikata Y . Asymmetric sulfur atom coordination in a copper(II) dipicolylamine (DPA) complex with a thioglycoside ligand. Dalton Trans. 2007; (33):3705-9. DOI: 10.1039/b706423c. View

14.

BAUER A, KIRBY W, SHERRIS J, Turck M . Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol. 1966; 45(4):493-6. View

15.

Sayed D, Abdelrehim E . Computational details of molecular structure, spectroscopic properties, topological studies and SARS-Cov-2 enzyme molecular docking simulation of substituted triazolo pyrimidine thione heterocycles. Spectrochim Acta A Mol Biomol Spectrosc. 2021; 261:120006. PMC: 8149157. DOI: 10.1016/j.saa.2021.120006. View

16.

Abdelrehim E, El-Sayed D . Synthesis, screening as potential antitumor of new poly heterocyclic compounds based on pyrimidine-2-thiones. BMC Chem. 2022; 16(1):16. PMC: 8939104. DOI: 10.1186/s13065-022-00810-4. View

17.

Lee , Yang , PARR . Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B Condens Matter. 1988; 37(2):785-789. DOI: 10.1103/physrevb.37.785. View

18.

Morris G, Huey R, Lindstrom W, Sanner M, Belew R, Goodsell D . AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem. 2009; 30(16):2785-91. PMC: 2760638. DOI: 10.1002/jcc.21256. View

19.

El-Faham A, Khattab S, Ghabbour H, Fun H, Siddiqui M . Microwave irradiation: synthesis and characterization of α-ketoamide and bis (α-ketoamide) derivatives via the ring opening of -acetylisatin. Chem Cent J. 2014; 8(1):27. PMC: 4021159. DOI: 10.1186/1752-153X-8-27. View

20.

Nkungli N, Tamafo Fouegue A, Tasheh S, Bine F, Hassan A, Ghogomu J . In silico investigation of falcipain-2 inhibition by hybrid benzimidazole-thiosemicarbazone antiplasmodial agents: A molecular docking, molecular dynamics simulation, and kinetics study. Mol Divers. 2023; 28(2):475-496. PMC: 9838286. DOI: 10.1007/s11030-022-10594-3. View