Synthesis of new N-alkylated 6-bromoindoline-2.3-dione derivatives: Crystal structures, spectroscopic characterizations, Hirschfeld surface analyses, molecular docking studies, DFT calculations, and antibacterial activity

被引:4
作者
Rharmili, Nohaila [1 ]
Sert, Yusuf [2 ]
Rodi, Youssef Kandri [1 ]
Chahdi, Fouad Ouazzani [1 ]
Haoudi, Amal [1 ]
Mague, Joel T. [3 ]
Mazzah, Ahmed [4 ]
El Hachlafi, Naoufal [5 ]
Benkhaira, Nesrine [5 ]
Fikri-Benbrahim, Kawtar [5 ]
Essassi, El Mokhtar [6 ]
Sebbar, Nada Kheira [7 ,8 ]
机构
[1] Sidi Mohamed Ben Abdellah Univ, Fac Sci & Tech, Lab Appl Organ Chem, BP 2202, Fes 30050, Morocco
[2] Bozok Univ, Dept Phys, Yozgat, Turkiye
[3] Tulane Univ, Dept Chem, New Orleans, LA 70118 USA
[4] Univ Lille, CNRS, USR 3290, MSAP,Miniaturisat Synth Anal & Prote, F-59000 Lille, France
[5] Sidi Mohamed Ben Abdellah Univ, Sci & Technol Fac, Microbial Biotechnol & Bioact Mol Lab, Fes, Morocco
[6] Mohammed V Univ Rabat, Fac Sci Ave Ibn Battouta, Lab Heterocycl Organ Chem, BP 1014, Rabat, Morocco
[7] Ibnou Zohr Univ, Fac Sci, Lab Organ & Phys Chem, Appl Bioorgan Chem Team, Agadir, Morocco
[8] Mohammed V Univ Rabat, Fac Sci, Lab Plant Chem Organ & Bioorgan Synth, Rabat, Morocco
关键词
6-bromoisatin; Alkylation; X-ray diffraction; DFT; Hirshfeld surface; Molecular docking; TYRIAN PURPLE; ISATIN; ANTICANCER; INDOLES;
D O I
10.1016/j.rechem.2024.101338
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ten new isatin derivatives (2-11) were synthesized by alkylation reactions under phase transfer catalysis (PTC) conditions. Structural characterization of all compounds was performed using 1H and 13C NMR spectroscopy. The molecular and crystal structures of three compounds (4, 7, and 8) were confirmed through single -crystal X-ray diffraction analysis. Spectral data were also calculated using density function theory (DFT) at the B3LYP/ 6-311++G(d, p) level and compared to the experimental results, to understand the non -binding intermolecular interactions in the solid phase crystal packing. The closest contacts between atoms of the three molecules studied were identified by 2D and 3D Hirshfeld surface analyses. The structures of 4, 7 and 8 are optimized and their HOMO and LUMO energies, as well as their orbital pictures were evaluated. The experimental results correlated well with the calculated results. Finally, molecular docking studies of 4, 7 and 8 were performed to investigate their binding patterns with inhibitory targets from the Protein Data Bank (PDB: 3G7B and PDB: 3T0T using the AutoDock Vina program. The antibacterial activities of 2-11 against Gram-positive and Gram-negative microbial strains, such as Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa were evaluated, and the findings indicated that 4 and 8 exhibited the highest efficacy, as reflected in their minimal inhibitory concentration (MIC) values.
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页数:12
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