Detailed structural study of cyclic anticancer drug Lorlatinib: spectroscopic and stereostructure investigation (IR, ECD and NMR) using density functional theory approach

Jiang, Shitian; Jin, Yingxue; Yan, Rui; Wang, Zhiqiang

doi:10.1016/j.molstruc.2020.129295

Cited by 8 publications

(15 citation statements)

References 35 publications

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“…The use of IR and NMR ( 1 H and 13 C) spectroscopy, nowadays coupled with theoretical computations, is proving to be an effective tool for analyzing the vibrational and chemical shifts within molecules. 17 The vibrational spectra, chemical shifts, and simulated outcomes can help to distinguish vibrational modes, chemical shifts (isotropic value), and structural features of the synthesized compounds. 18 Using density functional theory (DFT)/B3LYP methods with the B3LYP/6-311** basis set, we examined the vibrational spectra and chemical shift (isotropic value).…”

Section: Resultsmentioning

confidence: 99%

“… 18 Using density functional theory (DFT)/B3LYP methods with the B3LYP/6-311** basis set, we examined the vibrational spectra and chemical shift (isotropic value). 17 , 18 First, conformational search of compound 14 was first performed using the OPLS-2005 method. Consequently, the conformers were reoptimized by applying DFT at the B3LYP/6-311** level.…”

Section: Resultsmentioning

confidence: 99%

“…Aromatic hydrogen atoms tend to appear in high-field regions, and aliphatic hydrogen atoms appear in low-field regions; with an increased electron cloud density, electronegative groups can increase the chemical shift. 17 − 20…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents

et al. 2022

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The condensation of phthalic anhydride afforded structurally modified isoindoline-1,3-dione derivatives with selected amino-containing compounds. The title compounds ( 2 – 30 ) have been characterized by thin-layer chromatography (TLC), infrared spectroscopy, 1 H and 13 C NMR spectroscopy, and mass spectroscopy. All of the compounds were assessed for their antimycobacterial activity toward the H37Rv strain by a dual read-out assay method. Among the synthesized compounds, compound 27 possessed a significant IC 50 of 18 μM, making it the most potent compound of the series. The InhA inhibitory (IC 50 ) activity of compound 27 was 8.65 μM in comparison to Triclosan (1.32 μM). Computational studies like density functional theory (DFT) study, molecular docking, and dynamic simulation studies illustrated the reactivity and stability of the synthesized compounds as InhA inhibitors. A quantum-mechanics-based DFT study was carried out to investigate the molecular and electronic properties, reactivities, and nature of bonding present in the synthesized compounds and theoretical vibrational (IR) and isotropic value ( 1 H and 13 C NMR) calculations.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents

et al. 2022

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“…Electrophilicity index predicts the stabilization energy when its electrons are saturated and can even be used to predict biological activity. According to Jiang et al [ 14 ] the global reactivity descriptors (a.u.) of lorlatinib are 0.21794 (ionization potential), 0.06768 (electron affinity), ‐0.14281 (chemical potential), 0.07513 (hardness) and 0.27146 (electrophilicity index).…”

Section: Resultsmentioning

confidence: 99%

“…[ 13 ] Jiang et al published a structural analysis of the cyclic anticancer drug lorlatinib. [ 14 ] The structural investigations, density functional theory (DFT) studies on selpercatinib and IR spectroscopy with DFT studies of erlotinib were reported. [ 15,16 ] Due to the anti‐cancerous activity of lorlatinib (LTB), the reactivity analysis together with AIM and MD simulations are reported.…”

Section: Introductionmentioning

confidence: 99%

Investigations into the electronic properties of lorlatinib, an anti‐cancerous drug using DFT, wavefunction analysis and MD simulations

Al‐Otaibi,

Mary,

Mary

et al. 2022

Vietnam Journal of Chemistry

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Lung cancer is a kind of cancer with high morbidity and mortality rate, making it one of the most dangerous tumors to humanity's health and existence. Wavefunction dependent reactivity analysis, atom in molecule (AIM) and molecular dynamics (MD) simulations of lorlatinib (LTB) are reported in the present work. Electrophilicity index predicts the biological activity. The bond ellipticity describes the anisotropy of the curvature of electron density and its maximum value is at C15‐H32. Chemical environments, N8 = C26‐N7, C18 = C30 ≡ N9, and C15 = C14‐C13 are found to be highest delocalization regions. The complexes were stable throughout the simulation and amino acids involved in bringing the overall structural deviation are explored.

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Synthesis, spectroscopic, topological, hirshfeld surface analysis, and anti-covid-19 molecular docking investigation of isopropyl 1-benzoyl-4-(benzoyloxy)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Ramalingam

Murugavel²,

Sambandam

et al. 2022

Heliyon

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Detailed structural study of cyclic anticancer drug Lorlatinib: spectroscopic and stereostructure investigation (IR, ECD and NMR) using density functional theory approach

Cited by 8 publications

References 35 publications

Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents

Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents

Investigations into the electronic properties of lorlatinib, an anti‐cancerous drug using DFT, wavefunction analysis and MD simulations

Synthesis, spectroscopic, topological, hirshfeld surface analysis, and anti-covid-19 molecular docking investigation of isopropyl 1-benzoyl-4-(benzoyloxy)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

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