Conformational flexibility and packing plausibility of repaglinide polymorphs

Rani, Dimpy; Goyal, Parnika; Chadha, Renu

doi:10.1016/j.molstruc.2017.12.036

Cited by 4 publications

(2 citation statements)

References 6 publications

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“…The Finasteride form I [ 39 ] and Repaglinide form I [ 40 ] were obtained by recrystallization from absolute ethanol by means of the slow evaporation method and ethanol/water (2:1) by the solvent–antisolvent method, respectively. The received samples were dried under vacuum for 48 h at 313 K.…”

Section: Methodsmentioning

confidence: 99%

Harmonic Vibrational Frequency Simulation of Pharmaceutical Molecules via a Novel Multi-Molecular Fragment Interception Method

Wang¹,

Zhang²,

Yang³

et al. 2023

Molecules

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By means of a computational method based on Density Functional Theory (DFT), using commercially available software, a novel method for simulating equilibrium geometry harmonic vibrational frequencies is proposed. Finasteride, Lamivudine, and Repaglinide were selected as model molecules to study the adaptability of the new method. Three molecular models, namely the single-molecular, central-molecular, and multi-molecular fragment models, were constructed and calculated by Generalized Gradient Approximations (GGAs) with the PBE functional via the Material Studio 8.0 program. Theoretical vibrational frequencies were assigned and compared to the corresponding experimental data. The results indicated that the traditional single-molecular calculation and scaled spectra with scale factor exhibited the worst similarity for all three pharmaceutical molecules among the three models. Furthermore, the central-molecular model with a configuration closer to the empirical structure resulted in a reduction of mean absolute error (MAE) and root mean squared error (RMSE) in all three pharmaceutics, including the hydrogen-bonded functional groups. However, the improvement in computational accuracy for different drug molecules using the central-molecular model for vibrational frequency calculation was unstable. Whereas, the new multi-molecular fragment interception method showed the best agreement with experimental results, exhibiting MAE and RMSE values of 8.21 cm−1 and 18.35 cm−1 for Finasteride, 15.95 cm−1 and 26.46 cm−1 for Lamivudine, and 12.10 cm−1 and 25.82 cm−1 for Repaglinide. Additionally, this work provides comprehensive vibrational frequency calculations and assignments for Finasteride, Lamivudine, and Repaglinide, which have never been thoroughly investigated in previous research.

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Section: Methodsmentioning

confidence: 99%

Harmonic Vibrational Frequency Simulation of Pharmaceutical Molecules via a Novel Multi-Molecular Fragment Interception Method

Wang¹,

Zhang²,

Yang³

et al. 2023

Molecules

View full text Add to dashboard Cite

show abstract

“…Polymorphism is literally defined as having several shapes or the existence of a material in several crystalline forms. In other words, it indicates the existence of a chemical substance in more than one crystalline form with similar characteristics . In recent years, polymorphism in chemistry has turned out to be an interestingly strange and unusual phenomenon worthy of being developed in the related studies, especially in the industrial and academic communities .…”

Section: Introductionmentioning

confidence: 99%

Polymorphism of Palladium(II) Complexes : Crystal Structure Determination, Luminescence Properties, Hirshfeld Surface Analyses and DFT/TD‐DFT Studies

et al. 2019

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Two luminescent polymorphs based on a new Pd(II) complex [Pd(mtzt)2(en)] (mtzt=1‐methyl‐1H‐1,2,3,4‐tetrazole‐5‐thiol and en=ethylenediamine) have been synthesized and characterized by FTIR, UV/Vis, elemental analysis,1HNMR and single‐crystal X‐ray diﬀraction analysis. The X‐ray structural analysis indicated that in the structures of these polymorphs Pd(II) cation is four‐coordinated in a distorted square planer configuration by two tetrazole rings in the cis‐positions, two nitrogen atoms of chelated ethylenediamine ligand. The dihedral angles between the planes of the tetrazole rings of polymorphs (1) and (2) are 72.01 and 77.70°, respectively. Moreover, in these polymorphs, intermolecular interactions C−H…N, C−H…S, and N−H…N hydrogen bonds, are effective in the stabilization of the crystal structures. The present study reports a detailed analysis of Hirshfeld surfaces, facilitating a comparison of intermolecular interactions in the supramolecular structure. The geometries of polymorphs (1) and (2) are optimized with B3LYP−D3/TZVP method, and analyzed with natural bond orbital (NBO), then their UV/Vis spectra are calculated with time‐dependent density functional theory (TD‐DFT) method. The IR spectroscopy was performed using VEDA4 software and compared with the experimental values. Quantum chemical parameters are: such as EHOMO, ELUMO, energy gap, chemical hardness (η), and dipole moment (μ), and the frontier molecular orbital properties.

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The first insight into the supramolecular structures of popular drug repaglinide: Focus on intermolecular interactions in antidiabetic agents

Bojarska

Fruziński

Sieroń

et al. 2019

Journal of Molecular Structure

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Conformational flexibility and packing plausibility of repaglinide polymorphs

Cited by 4 publications

References 6 publications

Harmonic Vibrational Frequency Simulation of Pharmaceutical Molecules via a Novel Multi-Molecular Fragment Interception Method

Harmonic Vibrational Frequency Simulation of Pharmaceutical Molecules via a Novel Multi-Molecular Fragment Interception Method

Polymorphism of Palladium(II) Complexes : Crystal Structure Determination, Luminescence Properties, Hirshfeld Surface Analyses and DFT/TD‐DFT Studies

The first insight into the supramolecular structures of popular drug repaglinide: Focus on intermolecular interactions in antidiabetic agents

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