Usage of Quantum Chemical Methods to Understand the Formation of Concomitant Polymorphs of Acetyl 2-(<i>N</i>-(2-Fluorophenyl)imino)coumarin-3-carboxamide

Shishkina, Svitlana V.; Baumer, V. N.; Kovalenko, Sergiy M.; Trostianko, Pavel V.; Bunyatyan, N. D.

doi:10.1021/acsomega.0c05516

Cited by 6 publications

(12 citation statements)

References 57 publications

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“…The polymorphic forms I and II have the same packing type (columnar-layered), and the packing of DBUs is more anisotropic in the most stable polymorph I . The obtained regularities between crystal structure stability and the degree of its packing anisotropy correlate with previously published data. , …”

Section: Resultssupporting

confidence: 89%

“…The obtained regularities between crystal structure stability and the degree of its packing anisotropy correlate with previously published data. 35 , 36 …”

Section: Resultsmentioning

confidence: 99%

“…The obtained regularities between crystal structure stability and the degree of its packing anisotropy correlate with previously published data. 35,36 It should be also noted that the main difference of the polymorphic structure I in comparison to structure II is the absence or presence of stacking interactions between dimethylphenyl groups (Figure 7). The relative positions of the dimeric building units are very similar in these structures.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Quantum Chemical Study on Mefenamic Acid Polymorphic Forms

et al. 2022

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Three polymorphic structures of mefenamic acid, which is a very popular drug, have been studied using quantum chemical methods. It has been shown that the centrosymmetric dimer formed due to two O–H···O hydrogen bonds is a complex building unit in all of the polymorphic structures under study. On the basis of an analysis of the pairwise interaction energies between molecules, the polymorphic forms I and II are classified as columnar-layered while the polymorphic form III has a columnar structure. The stabilities of the three polymorphic forms of mefenamic acid under ambient conditions ( I > II > III ) correlate with the degree of anisotropy of the interaction energies between columns (primary basic structural motifs) formed due to stacking interactions. The shear deformation modeling of strongly bound layers in all of the polymorphic structures has not revealed any possibility for deformation of the crystal structure. The construction of the shift energy profiles and calculation of the energy barriers for the displacement along the (100) crystallographic plane in the [100], [010], and [011] crystallographic directions make it possible to explain the experimental data obtained for commercially available polymorphic structure I in a diamond anvil cell. The absence of any local minimum near the starting point on the shift energy profile and the extremely high energy barrier can be considered as criteria for the impossibility of a crystal structure deformation under pressure.

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Section: Resultssupporting

confidence: 89%

“…The obtained regularities between crystal structure stability and the degree of its packing anisotropy correlate with previously published data. 35 , 36 …”

Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Quantum Chemical Study on Mefenamic Acid Polymorphic Forms

et al. 2022

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“…Based on our earlier data, , such interactions of a basic molecule with its environment allow presuming that the polymorphic form 6MU_II is the most stable in comparison with other studied forms. The calculations of the lattice energies in periodic approximation for all of the polymorphic forms under study have revealed that polymorph 6MU_II has the lowest lattice energy.…”

Section: Resultsmentioning

confidence: 99%

New Polymorphic Modifications of 6-Methyluracil: An Experimental and Quantum Chemical Study

et al. 2023

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Polymorphism of 6-methyluracil, which affects the regulation of lipid peroxidation and wound healing, has been studied by experimental and quantum chemical methods. Two known polymorphic modifications and two new crystalline forms were crystallized and characterized by single crystal and powder X-ray diffraction (XRD) methods as well as by the differential scanning calorimetry (DSC) method and infrared (IR) spectroscopy. The calculations of pairwise interaction energies between molecules and lattice energies in periodic boundary conditions have shown that the polymorphic form 6MU_I used in the pharmaceutical industry and two new forms 6MU_III and 6MU_IV, which can be formed due to temperature violations, may be considered as metastable. The centrosymmetric dimer bound by two N–H···O hydrogen bonds was recognized as a dimeric building unit in all of the polymorphic forms of 6-methyluracil. Four polymorphic forms have a layered structure from the viewpoint of interaction energies between dimeric building units. The layers parallel to the (100) crystallographic plane were recognized as a basic structural motif in the 6MU_I, 6MU_III, and 6MU_IV crystals. In the 6MU_II structure, a basic structural motif is a layer parallel to the (001) crystallographic plane. The ratio between the interaction energies within the basic structural motif and between neighboring layers correlates with the relative stability of the studied polymorphic forms. The most stable polymorphic form 6MU_II has the most anisotropic “energetic” structure, while the interaction energies in the least stable form 6MU_IV are very close in various directions. The modeling of shear deformations of layers in the metastable polymorphic structures has not revealed any possibility of these crystals to be deformed under external mechanical stress or pressure influence. These results allow the use of metastable polymorphic forms of 6-methyluracil in the pharmaceutical industry without any limitations.

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“…Several compounds with a central 2-iminocoumarin (2-imino-2 H -chromene)—less known coumarin analogs—are studied for many interesting potential applications due to their optical or fluorescent properties [ 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ]. Furthermore, it was found that compounds bearing 2-iminocoumarin core possess antimicrobial [ 53 , 54 , 55 ] and anti-inflammatory [ 56 ] activities, or neuroprotective properties, such as BACE1 inhibitors [ 57 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure and Cytotoxic Properties of Copper(II) Complexes of 2-Iminocoumarins Bearing a 1,3,5-Triazine or Benzoxazole/Benzothiazole Moiety

et al. 2022

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A series of copper(II) complexes of 2-imino-2H-chromen-3-yl-1,3,5-triazines 2a-h, 3-(benzoxazol-2-yl)-2H-chromen-2-imines 4a-b, and 3-(benzothiazol-2-yl)-2H-chromen-2-imines 6a-c were obtained by reacting of appropriate 2-iminocoumarin ligands L1a-h, L3a-b, and L5a-c with 3-fold molar excess of copper(II) chloride. The structure of these compounds was confirmed by IR spectroscopy, elemental analysis, and single-crystal X-ray diffraction data (2f, 2g, 2h, and 6c). All the synthesized complexes were screened for their activity against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO, and RT-4 by using a crystal violet microtiter plate assay and relationships between structure and in vitro cytotoxic activity are discussed. The coordination of 2-iminocoumarins with copper(II) ions resulted in complexes 2a-h, 4a-b, and 6a-c with significant inhibitory properties toward tested tumor cell lines with IC50 values ranging from 0.04 μM to 15.66 μM. In comparison to the free ligands L1a-h, L3a-b, and L5a-c, the newly prepared Cu(II) complexes often displayed increased activity. In the series of copper(II) complexes of 2-imino-2H-chromen-3-yl-1,3,5-triazines 2a-h the most potent compound 2g contained a 4-phenylpiperazine moiety at position 6 of the 1,3,5-triazine ring and an electron-donating diethylamino group at position 7′ of the 2-iminocoumarin scaffold. Among the Cu(II) complexes of 3-(benzoxazol-2-yl)-2H-chromen-2-imines 4a-b and 3-(benzothiazol-2-yl)-2H-chromen-2-imines 6a-c the most active was benzoxazole-2-iminocoumarin 4b that also possessed a diethylamino group at position 7′ of the 2-iminocoumarin moiety. Moreover, compound 4b was found to be the most prominent agent and displayed the higher potency than cisplatin against tested cell lines.

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Usage of Quantum Chemical Methods to Understand the Formation of Concomitant Polymorphs of Acetyl 2-(N-(2-Fluorophenyl)imino)coumarin-3-carboxamide

Cited by 6 publications

References 57 publications

Quantum Chemical Study on Mefenamic Acid Polymorphic Forms

Quantum Chemical Study on Mefenamic Acid Polymorphic Forms

New Polymorphic Modifications of 6-Methyluracil: An Experimental and Quantum Chemical Study

Synthesis, Structure and Cytotoxic Properties of Copper(II) Complexes of 2-Iminocoumarins Bearing a 1,3,5-Triazine or Benzoxazole/Benzothiazole Moiety

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