Theoretical and experimental investigation of thiourea derivatives: synthesis, crystal structure, in-silico and in-vitro biological evaluation

Raza, Muhammad Asam; Sharif, A.A.; Danish, Muhammad; Rehman, Sadia; Budzianowski, Armand; Maurin, Jan K.

doi:10.4314/bcse.v35i3.10

Cited by 6 publications

(2 citation statements)

References 25 publications

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“…In MEP, plots were computed with different colors, which depicted the different behavior in terms of the potential of the molecule ( Figure 10 ). The order of the different colors in terms of charge distribution on the surfaces was red > orange > yellow > green > blue [ 38 ]. The nitrogen (red) depicted negative potential, while the hydrogen (blue) of alkyl and aromatic rings showed positive potential.…”

Section: Resultsmentioning

confidence: 99%

Bioassay-Guided Alkaloids Isolation from Camellia sinensis and Colchicum luteum: In Silico and In Vitro Evaluations for Protease Inhibition

et al. 2023

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Bioassay-guided isolation from Camellia sinensis (Theaceae) and Colchicum luteum (Liliaceae) utilizing an in vitro model of protease assay revealed colchicine (1) and caffeine (2) from chloroform fractions, respectively. Their structures were validated using spectral techniques. The purified compounds were further optimized with Gaussian software utilizing the B3LYP functional and 6-31G(d,p) basis set. The result files were utilized to determine several global reactivity characteristics to explain the diverse behavior of the compounds. Colchicine (1) showed a higher inhibition of protease activity (63.7 ± 0.5 %age with IC50 = 0.83 ± 0.07 mM), compared with caffeine (2) (39.2 ± 1.3 %age). In order to determine the type of inhibition, compound 1 was further studied, and, based on Lineweaver–Burk/Dixon plots and their secondary replots, it was depicted that compound 1 was a non-competitive inhibitor of this enzyme, with a Ki value of 0.690 ± 0.09 mM. To elucidate the theoretical features of protease inhibition, molecular docking studies were performed against serine protease (PDB #1S0Q), which demonstrated that compound 1 had a strong interaction with the different amino acid residues located on the active site of this understudied enzyme, with a high docking score of 16.2 kcal/mol.

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Section: Resultsmentioning

confidence: 99%

Bioassay-Guided Alkaloids Isolation from Camellia sinensis and Colchicum luteum: In Silico and In Vitro Evaluations for Protease Inhibition

et al. 2023

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“…Compounds that contain heteroatoms in their structure are of significant importance in either biological or industrial perspectives. Among heteroatoms, scientists have focused on molecules that contain an S atom and an N atom in their composition (Raza et al, 2021). The representative of this group of compounds is thiourea.…”

Section: Introductionmentioning

confidence: 99%

The pattern of bifurcated hydrogen bonds in thiourea cocrystals with diazine derivatives: experimental and quantum theoretical studies

Wzgarda-Raj,

Olszewski,

Palusiak

2024

Acta Crystallogr C Struct Chem

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Cocrystals of thiourea with pyrazine N-oxide as thiourea–pyrazine N-oxide (2/1), C4H4N2O·2CH4N2S, (I), and with phenazine as thiourea–phenazine (6/7), 7C12H8N2·6CH4N2S, (II), both crystallize in the monoclinic space group P21/c. In the crystalline state, molecules of both components are linked by N—H...N hydrogen bonds. In addition, there are R 2 2(8) hydrogen-bond synthons between thiourea molecules in both crystal structures. Furthermore, bifurcated hydrogen bonds between the –NH groups in the thiourea molecule and the N and O atoms in the N-oxide ring [in (I)], as well as the N atom in the central phenazine ring [in (II)], play a significant role in both structures. This emerging motif was thoroughly examined using quantum chemistry methods.

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Synthesis, spectral characteristics and molecular structure of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives

Pokotylo

Zadorozhnii

Kiselev

et al. 2023

Journal of Heterocyclic Chem

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In this work, we report the synthesis of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives based on acylated thioureas. The method for the preparation of 1,3,5‐oxadiazine derivatives is based on the reaction of dehydrosulfurization of the starting acylated thioureas under the action of dicyclohexylcarbodiimide (DCC) followed by the [4 + 2] cycloaddition reaction of another DCC molecule to the resulting intermediate carbodiimide. The structure of the obtained derivatives of 1,3,5‐oxadiazine was confirmed by 1H, 13C NMR, IR spectroscopy, mass spectrometry, and x‐ray diffraction analysis.

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Theoretical and experimental investigation of thiourea derivatives: synthesis, crystal structure, in-silico and in-vitro biological evaluation

Cited by 6 publications

References 25 publications

Bioassay-Guided Alkaloids Isolation from Camellia sinensis and Colchicum luteum: In Silico and In Vitro Evaluations for Protease Inhibition

Bioassay-Guided Alkaloids Isolation from Camellia sinensis and Colchicum luteum: In Silico and In Vitro Evaluations for Protease Inhibition

The pattern of bifurcated hydrogen bonds in thiourea cocrystals with diazine derivatives: experimental and quantum theoretical studies

Synthesis, spectral characteristics and molecular structure of 2H‐1,3,5‐oxadiazine‐2,4(3H)‐diimine derivatives

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