π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

Baykov, Sergey V.; Mikherdov, Alexander S.; Novikov, Alexander S.; Geyl, Kirill K.; Tarasenko, M. V.; Boyarskiy, Vadim P.

doi:10.3390/molecules26185672

Cited by 42 publications

(19 citation statements)

References 93 publications

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“…It should be mentioned that stacking interactions between heterocycles and the aromatic amino acid side chains Phe, Tyr, and Trp are a very attractive topic [ 56 ] in the frame of medicinal chemistry owing to the fact that heterocyclic scaffolds prevail between drugs in the market [ 57 , 58 , 59 , 60 ]. Boyarskiy et al [ 61 ] gave a detailed analysis of the π–π noncovalent interaction involving an oxadiazole system.…”

Section: Resultsmentioning

confidence: 99%

Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation

et al. 2022

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Herein, we report computational and experimental evaluations of the antimicrobial activity of twenty one 2,3-diaryl-thiazolidin-4-ones. All synthesized compounds exhibited an antibacterial activity against six Gram-positive and Gram-negative bacteria to different extents. Thus, the MIC was in the range of 0.008–0.24 mg/mL, while the MBC was 0.0016–0.48 mg/mL. The most sensitive bacterium was S. Typhimurium, whereas S. aureus was the most resistant. The best antibacterial activity was observed for compound 5 (MIC at 0.008–0.06 mg/mL). The three most active compounds 5, 8, and 15, as well as compound 6, which were evaluated against three resistant strains, MRSA, P. aeruginosa, and E. coli, were more potent against all bacterial strains used than ampicillin. The antifungal activity of some compounds exceeded or were equipotent with those of the reference antifungal agents bifonazole and ketoconazole. The best activity was expressed by compound 5. All compounds exhibited moderate to good drug-likeness scores ranging from −0.39 to 0.39. The docking studies indicated a probable involvement of E.coli Mur B inhibition in the antibacterial action, while CYP51 inhibition is likely responsible for the antifungal activity of the tested compounds. Finally, the assessment of cellular cytotoxicity of the compounds in normal human MRC-5 cells revealed that the compounds were not toxic.

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Section: Resultsmentioning

confidence: 99%

Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation

et al. 2022

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“…Now a convenient method for the synthesis of N,Ndialkyl-N'-pyridin-2-yl-substituted ureas as a result of one-step activation of the CÀ H bond in pyridine-Noxides has been developed in our research group. [70][71][72][73] In further study, we demonstrated that these pyridylureas can be converted to N-pyridylcarbamates via heating with an excess of corresponding alcohols [74] (Scheme 1). According to our study, this process occurred via isocyanate intermediate formation and it motivated us to extend this reaction to N-nucleophiles.…”

Section: Introductionmentioning

confidence: 96%

“…Now a convenient method for the synthesis of N , N ‐dialkyl‐ N‘ ‐pyridin‐2‐yl‐substituted ureas as a result of one‐step activation of the C−H bond in pyridine‐ N ‐oxides has been developed in our research group [70–73] . In further study, we demonstrated that these pyridylureas can be converted to N ‐pyridylcarbamates via heating with an excess of corresponding alcohols [74] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents

et al. 2022

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A protocol for the synthesis of unsymmetrical ureas substituted by pyridyl/quinolinyl moiety has been developed. This method concluded in metal‐ and base‐free reamination of N,N‐dimethyl‐N‘‐hetaryl ureas with a wide range of aryl and alkyl amines. The isolated yields vary from 40 to 96% depending on the nucleophilicity of the amines. The scope of this method includes more than 50 examples. The reaction is not hindered by either donor or acceptor groups as well as diverse functionalities. The synthesis can be easily scaled to gram quantities. Theoretical calculations supported by experimental data allowed us to propose a plausible mechanism for the process. This reaction takes place through the intermediate formation of hetaryl isocyanate.

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“…The structure and reactivity (including coordination with Pt(II)) of these compounds were studied [ 36 , 37 , 38 ]. In the present study we employed N , N -dialkyl- N ′-(pyridin-2-yl)-ureas, thus obtained, to synthesize novel Cu(II) complexes in the context of the global drug discovery efforts for metal-based tumor-suppressing agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, and Antiproliferative Action of 2-Pyridyl Urea-Based Cu(II) Complexes

et al. 2022

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Relying on a recently suggested protocol that furnishes convenient access to variously substituted 2-pyridyl ureas, twelve hitherto unknown Cu(II) complexes have been synthesized in the present work and their structures were evaluated by elemental analysis, HRMS, IR spectroscopy, and X-ray diffraction study. Two structural motifs ([Cu(L)2Cl]+[Cl]− or (Cu(L)2Cl2) depending on the substitution pattern on the 2-pyridine fragment were revealed. In addition, antiproliferative action of the obtained compounds have been investigated against lung cancer cell lines (A549, NCI-H460, NCI-H1975), and healthy WI-26 VA4 cells were used to monitor non-specific cytotoxicity. Two nitro-group substituted complexes Cu(U3)2Cl2 (IC50 = 39.6 ± 4.5 μM) and Cu(U11)2Cl2 (IC50 = 33.4 ± 3.8 μM) demonstrate enhanced activity against the drug resistant NCI-H1975 cells with moderate selectivity toward normal WI-26 VA4 cells. The antiproliferative mechanism of cell death underlying the growth inhibitory effect of the synthesized complexes was studied via additional experiments, including the cell cycle analysis and the apoptosis induction test. Reassuringly, certain 2-pyridyl urea-based Cu(II) complexes exerted cell line-specific antiproliferative effect which renders them valuable starting points for further unveiling the anticancer potential of this class of coordination compounds.

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π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

Cited by 42 publications

References 93 publications

Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation

Thiazolidin-4-Ones as Potential Antimicrobial Agents: Experimental and In Silico Evaluation

“Urea to Urea” Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents

Synthesis, Structure, and Antiproliferative Action of 2-Pyridyl Urea-Based Cu(II) Complexes

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