Expedient and click synthesis, spectroscopic characterizations and DFT calculations of novel 1,5-bis(N-substituted 1,2,3‒triazole) benzodiazepinedione scaffolds

Paghandeh, Hossein; Saeidian, Hamid

doi:10.1016/j.molstruc.2017.12.035

Cited by 16 publications

(6 citation statements)

References 23 publications

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“…In order to verify the bioactivity behavior in vitro of four compounds with broad-spectrum bioactivity, the frontier molecular orbitals (FMOs) are studied. The HOMO and LUMO represent the ability of donating electron and accepting the electron [34]. Both HOMO and LUMO are very important factors to understand the electronic transition and intermolecular interactions of molecular reactions, which provides insights for explicating biological activity [35][36][37].…”

Section: Homo-lumo Analysismentioning

confidence: 99%

Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking

Li¹,

Ren²,

Han³

et al. 2021

Rev. Chim.

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Seven 4-amino-5-substituted-1,2,4-triazole-3-thione Schiff base compounds were synthesized reacting 4-amino-5-substituted-1,2,4-triazole-3-thione with dichloro-substituted 5-pyrimidines, and the structures were verified by elemental analysis and spectroscopic techniques (FT-IR, 1H NMR). Additionally, in vitro antifungal activities of the compounds (named F1~F2; A1~A5) against Grape anthracnose and Wheat gibberellic have been evaluated. The compounds of F1, A4 and A5 were found to be potentially effective antifungal agents against Grape anthracnose, while the others showed the low bioactivity. The antifungal activity of all compounds against Wheat gibberellic were superior to that of fluconazole (standard drug, SD). Particularly, compounds of F1, A1, A4 and A5 exhibited a broad-spectrum antifungal activity against two fungus as compared to the others. Therefore, molecular docking study was carried out to explore the potential interaction between ligands and Fusarium graminearum (PDB ID: 5E9H). The results showed that four compounds had higher affinity compared with fluconazole and form the stable complex with the receptor. Besides, the frontier molecular orbitals (FMOs) and molecular electrostatic potentials (MEP) of four compounds with broad-spectrum antimicrobial activity were also calculated with DFT/ B3LYP /6-31G (d, p) method. The energy gap values (△ELUMO-HOMO) of all the synthesized compounds ranged from 3.307-3.375 eV, which was lower than that of SD (6.248 eV). Additionally, according to MEP the electrophile reaction of 5-substituted groups was beneficial to improving the biological activity against Wheat gibberellic and Grape anthracnose.

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Section: Homo-lumo Analysismentioning

confidence: 99%

Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking

Li¹,

Ren²,

Han³

et al. 2021

Rev. Chim.

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“…Due to the importance and application of 1,2,3-triazoles bearing the benzothiazole group [ 27 , 28 ], the synthesis of these derivatives is essential for organic chemists and biologists, and efforts are underway to design drugs based on these compounds with high activity and lower toxicity. As a result of our group’s experience synthesizing 1,4-disubstituted 1,2,3-triazole derivatives [ 29 , 30 , 31 , 32 , 33 , 34 ], the new 1,2,3-triazoles were prepared using benzothiazole groups 5a – f via a 1,3-dipolar cycloaddition of S -propargylated mercaptobenzothiazole 3 , sodium azide, and α-halo ester/amide 4 in the presence of CuSO 4 /sodium ascorbate in a mixture of H 2 O/ t -BuOH ( Scheme 1 ). The density functional theory (DFT) calculations, with the B3LYP/6-31 + G(d, p ) method, were applied to investigate the physicochemical properties of the characterized structure of 5e , including structural, electronic, and spectral analysis.…”

Section: Introductionmentioning

confidence: 99%

Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies

et al. 2022

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A new series of 1,2,3-triazole derivatives 5a–f based on benzothiazole were synthesized by the 1,3-dipolar cycloaddition reaction of S-propargyl mercaptobenzothiazole and α-halo ester/amide in moderate to good yields (47–75%). The structure of all products was characterized by 1H NMR, 13C NMR, and CHN elemental data. This protocol is easy and green and proceeds under mild and green reaction conditions with available starting materials. The structural and electronic analysis and 1H and 13C chemical shifts of the characterized structure of 5e were also calculated by applying the B3LYP/6-31 + G(d, p) level of density functional theory (DFT) method. In the final section, all the synthesized compounds were evaluated for their anti-inflammatory activity by biochemical COX-2 inhibition, antifungal inhibition with CYP51, anti-tuberculosis target protein ENR, DPRE1, pks13, and Thymidylate kinase by molecular docking studies. The ADMET analysis of the molecules 5a–f revealed that 5d and 5a are the most-promising drug-like molecules out of the six synthesized molecules.

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“…[8,9] In addition, 1,5-benzodiazepines have shown additional and interesting bioactivities when they contain 1,2,3-triazoles moieties. [10][11][12] Moreover, on the basis of previous studies, it has been highlighted that the linkage of the triazole nucleus to an aromatic sulfonamide and a heteroaromatic group at the same time could give rise to potent inhibitors against physiologically or pathologically relevant isoforms enzymes such as human carbonic anhydrases (hCAs). [13,14] These enzymes are zinc metalloenzymes that act efficiently as catalysts for the reversible hydration of carbon dioxide to bicarbonate (CO 2 + H 2 O ⇆ HCO 3 − + H + ).…”

Section: Introductionmentioning

confidence: 99%

1,5‐Benzodiazepines as a platform for the design of carbonic anhydrase inhibitors

Ismail

Nocentini

Winum

et al. 2021

Archiv der Pharmazie

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A series of novel N-triazolo-benzene sulfonamides-1,5-benzodiazepines 9a-d and 10dwere designed and prepared through the copper-catalyzed azide alkyne cycloaddition click chemistry procedure, reacting the N 1 -propargyl-1,5-benzodiazepine 2 and the N 1 ,N 5 -dipropargyl analog 6 with various benzene sulfonamide azides 8a-d. The synthesized compounds were found to show nanomolar affinity toward relevant isoforms of human carbonic anhydrase such as hCA I, II, IV, VII, IX, and XII. The divalent derivative 10d showed a particularly high inhibitory activity against all hCA isoforms when compared with acetazolamide, and showed potent multivalent effects, better than reported previously for divalent CA inhibitors.

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Expedient and click synthesis, spectroscopic characterizations and DFT calculations of novel 1,5-bis(N-substituted 1,2,3‒triazole) benzodiazepinedione scaffolds

Cited by 16 publications

References 23 publications

Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking

Novel Pyrimidine-Triazole Schiff Bases: Synthesis, Antifungal Activities, DFT and Molecular Docking

Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies

1,5‐Benzodiazepines as a platform for the design of carbonic anhydrase inhibitors

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