Synthesis, Characterization and Antifungal Evaluation of Novel Pyridazin-3(2<i>H</i>)-One Derivatives

Hamed, Mai Y.; Aly, Aly Fahmy; Abdullah, Nashwa Hamed; Ismail, Mahmoud F.

doi:10.1080/10406638.2022.2044865

Cited by 6 publications

(4 citation statements)

References 55 publications

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“…Free energy is broken down into constituent energy contributors that result from different interactions, providing remarkable accuracy at a computationally affordable price. THE BFE between protein and ligand complexes was calculated using AMBER22's Molecular Mechanics/Generalized Born Surface Area (MM/GBSA) method 14 , 17 , 18 . The BFE was computed using the latest 2750 frames (25 ns) of the roduction trajectry for each complex.…”

Section: Methodsmentioning

confidence: 99%

“…Lately thiosemicarbazones with general formula R 1 R 2 C= N –NH(C=S)NHR 12 and typical synthetic route involving condensation of thiosemicarbazide with aldehyde/ketone have been gaining popularity among medicinal chemists 13 . These scaffolds bear a range of biological activities like antibacterial 14 – 16 , antifungal 17 , 18 , antihelmintic 19 , 20 , antimalarial 21 , 22 , antiviral 23 , 24 , anticancer 25 , 26 , and antidiabetic potential 27 , 28 . Additionally, several research groups have documented the comprehensive account of the antidiabetic potential of thiosemicarbazones and coumarin based compounds Fig.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of novel coumarin-based thiosemicarbazones and their implications in diabetic management via in-vitro and in-silico approaches

Zahra,

Ullah,

Halim

et al. 2023

Sci Rep

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Diabetes mellitus has a high prevalence rate and it has been deemed a severe chronic metabolic disorder with long-term complications. This research aimed to identify compounds that could potentially inhibit the vital metabolic enzyme α-glucosidase and thereby exert an anti-hyperglycemic effect. The main goal was to establish an effective approach to control diabetes. To proceed with this study, a series of novel coumarin-derived thiosemicarbazones 3a–3m was synthesized and examined using a variety of spectroscopic methods. Moreover, all the compounds were subjected to α-glucosidase inhibition bioassay to evaluate their antidiabetic potential. Fortunately, all the compounds exhibited several folds potent α-glucosidase inhibitory activities with IC50 values ranging from 2.33 to 22.11 µM, in comparison to the standard drug acarbose (IC50 = 873.34 ± 1.67 µM). The kinetic studies of compound 3c displayed concentration-dependent inhibition. Furthermore, the binding modes of these molecules were elucidated through a molecular docking strategy which depicted that the thiosemicarbazide moiety of these molecules plays a significant role in the interaction with different residues of the α-glucosidase enzyme. However, their conformational difference is responsible for their varied inhibitory potential. The molecular dynamics simulations suggested that the top-ranked compounds (3c, 3g and 3i) have a substantial effect on the protein dynamics which alter the protein function and have stable attachment in the protein active pocket. The findings suggest that these molecules have the potential to be investigated further as novel antidiabetic medications.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of novel coumarin-based thiosemicarbazones and their implications in diabetic management via in-vitro and in-silico approaches

Zahra,

Ullah,

Halim

et al. 2023

Sci Rep

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“…One further route affording the pyrazole core formation involves [3+2] cycloaddition reactions of diazocompounds, nitrilimines with alkenes or alkynes [51][52][53][54][55]. For the synthesis of pyridazine ring systems, condensation reactions of 1,4-bifunctional reagents (4-oxocarboxylic acids or furan-2(5H)-ones [56][57][58][59], cyclic anhydrides [60,61]) with hydrazines commonly used as well as the Diels-Alder cycloaddition approach [62,63]. The ability of these heterocycles to act as effective agrochemicals also highlights their potential for the selective targeting of biological systems [36,37].…”

Section: Introductionmentioning

confidence: 99%

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Edilova,

Osipova,

Slepukhin

et al. 2023

IJMS

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A convenient approach to substituted pyrazoles and pyridazinones based on 1,2,4-triketones is presented. Chemo- and regiocontrol in condensations of t-Bu, Ph-, 2-thienyl-, and CO2Et-substituted 1,2,4-triketone analogs with hydrazines are described. The direction of preferential nucleophilic attack was shown to be switched depending on the substituent nature in triketone as well as the reaction conditions. The acid and temperature effects on the selectivity of condensations were revealed. Regiochemistry of heterocyclic core formation was confirmed by NMR and XRD studies. The facile construction of heterocyclic motifs bearing acetyl and (or) carbethoxy groups suggests them as promising mono- or bifunctional building blocks for subsequent transformations.

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“…Pyridazine and its polycyclic structures have still played an interesting role in organic chemistry because of their remarkable properties in forming supramolecular assembly [ 15 , 16 , 17 , 18 ]. Pyridazine molecules are important heterocycle scaffolds that reveal diverse biological activities in medicine [ 19 , 20 , 21 , 22 , 23 , 24 , 25 ] and agriculture [ 26 ]. For example, Pyridazomycin is an antifungal and antibiotic compound, the first pyridazine derivative isolated from a natural source [ 27 ].…”

Section: Introductionmentioning

confidence: 99%

Autoxidation of 4-Hydrazinylquinolin-2(1H)-one; Synthesis of Pyridazino[4,3-c:5,6-c′]diquinoline-6,7(5H,8H)-diones

et al. 2022

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An efficient synthesis of a series of pyridazino[4,3-c:5,6-c′]diquinolines was achieved via the autoxidation of 4-hydrazinylquinolin-2(1H)-ones. IR, NMR (1H and 13C), mass spectral data, and elemental analysis were used to fit and elucidate the structures of the newly synthesized compounds. X-ray structure analysis and theoretical calculations unequivocally proved the formation of the structure. The possible mechanism for the reaction is also discussed.

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Synthesis, Characterization and Antifungal Evaluation of Novel Pyridazin-3(2H)-One Derivatives

Cited by 6 publications

References 55 publications

Synthesis of novel coumarin-based thiosemicarbazones and their implications in diabetic management via in-vitro and in-silico approaches

Synthesis of novel coumarin-based thiosemicarbazones and their implications in diabetic management via in-vitro and in-silico approaches

Exploring Three Avenues: Chemo- and Regioselective Transformations of 1,2,4-Triketone Analogs into Pyrazoles and Pyridazinones

Autoxidation of 4-Hydrazinylquinolin-2(1H)-one; Synthesis of Pyridazino[4,3-c:5,6-c′]diquinoline-6,7(5H,8H)-diones

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