Synthesis and Molecular Docking Studies of (E)-4-(Substituted-benzylideneamino)-2H-Chromen-2-one Derivatives: Entry to New Carbonic Anhydrase Class Of Inhibitors

Fattah, Tanzeela Abdul; Saeed, Aamer; Channar, Pervaiz Ali; Larik, Fayaz Ali; Hassan, Mubashir; Raza, Hussain; Abbas, Qamar

doi:10.1055/s-0043-123998

Cited by 19 publications

(13 citation statements)

References 28 publications

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“…The other residues which are present around 3b are Ser1, His2, His3, Trp4, Gly5, His9, Asn10, Gly63, His63, Phe229, and Leu237. Recent literature data also favor our docking results (Fattah et al, ). The 3c ‐receptor docked complex revealed the good conformational state with good interaction pattern within the receptor binding pocket.…”

Section: Resultssupporting

confidence: 88%

“…The ligands-protein binding analyses showed that 3b is confined in the active binding pocket of target protein as mentioned in docking results (Fattah et al, 2018). The 3c-receptor docked complex revealed the good conformational state with good interaction pattern within the receptor binding pocket.…”

Section: Docking Energy and Binding Analysis Of Synthesized Compoundsmentioning

confidence: 75%

“…The structure was then minimized to reach the converged root mean square deviation (RMSD) of 0.30 Å with the OPLS_2005 force field. The active site of the enzyme is defined from the co‐crystallized ligands from PDB and literature data (Fattah et al, ). Furthermore, docking experiment was performed against all synthesized ligands and target protein by using glide docking protocol (Friesner et al, ).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, carbonic anhydrase inhibitory activity and antioxidant activity of some 1,3‐oxazine derivatives

Qamar

Saeed

et al. 2018

Drug Development Research

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Hit, Lead & Candidate Discovery A series of 1‐(6‐methyl‐2‐substituted phenyl‐4‐thioxo‐4H‐1,3‐oxazin‐5‐yl)ethanones (3a‐n) were synthesized by the reaction of benzoyl isothiocyanates with active methylene compound acetylacetone in the presence of triethyl amine in a one‐pot process. The structures of the products were elucidated by elemental analyses, FT‐IR, 1H NMR, 13C NMR, and mass spectroscopy. These new 1,3‐oxazine derivatives were evaluated for their inhibitory activity against carbonic anhydrase II. Results for in vitro assay revealed that compound 3b having 4‐methoxy phenyl moiety was the most potent inhibitor with IC50 value of 0.144 ± 0.008 μM. It exhibited higher enzyme inhibitory activity as compared to the standard acetazolamide (IC50 = 0.997 ± 0.061 μM). The compounds 3c, 3h, and 3n also displayed superior inhibitory activities compared to the rest of the synthesized oxazine derivatives. The radical scavenging activity of oxazine derivatives was also performed and it was found that compounds showed moderate antioxidant activity. Lipinski rule confirmed the therapeutic potential of the synthesized compounds. Molecular docking studies were also performed to further understand the binding affinity of these compounds with PDBID 1V9E which confirmed that the synthesized derivatives bind in the active binding site of the target protein. Based upon our results, it is proposed that compound 3b may serve as a lead structure to design more potent carbonic anhydrase inhibitors.

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Section: Resultssupporting

confidence: 88%

Section: Docking Energy and Binding Analysis Of Synthesized Compoundsmentioning

confidence: 75%

Section: Methodsmentioning

confidence: 99%

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Synthesis, carbonic anhydrase inhibitory activity and antioxidant activity of some 1,3‐oxazine derivatives

Qamar

Saeed

et al. 2018

Drug Development Research

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“…A large number of sulfonamide‐based carbonic anhydrase inhibitor (CAI) drugs like are in clinical use for more than 70 years as diuretics, antiglaucoma, anticonvulsant, or anti‐infective drugs examples of clinically used CAIs: acetazolamide AZM, methazolamide MZA, ethoxzolamide EZA, dorzolamide DZA, brinzolamide BRZ, zonisamide ZNS, sulpiride SLP, indisulam IND, celecoxib CLX (Figure ) …”

Section: Introductionmentioning

confidence: 99%

“…A large number of sulfonamide-based carbonic anhydrase inhibitor (CAI) drugs like are in clinical use for more Figure 2). [12][13][14] However, due to numerous isoform of carbonic anhydrase enzyme, the search to obtain effective safe drug candidates is still work in progress.…”

Section: Introductionmentioning

confidence: 99%

Extending the scope of amantadine drug by incorporation of phenolic azo Schiff bases as potent selective inhibitors of carbonic anhydrase II, drug‐likeness and binding analysis

et al. 2018

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A series of Amantadine-based azo Schiff base dyes 6a-6e have been synthesized and characterized by H NMR and C NMR and evaluated for their in vitro carbonic anhydrase II inhibition activity and antioxidant activity. All of the synthesized showed excellent carbonic inhibition. Compound 6b was found to be the most potent derivative in the series, and the IC of 6b was found to be 0.0849 ± 0.00245 μm (standard Acetazolamide IC = 0.9975 ± 0.049 μm). The binding interactions of the most active analogs were confirmed through molecular docking studies. Docking studies showed 6b is interacting by making two hydrogen bonds w at His93 and Ser1 residues, respectively. All compounds showed a good drug score and followed Lipinski's rule. In summary, our studies have shown that these amantadine-derived phenolic azo Schiff base derivatives are a new class of carbonic anhydrase II inhibitors.

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Nicotinic acid‐supported cobalt ferrite‐catalyzed one‐pot synthesis of substituted chromeno[3,4‐b]quinolines

Kaldareh

Mokhtary

Nikpassand

2020

Applied Organom Chemis

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One‐pot synthesis of substituted chromeno[3,4‐b]quinoline derivatives was developed by three‐component reaction of aldehydes, dimedone or 1,3‐cyclohexadione, and 4‐aminocoumarin in the presence of nicotinic acid‐supported cobalt ferrite [CoFe2O4@SiO2@Si(CH2)3Cl@NA] as a novel magnetic catalyst in chloroform at reflux conditions. Nicotinic acid‐supported cobalt ferrite was characterized via Fourier transform infrared spectroscopy, X‐ray diffraction, thermal gravimetric analysis, scanning electron microscopy, high‐resolution transmission electron microscopy, energy‐dispersive X‐ray spectroscopy, and vibrating sample magnetometry. Moreover, the catalyst could be easily recovered by magnetic separation and recycled up to five times without significant loss of its catalytic activity. The products formed in excellent yields over appropriate reaction times under environmentally friendly conditions. High efficiency and easy isolation of the catalyst from products by simple magnetic attraction are some of the considerable advantages of this procedure.

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Synthesis and Molecular Docking Studies of (E)-4-(Substituted-benzylideneamino)-2H-Chromen-2-one Derivatives: Entry to New Carbonic Anhydrase Class Of Inhibitors

Cited by 19 publications

References 28 publications

Synthesis, carbonic anhydrase inhibitory activity and antioxidant activity of some 1,3‐oxazine derivatives

Synthesis, carbonic anhydrase inhibitory activity and antioxidant activity of some 1,3‐oxazine derivatives

Extending the scope of amantadine drug by incorporation of phenolic azo Schiff bases as potent selective inhibitors of carbonic anhydrase II, drug‐likeness and binding analysis

Nicotinic acid‐supported cobalt ferrite‐catalyzed one‐pot synthesis of substituted chromeno[3,4‐b]quinolines

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