Efficient syntheses and antimicrobial activities of new thiophene containing pyranone and quinolinone derivatives using manganese(<scp>iii</scp>) acetate: the effect of thiophene on ring closure–opening reactions

Özgür, Mehtap; Yılmaz, Mehmet; Nishino, Hiroshi; Avar, Eda Çinar; Dal, Hakan; Pekel, A. Tarık; Hökelek, Tuncer

doi:10.1039/c9nj00054b

Cited by 23 publications

(8 citation statements)

References 73 publications

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“…A study on a series of manganese(I) tricarbonyl complexes bearing bis(2-pyridinylmethyl)(2-quinolinylmethyl)amine, bis(2-quinolinylmethyl)(2-pyridinylmethyl)amine, tris(2-quinolinylmethyl)amine, and tris(2-pyridinylmethyl)amine ligands (17, Figure 3), was reported recently by Güntzel and coworkers [58] [59]. Several other manganese metal complexes have been recently tested for their antimicrobial efficacy but were not found to be active [60][61][62][63].…”

Section: Manganese Complexesmentioning

confidence: 87%

Recent Studies on the Antimicrobial Activity of Transition Metal Complexes of Groups 6–12

Sovari

Zobi

2020

Chemistry

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Antimicrobial resistance is an increasingly serious threat to global public health that requires innovative solutions to counteract new resistance mechanisms emerging and spreading globally in infectious pathogens. Classic organic antibiotics are rapidly exhausting the structural variations available for an effective antimicrobial drug and new compounds emerging from the industrial pharmaceutical pipeline will likely have a short-term and limited impact before the pathogens can adapt. Inorganic and organometallic complexes offer the opportunity to discover and develop new active antimicrobial agents by exploiting their wide range of three-dimensional geometries and virtually infinite design possibilities that can affect their substitution kinetics, charge, lipophilicity, biological targets and modes of action. This review describes recent studies on the antimicrobial activity of transition metal complexes of groups 6–12. It focuses on the effectiveness of the metal complexes in relation to the rich structural chemical variations of the same. The aim is to provide a short vade mecum for the readers interested in the subject that can complement other reviews.

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Section: Manganese Complexesmentioning

confidence: 87%

Recent Studies on the Antimicrobial Activity of Transition Metal Complexes of Groups 6–12

Sovari

Zobi

2020

Chemistry

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“…A synthetic approach based on Mn(III) oxidative radical cyclization of cyclic 1,3‐diketones with 1,1‐disubstituted alkenes afforded a large library of thiophene‐substituted dihydrofuran‐fused pyranones, coumarins and quinolinones, out of which only a small number of compounds have been evaluated as antibacterial agents. [ 18 ] Dihydrofuran‐fused quinolinones presented a weak to moderate antibacterial activity, with compound 3 being the most potent against B. subtilis (MIC = 125 μg/ml) and Bacillus licheniformis (MIC = 500 μg/ml).…”

Section: Antimicrobial Compounds Based On Thiophene‐substituted Heter...mentioning

confidence: 99%

Thiophene‐containing compounds with antimicrobial activity

Roman¹

2022

Archiv der Pharmazie

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Thiophene, as a member of the group of five-membered heterocycles containing one heteroatom, is one of the simplest heterocyclic systems. Many synthetic strategies allow the accurate positioning of various functionalities onto the thiophene ring. This review provides a comprehensive, systematic and detailed account of the developments in the field of antimicrobial compounds featuring at least one thiophene ring in their structure, over the last decade.

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“…Manganese(III) acetate [33][34][35][36][37] and Cerium(IV) ammonium nitrate [38][39][40] are the most widely used transition metal salts in this reaction. Our research group has reported the synthesis of dihydrofuran compounds by the radical cyclization of 1,3-dicarbonyl compounds with various unsaturated systems such as aromatic conjugated alkenes [41,42], dienes [43,44] and conjugated amide derivatives [45,46] mediated by Manganese(III) acetate and Cerium(IV) ammonium nitrate.…”

Section: Introductionmentioning

confidence: 99%

Acetylcholinesterase inhibition, molecular docking and ADME prediction studies of new dihydrofuran-piperazine hybrid compounds

Sarı

Yılmaz

2021

Med Chem Res

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Novel acrylamide and methacryloyl carrying piperazine-dihydrofuran derivatives (3a-p) were designed and obtained from radical cyclizations of unsaturated piperazine derivatives (1a-f) with 1,3-dicarbonyl compounds (2a-c) mediated by Mn(OAc)3. Structures of obtained compounds were confirmed with 1 H NMR (proton nuclear magnetic resonance), 13 C NMR (Carbon-13 nuclear magnetic resonance), HRMS (High resolution mass spectrometry), FTIR (Fourier-transform infrared spectroscopy and melting point analysis. Inhibitory activites of all piperazine-dihydrofuran compounds were evaluated against AChE (Acetylcholinesterase) by Ellman method and test results showed that 3a, 3c, 3j and 3l are most active AChEI's (AChE inhibitors) of our work with IC50 (half-maximal inhibitory concentration) values of 2.62, 5.29, 1.17 and 3.90 µM, respectively. Furthermore, ligand-protein interactions and inhibitory activity mechanisms of 3a and 3j were investigated by molecular docking. Finally, in silico molecular property and ADME (absorption, distribution, metabolism and excretion) of potential AChEI's (AChE inhibitor) were predicted by PreADMET and Molinspiration webservers. It can be concluded that the lead compound 3j show excellent inhibiton and satisfactory druglike characteristics.

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Efficient syntheses and antimicrobial activities of new thiophene containing pyranone and quinolinone derivatives using manganese(iii) acetate: the effect of thiophene on ring closure–opening reactions

Abstract: The syntheses, spectroscopic properties, and antimicrobial activities of new pyranones and quinoline-based dihydrofurans accompanied by 3-alkenyl-substituted structures were investigated.

Cited by 23 publications

References 73 publications

Recent Studies on the Antimicrobial Activity of Transition Metal Complexes of Groups 6–12

Recent Studies on the Antimicrobial Activity of Transition Metal Complexes of Groups 6–12

Thiophene‐containing compounds with antimicrobial activity

Acetylcholinesterase inhibition, molecular docking and ADME prediction studies of new dihydrofuran-piperazine hybrid compounds

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