Novel diphenyl ether-heterocycles hybrids: Synthesis via Hantzsch and Biginelli reactions, molecular docking simulation, and antimicrobial activities

El-Gabry, Yassmen A.; Salem, Mostafa E.; Ibrahim, Nada S.; Elwahy, Ahmed H.M.; Abdelhamid, Ismail A.; Diab, Hadeer M.

doi:10.1016/j.molstruc.2023.136857

Cited by 6 publications

(3 citation statements)

References 71 publications

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“…There have been several reports of the antibacterial, anticancer, antiallergic, and other disease-fighting effects of bis-heterocycles. , Encouraged by the findings above and as part of our ongoing research interest in the synthesis of heterocycles and their bis-heterocyclic analogues, − we present the design and synthesis of novel hybrid molecules composed of diphenyl ether linked to various heterocyclic systems. In this context, we recently investigated the Hantzsch reaction for the manufacture of bis-dihydropyridine and their corresponding fused derivatives based on diphenyl ether, and their antibacterial activity against various bacterial strains was evaluated . (Figure ).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Novel Diphenyl Ether-Based Bis-Heterocycles as Novel Hybrid Molecules via Michael and Other Cyclocondensation Reactions

Salem,

El-Gabry,

Abdelhamid

et al. 2024

ACS Omega

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Molecular hybridization is a technique used in drug creation that involves combining the pharmacophoric moieties of multiple bioactive compounds to create a new hybrid molecule with better affinity and effectiveness. In this regard, we created unique hybrid molecules out of diphenyl ether-linked fused pyrans and other heterocycles. The Michael reaction of 4,4′-oxydibenzaldehyde with malononitrile and various active methylene derivatives, as well as enaminone derivatives, produced the matching bis-fused pyrans and fused pyridines, both connected to a diphenyl ether moiety. Furthermore, the acid-catalyzed reaction of 4,4′-oxydibenzaldehyde with dimedone or β-naphthol produced the corresponding new bis(hexahydro-1H-xanthene-1,8dione) and bis(14H-dibenzo[a,j]xanthene). The processes by which the target products are formed were also examined.

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Section: Introductionmentioning

confidence: 99%

“…In this context, we recently investigated the Hantzsch reaction for the manufacture of bis-dihydropyridine and their corresponding fused derivatives based on diphenyl ether, and their antibacterial activity against various bacterial strains was evaluated. 53 ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Diphenyl Ether-Based Bis-Heterocycles as Novel Hybrid Molecules via Michael and Other Cyclocondensation Reactions

Salem,

El-Gabry,

Abdelhamid

et al. 2024

ACS Omega

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“…The pharmacophore scaffolds of several compounds are combined to create hybrid molecules. In this regard, anticancer drugs that are safer and more effective than those presently on the market may benefit from hybridization. , In light of these findings, as well as our continuing interest in the synthesis of heterocycles − and their bis(heterocycles), − we sought to incorporate N -arylacetamide units into the backbone of thiazole to obtain a novel series of bis-thiazole derivatives linked through biologically active quinoxaline or thienothiophene cores using a “hybrid conjugation of bioactive ligands” approach. Our synthetic strategy employs 2-(4-(1-(2-carbamothioylhydrazineylidene)ethyl)phenoxy)- N -(aryl)acetamides, 2-(4-(2-bromoacetyl)phenoxy)- N -(aryl)acetamides, bis(4,1-phenylene)bis(2-bromoethan-1-ones) 7 , bis(α-bromoketone), and bis(thiosemicarbazone) as precursors (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Novel Scaffolds Based on Bis-thiazole Connected to Quinoxaline or Thienothiophene through 2-Phenoxy-N-arylacetamide Groups as New Hybrid Molecules: Synthesis, Antibacterial Activity, and Molecular Docking Investigations

Salem,

Abdullah,

Ibrahim

et al. 2023

ACS Omega

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The resistance of microorganisms to antimicrobials has endangered the health of many people across the world. Overcoming the resistance problem will require the invention of molecules with a new mechanism of action so that no crossresistance with existing therapies occurs. Because of their powerful antibacterial activity against a wide spectrum of Gram-positive and Gram-negative bacterial strains, heterocyclic compounds are appealing candidates for medicinal chemists. In this regard, as unique hybrid compounds, we synthesized a novel family of bisthiazoles linked to quinoxaline or thienothiophene via the 2-phenoxy-Narylacetamide moiety. The target compounds were synthesized by reacting the relevant bis(α-haloketones) with the corresponding thiosemicarbazones in EtOH at reflux with a few drops of TEA. Under comparable reaction conditions, the isomeric bis(thiazoles) were synthesized by reacting the appropriate bis(thiosemicarbazone) with the respective α-haloketones. The structures of the novel compounds were confirmed using elements and spectral data. All of the synthesized compounds were tested for antibacterial activity in vitro. With an inhibitory zone width of 12 mm, compound 12a had the same activity as the reference medication tobramycin against Staphylococcus aureus. Compound 12b showed 20 mg/mL as a minimum inhibitory concentration (MIC) against Bacillus subtilis. Some of the synthesized compounds were tested via molecular docking against two bacterial proteins (dihydrofolate reductase and tyrosyl-tRNA synthetase).

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Hantzsch‐like synthesis of isoquinolino[2,1‐a]quinoline‐12‐carbonitrile incorporating aryl or heteroaryl moieties at C‐13

Mohamed Teleb,

Hassaneen,

Abdelhamid

et al. 2023

Journal of Heterocyclic Chem

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The synthesis of a new series of the tetracyclic 13‐arylisoquinolino[2,1‐a]quinoline‐12‐carbonitrile has been accomplished using a straightforward and efficient method. The novel compounds were obtained via the Hantzsch‐like reaction of varieties of aldehydes with 2‐(isoquinolin‐1‐yl)acetonitrile and dimedone. The structures of the novel compounds were verified using elemental and spectroscopic data.

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Novel diphenyl ether-heterocycles hybrids: Synthesis via Hantzsch and Biginelli reactions, molecular docking simulation, and antimicrobial activities

Cited by 6 publications

References 71 publications

Synthesis of Novel Diphenyl Ether-Based Bis-Heterocycles as Novel Hybrid Molecules via Michael and Other Cyclocondensation Reactions

Synthesis of Novel Diphenyl Ether-Based Bis-Heterocycles as Novel Hybrid Molecules via Michael and Other Cyclocondensation Reactions

Novel Scaffolds Based on Bis-thiazole Connected to Quinoxaline or Thienothiophene through 2-Phenoxy-N-arylacetamide Groups as New Hybrid Molecules: Synthesis, Antibacterial Activity, and Molecular Docking Investigations

Hantzsch‐like synthesis of isoquinolino[2,1‐a]quinoline‐12‐carbonitrile incorporating aryl or heteroaryl moieties at C‐13

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