Design and synthesis of antimicrobial, anticoagulant, and anticholinesterase hybrid molecules from 4-methylumbelliferone

Zayane, Marwa; Rahmouni, Ameur; Daami‐Remadi, Mejda; Mansour, Mohamed Ben; Romdhane, Anis; Jannet, Hichem Ben

doi:10.3109/14756366.2016.1158171

Cited by 24 publications

(8 citation statements)

References 45 publications

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“…The coumarin–1,2,3‐triazole conjugates 4 (Fig. ) exhibited significant in vitro antibacterial activity , while further incorporation of a chalcone moiety (hybrids 5 ) showed potential activity . The SAR revealed that the activity was affected greatly by the substituents on the chalcone moiety, and the contribution order of substituents on the activity was 4‐OMe > 4‐F > 4‐Cl > 4‐NMe 2 > 4‐ i ‐Pr > 4‐Me > ‐H; the number of ‐OMe on the chalcone moiety also influenced the activity greatly as evidenced by 3,4,5‐triOMe > 2,4‐diOMe > 4‐OMe.…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

Coumarin–triazole Hybrids and Their Biological Activities

Fan

Xing

Liu

2018

Journal of Heterocyclic Chem

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Hybridization is emerged as a promising strategy in the discovery of new drugs, especially these with complimentary activities and multiple pharmacological targets that are the potential weapons to prevent the drug resistance. Currently, several hybrids are under different stages of clinical trial, and may be introduced into clinical practice to treat various diseases in the near future. Triazoles including 1,2,3‐triazole and 1,2,4‐triazole as well as coumarins occupy an important position in medicinal chemistry attribute to their various biological activities, and some of them have been used in clinical practice. Obviously, hybridization of these two pharmacophores may lead to novel candidates with broader spectrum, more effective, lower toxicity, and multiple mechanisms of action. This review aims to outline the biological activities of coumarin–triazole hybrids, and discuss their structure–activity relationship to pave the way for the further rational development of this kind of hybrids.

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Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

Coumarin–triazole Hybrids and Their Biological Activities

Fan

Xing

Liu

2018

Journal of Heterocyclic Chem

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“…Coumarin motifs containing triazole, isoxazoles, isoxazolines, and aziridines were synthesized by Zayane’s team using 1,3-DP cycloaddition reactions. Synthesis of isoxazolines via 1,3-DP cycloaddition of in situ-generated RCNO to allyloxycumarin is presented below— Scheme 112 [ 120 ].…”

Section: Syntheses Of Substituted 2-isoxazolines Via 13-dp Cycloaddit...mentioning

confidence: 99%

“… Syntheses of 3,5-disubstituted 2-isoxazolines equipped with the coumarin motif attached to the scaffold through CH 2 O linker [ 120 ]. Ar = Ph and XC 6 H 4 (X = MeO, O 2 N, Et, Cl); a = PhMe, Et 3 N; up to 58% yield.…”

Section: Figures and Schemesmentioning

confidence: 99%

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

et al. 2023

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The involvement of 1,3-dipolar cycloaddition (1,3-DP), double bond migration, metathesis, and nitrile oxide (including in situ-generated nitrile oxide) as dipoles, together with the C=C bond containing dipolarophiles, in the syntheses of 2-isoxazolines is presented. Methods for synthesizing isoxazolines (other than 1,3-DP cycloaddition) were also presented briefly. Various methods of nitrile oxide preparation, especially in situ-generated procedures, are presented. Special attention was paid to the application of various combinations of 1,3-DP cycloaddition with double bond migration (DBM) and with alkene metathesis (AM) in the syntheses of trisubstituted isoxazolines. Allyl compounds of the type QCH2CH=CH2 (Q = ArO, ArS, Ar, and others) play the role of dipolarophile precursors in the combinations of DPC mentioned, DBM and AM. Mechanistic aspects of cycloadditions, i.e., concerted or stepwise reaction mechanism and their regio- and stereoselectivity are also discussed from experimental and theoretical points of view. Side reactions accompanying cycloaddition, especially nitrile oxide dimerization, are considered. 2-Isoxazoline applications in organic synthesis and their biological activity, broad utility in medicine, agriculture, and other fields were also raised. Some remaining challenges in the field of 1,3-DP cycloaddition in the syntheses of isoxazolines are finally discussed.

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“…Morpholinylmethyl- and piperazinylmethyl (N-R 1 ,R 2 )-containing hybrids exhibited noticeable activity against various bacterial pathogens and were more potent than the hybrids incorporating a phthalimidomethyl moiety in the 4 position of the triazole ring. The 6,8-disubstituted coumarin-1,2,3-triazole conjugates B (Figure 1) exhibited significant in vitro antibacterial activity [8,9]. Investigation of the antimicrobial activity of this type of hybrid compounds led to the identification of several different structural frameworks.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

et al. 2019

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Synthesis of 1,2,3-triazole-substituted coumarins and also 1,2,3-triazolyl or 1,2,3-triazolylalk-1-inyl-linked coumarin-2,3-furocoumarin hybrids was performed by employing the cross-coupling and copper catalyzed azide-alkyne cycloaddition reaction approaches. The synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, Bacillius subtilis, Actinomyces viscosus and Escherichia coli bacterial strains. Coumarin-benzoic acid hybrids 4с, 42с and 3-((4-acetylamino-3-(methoxycarbonyl)phenyl)ethynyl)coumarin (29) showed promising activity against S. aureus strains, and the 1,2,3-triazolyloct-1-inyl linked coumarin-2,3-furocoumarin hybrid 37c was endowed with high selectivity against B. subtilis and E. coli species. The in vitro antibacterial activity of 4с, 29, 37c and 42с can potentially be compared with that of a number of modern antibiotic drugs used in the clinic, suggesting promising prospects for further research. A detailed study of the molecular interactions with the targeted protein MurB was performed using docking simulations and the obtained results are quite promising.

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Design and synthesis of antimicrobial, anticoagulant, and anticholinesterase hybrid molecules from 4-methylumbelliferone

Cited by 24 publications

References 45 publications

Coumarin–triazole Hybrids and Their Biological Activities

Coumarin–triazole Hybrids and Their Biological Activities

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-triazole Hybrids Obtained from Natural Furocoumarin Peucedanin

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