Synthesis, Structural Aspects, Antimicrobial Activity, and Ion Transport Investigations of Four New [1+1] Condensed 12-Membered Cyclophane Amides

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dc.authoridKARABULUT, H R Ferhat/0000-0002-9501-6296
dc.authoridGurbuz, Mustafa Ulvi/0000-0002-8684-5746
dc.authorwosidKARABULUT, H R Ferhat/AAA-1402-2021
dc.contributor.authorGurbuez, Mustafa Ulvi
dc.contributor.authorAghatabay, Naz Mohammed
dc.contributor.authorKarabulut, H. Riza Ferhat
dc.date.accessioned2024-06-12T11:19:34Z
dc.date.available2024-06-12T11:19:34Z
dc.date.issued2017
dc.departmentTrakya Üniversitesien_US
dc.description.abstractTwo new diamines (a, b) and their four [1+1] condensed macrocyclic peptides (c-f) were synthesized via dilution method affording the expected dilactams in reasonably high-yield yields. The compounds were characterized by elemental analyses, mass, FT-IR, H-1, and C-13 NMR spectral data. Mass spectra reveal their [1+1] cyclic condensation. The macrocycles having two peptide units in the ring would constitute three configurational isomers: cisoid-cisoid, transoid-transoid, and cisoid-transoid. Their H-1 and C-13 NMR show one signal for each chemically equivalent SCH2 and CONH and could be assigned symmetrical structures lacking any configurational isomerism. The ion transport activity of the compounds (c) and (d) on Na+ and K+ ions were evaluated by CH2Cl2 liquid-liquid membrane method using a U tube system. Slightly higher affinity for potassium than sodium was also observed, which is undoubtedly related to the matching size of the cavity between K+ and cyclic peptides. The antimicrobial and antifungal activities of four macrocyclic amides (c, d, e, and f) were illuminated using disk diffusion method in dimethyl sulfoxide as well as the minimal inhibitory concentration dilution method, against several bacteria and yeast cultures. Comparing all methods, in most cases, the (e) and (f) compound seems to show slightly higher biological activity than the (c) and (d) macrocycles. This may be because of the presence of extra chlorine atoms on the exterior part of the molecules.en_US
dc.description.sponsorshipFatih University Scientific Research Centre [P50021004_G1452]en_US
dc.description.sponsorshipWe would like to extend our gratitude to the Fatih University Scientific Research Centre for their financial support under project-P50021004_G1452.en_US
dc.identifier.doi10.1002/jhet.2659
dc.identifier.endpage958en_US
dc.identifier.issn0022-152X
dc.identifier.issn1943-5193
dc.identifier.issue2en_US
dc.identifier.scopus2-s2.0-84969930009en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage952en_US
dc.identifier.urihttps://doi.org/10.1002/jhet.2659
dc.identifier.urihttps://hdl.handle.net/20.500.14551/25263
dc.identifier.volume54en_US
dc.identifier.wosWOS:000397563000016en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofJournal Of Heterocyclic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectPhane Nomenclatureen_US
dc.subjectCyclic-Peptidesen_US
dc.subjectDesignen_US
dc.subjectDepsipeptidesen_US
dc.titleSynthesis, Structural Aspects, Antimicrobial Activity, and Ion Transport Investigations of Four New [1+1] Condensed 12-Membered Cyclophane Amidesen_US
dc.typeArticleen_US

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