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Synthesis, structural aspects, antimicrobial activity and ion transport investigation of five new [1+1] condensed cycloheterophane peptides

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Abstract

Five novel [1+1] condensed cycloheterophane peptides were synthesized via reaction of pyridine-2,6-bis(2-aminothiophenoxymethyl) with several diacid chlorides: glutaryl dichloride, adipoyl dichloride, 2,2′-thiodiacetyl chloride, dithiodiglycoloyl chloride and 3,3′-thiodipropionoyl chloride combinations (L 1 –L 5 ). The compounds were characterized by elemental analyses, mass, FT-IR, 1H, and 13C NMR spectral data. The antimicrobial activities of the compounds were evaluated using the disk diffusion method in dimethyl sulfoxide as well as the minimal inhibitory concentration dilution method, against several bacteria and yeast cultures. The results were compared with those of commercial antibiotic and antifungal agents. Structure activity relationships were also discussed. Permeability of compound L 5 against Na+ and K+ were also investigated.

Graphical abstract

Five novel cycoloheterophane amides were synthesized. Mass spectra reveal their [1+1] cyclic condensation. The compounds exert moderate microbial activity. Thia and aza groups seem to be a key element of microbial potency.

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Acknowledgments

We would like to extend our gratitude to the Fatih University Scientific Research Centre (Project-P50021004_G1452) and the Trakya University (Grant # TÜBAP-2010/174) for their financial support. Dr. Ahmet Ceyhan Gören and Gökhan Bilsel (TUBİTAK-UME), is acknowledged for the Mass analysis.

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Authors and Affiliations

  1. Department of Chemistry, Trakya University, Edirne, Turkey

    Ömer Zaim & Çağlar Baydar

  2. Department of Chemistry, Fatih University, Büyükçekmece, Istanbul, 34500, Turkey

    Naz Mohammed Aghatabay & Mustafa Ulvi Gürbüz

  3. Department of Biology, Duzce University, Duzce, Turkey

    Başaran Dülger

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  1. Ömer Zaim
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  2. Naz Mohammed Aghatabay
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  3. Mustafa Ulvi Gürbüz
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  4. Çağlar Baydar
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  5. Başaran Dülger
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Correspondence to Ömer Zaim.

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Zaim, Ö., Aghatabay, N.M., Gürbüz, M.U. et al. Synthesis, structural aspects, antimicrobial activity and ion transport investigation of five new [1+1] condensed cycloheterophane peptides. J Incl Phenom Macrocycl Chem 78, 151–159 (2014). https://doi.org/10.1007/s10847-012-0282-x

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  • DOI: https://doi.org/10.1007/s10847-012-0282-x

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