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Synthesis, antimicrobial and thermal studies of nitropyridine-substituted double armed benzo-15-crown-5 ligands; alkali (Na+ and K+) and transition metal (Ag+) complexes; reduction of nitro compounds

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Abstract

Nitropyridine substituted double-armed benzo 15-crown-5 compounds (1–4) were synthesized by the reactions of 4′,5′-bis(bromomethyl)benzo-15-crown-5 with hydroxypyridine derivatives. Na+ and K+ complexes (1a–4a, 1b–4b) of crown ether compounds (1–4) were prepared with sodium picrate and potassium picrate, respectively. Transition metal complexes (1c–4c) of the synthesized ligands (1–4) were prepared from Ag+ cation. In addition, nitro compounds (1, 2 and 4) were reduced by using Pd/C and hydrazine hydrate and new amine compounds (5, 6 and 8) were obtained. The structures of new double-armed crown ether compounds (2–4), their metal complexes (1a–4a, 1b–4b, 2c–4c) and amine compounds (5, 6 and 8) were elucidated by FTIR, HRMS, 1H–NMR, 13C–NMR spectroscopic methods. The thermal behaviors of these nitro group containing ligands (1–4) were compared with the resulting silver complexes (1c–4c) and amine compounds (5, 6 and 8). All synthesized compounds were examined for antibacterial activity against pathogenic strains Listeria monocytogenes, Salmonella typhi H, Bacillus cereus, Staphylococcus aureus, Staphylococcus epidermidis, Micrococcus luteus, Escherichia coli, Klebsiella pneumonia, Proteus vulgaris, Serratia marcescens, Shigella dysenteria and antifungal activity against Candida albicans.

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References

  1. Pedersen, C.J.: Cyclic polyethers and their complexes with metal salts. J. Am. Chem. Soc. 89, 7017–7036 (1967). https://doi.org/10.1021/ja01002a035

    Article  CAS  Google Scholar 

  2. Pedersen, C.J.: The discovery of crown ethers. Science 241, 536–540 (1988). https://doi.org/10.1126/science.241.4865.536

    Article  PubMed  CAS  Google Scholar 

  3. Gokel, G.W., Leevy, W.M., Weber, M.E.: Crown ethers: sensors for ions and molecular scaffolds for materials and biological models. Chem. Rev. 104, 2723–2750 (2004). https://doi.org/10.1021/cr020080k

    Article  PubMed  CAS  Google Scholar 

  4. Li, J., Yim, D., Jang, W.D., Yoon, J.: Recent progress in the design and applications of fluorescence probes containing crown ethers. Chem. Soc. Rev. 46, 2437–2458 (2017). https://doi.org/10.1039/C6CS00619A

    Article  PubMed  CAS  Google Scholar 

  5. Zhang, G., Zhang, D., Zhou, Y., Zhu, D.: A new tetrathiafulvalene-anthracence dyad fusion with the crown ether group: fluorescence modulation with Na+ and C60, mimicking the performance of an “AND” logic gate. J. Org. Chem. 71, 3970–3972 (2006). https://doi.org/10.1021/jo052494u

    Article  PubMed  CAS  Google Scholar 

  6. Gawley, R.E., Mao, H., Haque, M.M., Thorne, J.B., Pharr, J.S.: Visible fluorescence chemosensor for saxitoxin. J. Org. Chem. 72, 2187–2191 (2007). https://doi.org/10.1021/jo062506r

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  7. Pond, S.J.K., Tsutsumi, O., Rumi, M., Kwon, O., Zojer, E., Brédas, J.L., Marder, S.R., Perry, J.W.: Metal-ion sensing fluorophores with large two-photon absorption cross sections: Aza-crown ether substituted donor-acceptor-donor distyrylbenzenes. J. Am. Chem. Soc. 126, 9291–9306 (2004). https://doi.org/10.1021/ja049013t

    Article  PubMed  CAS  Google Scholar 

  8. Tso, W.W., Fung, W.P.: Correlation between the antibacterial activity and alkali metal ion transport efficiency of crown ether. Inorg. Chim. Acta 55, 129–134 (1981). https://doi.org/10.1016/S0020-1693(00)90794-1

    Article  CAS  Google Scholar 

  9. Marjanović, M., Kralj, M., Supak, F., Frkanec, L., Piantanida, I., Šmuc, T., Tušek-Božić, L.: Antitumor potential of crown ethers: structure-activity relationships, cell cycle disturbances, and cell death studies of a series of ionophores. J. Med. Chem. 50, 1007–1018 (2007). https://doi.org/10.1021/jm061162u

    Article  PubMed  CAS  Google Scholar 

  10. Altaf, M., Stoeckli-Evans, H., Cuin, A., Sato, D., Pavan, F., Leite, C., Ahmad, S., Bouakka, M., Mimouni, M., Khardli, F., Hadda, T.: Synthesis, crystal structures, antimicrobial, antifungal andantituberculosis activities of mixed ligand silver(I) complexes. Polyhedron 138, 138–147 (2013). https://doi.org/10.1016/j.poly.2013.06.021

    Article  CAS  Google Scholar 

  11. Koçoğlu, S., Hayvali, Z., Ogutcu, H.: A polydentate ligand based on 2,2’-dipyridylamine unit linked benzo-15-crown-5; alkali and transition metal complexes; photoresponsive ligand; antimicrobial evaluation against pathogenic microorganisms. Trans. Met. Chem. 46, 509–522 (2021). https://doi.org/10.1007/s11243-021-00469-1

    Article  CAS  Google Scholar 

  12. Hayvalı, Z., Guler, H., Ogutcu, H., Sarı, N.: Novel bis-crown ethers and their sodium complexes as antimicrobial agent: synthesis and spectroscopic characterizations. Med. Chem. Res. 23, 652–3661 (2014). https://doi.org/10.1007/s00044-014-0937-9

    Article  CAS  Google Scholar 

  13. Ackermann, L., Diers, E., Manvar, A.: Ruthenium-catalyzed C−H bond arylations of arenes bearing removable directing groups via six-Mmembered ruthenacycles. Org. Lett. 14, 1154–1157 (2012). https://doi.org/10.1021/ol3000876

    Article  PubMed  CAS  Google Scholar 

  14. Liang, Y.F., Li, X., Wang, X., Yan, Y., Feng, P., Jiao, N.: Aerobic oxidation of PdII to PdIV by active radical reactants: direct C−H nitration and acylation of arenes via oxygenation process with molecular oxygen. ACS Catal. 5, 1956–1963 (2015). https://doi.org/10.1021/cs502126n

    Article  CAS  Google Scholar 

  15. Lou, S.J., Chen, Q., Wang, Y.F., Xu, D.Q., Du, X.H., He, J.Q., Mao, Y.J., Xu, Z.Y.: Selective C-H bond fluorination of phenols with a removable directing group: late-stage fluorination of 2-phenoxyl nicotinate derivatives. ACS Catal. 5, 2846–2849 (2015). https://doi.org/10.1021/acscatal.5b00306

    Article  CAS  Google Scholar 

  16. Dai, W.C., Yang, B., Xu, S.H., Wang, Z.X.: Nickel-catalyzed cross-coupling of aryl 2-pyridyl ethers with organozinc reagents: removal of the directing group via cleavage of the carbon-oxygen bonds. J. Org. Chem. 86, 2235–2243 (2021). https://doi.org/10.1021/acs.joc.0c02389

    Article  PubMed  CAS  Google Scholar 

  17. Fleming, G.J.: Thermal analysis of nitro-substituted epoxide polymers. J. App. Polym. Sci. 13, 2579–2592 (1969). https://doi.org/10.1002/app.1969.070131206

    Article  CAS  Google Scholar 

  18. Yigiter, A.O., Atakol, M.K., Aksu, M.L., Atakol, O.: Thermal characterization and theoretical and experimental comparison of picryl chloride derivatives of heterocyclic energetic compounds. J. Therm. Anal. Calorim. 127, 2199–2213 (2017). https://doi.org/10.1007/s10973-016-5766-2

    Article  CAS  Google Scholar 

  19. Bernt, S., Guillerm, V., Serre, C., Stock, N.: Direct covalent post-synthetic chemical modification of Cr-MIL-101 using nitrating acid. Chem. Commun. 47, 2838–2840 (2011). https://doi.org/10.1039/C0CC04526H

    Article  CAS  Google Scholar 

  20. Atakol, A., Svoboda, I., Dal, H., Atakol, O., Nazır, H.: New energetic silver(I) complexes with Nnn type pyrazolylpyridine ligands and oxidizing anions. J. Mol. Struct. 1210, 128001 (2020). https://doi.org/10.1016/j.molstruc.2020.128001

    Article  CAS  Google Scholar 

  21. Bilgin, A., Ertem, B., Dinc Agın, P., Gok, Y., Karslıoglu, S.: Synthesis, characterization and extraction studies of a new vic-dioxime and its complexes containing bis(diazacrown ether) moieties. Polyhedron 25, 3165–3172 (2006). https://doi.org/10.1016/j.poly.2006.05.023

    Article  CAS  Google Scholar 

  22. Koçoğlu, S., Ogutcu, H., Hayvalı, Z.: Photophysical and antimicrobial properties of new double-armed benzo-15-crown-5 ligands and complexes. Res. Chem. Intermed. 45, 2403–2427 (2019). https://doi.org/10.1007/s11164-019-03741-3

    Article  CAS  Google Scholar 

  23. Calverley, M.J., Dale, J.: 1,4,7-Trioxa-10-azacyclododecane and some N-substituted derivatives; Synthesis and cation complexing. Acta Chem. Scand. B. 36, 241–247 (1982). https://doi.org/10.3891/acta.chem.scand.36b-0241

    Article  Google Scholar 

  24. Winkler, B., Mau, A.W.H., Dai, L.: Crown ether substituted phenylenevinylene oligomers: synthesis and electroluminescent properties. Phys. Chem. Chem. Phys. 2, 291–295 (2000). https://doi.org/10.1039/A907547J

    Article  CAS  Google Scholar 

  25. Sarı, N., Şahin, S.Ç., Öğütcü, H., Dede, Y., Yalçın, S., Altundas, A., Doğanay, K.: Ni(II)-tetrahedral complexes: characterization, antimicrobial properties, theoretical studies and a new family of charge-transfer transitions. Spectrochim. Acta A. 106, 60–67 (2013). https://doi.org/10.1016/j.saa.2012.12.078

    Article  CAS  Google Scholar 

  26. Rubab, S., Bahadur, S., Hanif, U., Durrani, A.I., Sadiqa, A., Shafique, S., Zafar, U., Shuaib, M., Urooj, Z., Nizamani, M.M., Iqbal, S.: Phytochemical and antimicrobial investigation of methanolic extract/ fraction of Ocimum basilicum L. Biocatal. Agric. Biotechnol. 31, 101894 (2021). https://doi.org/10.1016/j.bcab.2020.101894

    Article  CAS  Google Scholar 

  27. Nartop, D., Sarı, N., Altundaş, A., Öğütcü, H.: Synthesis, characterization, and antimicrobial properties of new polystyrene-bound Schiff bases and their some complexes. J. Appl. Polym. Sci. 125, 1796–1803 (2012). https://doi.org/10.1002/app.36270

    Article  CAS  Google Scholar 

  28. Çınarlı, M., Yüksektepe Ataol, Ç., Bati, H., Güntepe, F., Ögütçü, H., Büyükgüngör, O.: Synthesis, structural characterization, Hirshfeld analyses, and biological activity studies of Ni(II) and Zn(II) complexes containing the sulfonohydrazone group. Inorg. Chim. Acta 484, 87–94 (2019). https://doi.org/10.1016/j.ica.2018.09.027

    Article  CAS  Google Scholar 

  29. Barboiu, M., Meffre, A., Legrand, Y.M., Petit, E., Marin, L., Pinteala, M., Lee, A.V.D.: Frustrated ion-pair binding by heteroditopic macrocyclic receptors. Supramol. Chem. 26, 223–228 (2014). https://doi.org/10.1080/10610278.2013.852196

    Article  CAS  Google Scholar 

  30. Poonia, N.S., Bagdi, P., Sidhu, K.S.: Structural aspects of crown complexes with alkali and alkaline earth cations. Benzo-15-crown-5 as a discriminating macrocycle. J. Incl. Phenom. 4, 43–54 (1986). https://doi.org/10.1007/BF00662080

    Article  CAS  Google Scholar 

  31. Keller, B.O., Sui, J., Young, A.B., Whittal, R.M.: Interferences and contaminants encountered in modern mass spectrometry. Anal. Chim. Acta 627, 71–81 (2008). https://doi.org/10.1016/j.aca.2008.04.043

    Article  PubMed  CAS  Google Scholar 

  32. Tong, H., Bell, D., Tabei, K.: Siegel, MM: Automated data massaging, interpretation, and e-mailing modules for high throughput open access mass spectrometry. J. Am. Soc. Mass. Spectrom. 10, 1174–1187 (1999). https://doi.org/10.1016/S1044-0305(99)00090-2

    Article  CAS  Google Scholar 

  33. Ghildiyal, N., nee Pant, G.J., Rawat, M.S.M., Singh, K.: Spectral investigation of the effect of anion on the stability of non covalent assemblies of 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecine (benzo-15-crown-5) with sodium halides. Spectrochim. Acta A. 171, 507–514 (2017). https://doi.org/10.1016/j.saa.2016.07.044

    Article  CAS  Google Scholar 

  34. Liu, Y.: Han, JR, Zhang, HY: Assembly behavior and binding ability of double-armed benzo-15-crown-5 with the potassium ion. Supramol. Chem. 16, 247–254 (2004). https://doi.org/10.1080/10610270410001663796

    Article  CAS  Google Scholar 

  35. Şahin, D., Süzen, Y., Hayvalı, Z.: Double-armed benzo-15-crown-5 ligands and complexes and single crystal structure determination. Heteroatom Chem. 25, 43–54 (2014). https://doi.org/10.1002/hc.21134

    Article  CAS  Google Scholar 

  36. Şahin, D., Koçoğlu, S., Şener, O., Şenol, C., Dal, H., Hokelek, T., Hayvalı, Z.: New NO donor ligands and complexes containing furfuryl or crown ether moiety: Syntheses, crystal structures and tautomerism in ortho-hydroxy substituted compounds as studied by UV-vis spectrophotometry. J. Mol. Struct. 1102, 302–313 (2015). https://doi.org/10.1016/j.molstruc.2015.09.004

    Article  CAS  Google Scholar 

  37. Öğütçü, H., Kurnaz Yetim, N., Hasanoglu Özkan, E., Eren, O., Kaya, G., Sarı, N., Dişli, A.: Nanospheres caped Pt(II) and Pt (IV): synthesis and evaluation as antimicrobial and antifungal agent. P. J. Chem. Techn. 19, 74–80 (2017). https://doi.org/10.1515/pjct-2017-0011

    Article  CAS  Google Scholar 

  38. Çiçek, İ, Tunç, T., Ogutcu, H., Abdurrahmanoglu, S., Günel, A., Demirel, N.: Synthesis of novel chiral aminoalcohol and benzimidazole hybrids and investigation of their antimicrobial activities. Bioorg. Chem. 5, 4650–4654 (2020). https://doi.org/10.1002/slct.202000355

    Article  CAS  Google Scholar 

  39. Gul, D.S., Ogutcu, H., Hayvalı, Z.: Investigation of photophysical behavior and antimicrobial activity of novel benzo-15-crown-5 substituted coumarin and chromone derivatives. J. Mol. Struct. 1204, 127569 (2020). https://doi.org/10.1016/j.molstruc.2019.127569

    Article  CAS  Google Scholar 

  40. Nartop, D., Hasanoğlu Özkan, E., Gündem, M., Çeker, S., Ağar, G., Öğütcü, H., Sarı, N.: Synthesis, antimicrobial and antimutagenic effects of novel polymeric-Schiff bases including indol. J. Mol. Struct. 1195, 877–882 (2019). https://doi.org/10.1016/j.molstruc.2019.06.042

    Article  CAS  Google Scholar 

  41. Altundas, A., Erdogan, Y., Ögütcü, H., Kizil, H.E., Agar, G.: Synthesis and in-vitro antimicrobial and anti-mutagenic activities of some novel 2-(2-hydroxybenzylideneamino)-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carbonitrile derivatives. Fresen. Environ. Bull. 25, 5411–5418 (2016)

    CAS  Google Scholar 

  42. Nartop, D., Demirel, B., Güleç, M., Hasanoğlu Özkan, E., Kurnaz Yetim, N., Sarı, N., Çeker, S., Öğütcü, H., Ağar, G.: Synthesis, enzyme immobilization, antimutagenic activity and antimicrobial evulation against pathogenic microorganisms. J. Biochem. Mol. Tox. 34, e22432 (2020). https://doi.org/10.1002/jbt.22432

    Article  CAS  Google Scholar 

  43. Afzal, J., Ullah, N., Hussain, Z., Rukh, S., Ayaz, M., Akbar, A., Zaman, A.: Phytochemical an analysis and antibacterial potential of leaf extract of Bauhinia Linn.: An ethnomedicinal plant. Matrix Science Pharma 1, 17–19 (2017). https://doi.org/10.26480/msp.02.2017.17.19

    Article  Google Scholar 

  44. Atakol, O., Fuess, H., Kurtaran, R., Akay, A., Arici, C., Ergun, Ü.: Emregül, KC: Three new dinuclear silver(I) complexes derived from pyrazolyl type ligands. J. Therm. Anal. Calorim. 90, 517–523 (2007). https://doi.org/10.1007/s10973-006-7689-9

    Article  CAS  Google Scholar 

  45. Klapötke, T.M.: Chemistry of high-energy materials, 3rd edn. De Gruyter, Berlin (2015)

    Book  Google Scholar 

  46. Lizarraga, E., Zabaleta, C.: Palop, JA: thermal stability and decomposition of pharmaceutical compounds. J. Therm. Anal. Calorim. 89, 783–792 (2007). https://doi.org/10.1007/s10973-006-7746-4

    Article  CAS  Google Scholar 

  47. Apreutesei, D., Lisa, G., Hurduc, N., Scutaru, D.: Thermal behavior of some cholesteric esters. J. Therm. Anal. Calorim. 83, 335–340 (2006). https://doi.org/10.1007/s10973-005-6522-1

    Article  CAS  Google Scholar 

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Acknowledgements

The authors gratefully acknowledge the financial assistance of the Scientific and Technical Research Council of Turkey (TUBITAK), Grant No: TBAG 210T122, and Ankara University Grant No: 17B0430004.

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Authors and Affiliations

  1. Food Processing Department, Kahramankazan Vocational School, Başkent University, 06980, Ankara, Turkey

    Serhat Koçoğlu

  2. Department of Chemistry, Faculty of Science, Ankara University, 06100, Ankara, Turkey

    Serhat Koçoğlu, Zeliha Hayvalı & Orhan Atakol

  3. Department of Field Crops, Faculty of Agriculture, Kırşehir Ahi Evran University, 40100, Kırşehir, Turkey

    Hatice Ogutcu

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Koçoğlu, S., Hayvalı, Z., Ogutcu, H. et al. Synthesis, antimicrobial and thermal studies of nitropyridine-substituted double armed benzo-15-crown-5 ligands; alkali (Na+ and K+) and transition metal (Ag+) complexes; reduction of nitro compounds. J Incl Phenom Macrocycl Chem 102, 763–780 (2022). https://doi.org/10.1007/s10847-022-01157-y

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