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
Tóm tắt
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.
Tài liệu tham khảo
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
Pedersen, C.J.: The discovery of crown ethers. Science 241, 536–540 (1988). https://doi.org/10.1126/science.241.4865.536
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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)
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
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
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
Klapötke, T.M.: Chemistry of high-energy materials, 3rd edn. De Gruyter, Berlin (2015)
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
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