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Synthesis and Analysis of Antimicrobial Properties of Macrocyclic Compounds Containing Thiophene and Furan Rings

Yıl 2019, , 170 - 174, 01.04.2019
https://doi.org/10.19113/sdufenbed.470761

Öz










Macrocylic
compounds  are functional compounds which
have  different applications in many
fields of chemistry. In this work, new macrocyclic ethers containing furan and
thiophene rings were obtained in good yields using different methods.
In addition, antimicrobial activities of these
compounds against Escherichia coli
ATCC 25922, Salmonella thphimurium
ATCC 14028, Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 11778, and Listeria
monocytogenes
ATCC 19115 bacteria and antifungal activity on Candida albicans ATCC 10231 were
investigated.
It has
been found that the synthesized compounds show a moderate effect against some
bacterial species.
    

Kaynakça

  • [1] Fenton, R. R., Gauci, R., Junk, P.C., Lindoy, L. F., Luckay, R. C., Meehan, G. V., Price, J. R., Turner, P., ve Wei, G. 2002. Macrocyclic ligand design. Structure- function relationships involving the interaction of pyridinyl-containing, mixed oxygen-nitrogen donor macrocycles with cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II), silver(I) and lead(II). Journal of Chemical Society, 10 (2002), 2185-2193.
  • [2] Aghatabay, N. M., Mahmiani, Y., Cevik, H., Gucin, F., ve Dulger, B. 2008. Synthesis, FT-Raman, FT-IR, NMR spectroscopic characterization and antimicrobial activity of new mixed aza-oxo-thia macrocyclic compounds. Structural Chemistry, 19 (2008), 833-842.
  • [3] Hughes, R. A., Thompson, S. P., Alcaraz, L.,ve Moody, C. J. 2005. Total Synthesis of the Thiopeptide Antibiotic Amythiamicin D. Journal of American Chemical Society 127 (2005), 15644-15651.
  • [4] Napolitano, A., Rodriquez, M., Bruno, I., Marzocco, S., Autore, G., Riccioa, R., Gomez-Paloma, L.:2003. Synthesis, structural aspects and cytotoxicity of the natural cyclopeptides yunnanins A, C and phakellistatins 1. Tetrahedron, 59 (2003), 10203-10211.
  • [5] Rajakumar, P., Rasheed, A. M. A., Rabia, A. I., ve Chamundeeswari, D. 2006. Synthesis and study of anti-inflammatory activity of some novel cyclophane amides. Bioorganic and Medicinal Chemistry Letters, 16 (2006), 6019-6023.
  • [6] Bokesch, H.R., Pannell, L.K., Cochran, P.K., Sowder, R.C., McKee, T.C., Boyd, M.R. 2001. A novel anti-HIV macrocyclic peptide from Palicourea condensataI. Journal of Natural Products, 64 (2001), 249-250.
  • [7] Armstrong, L. G ve Lindoy. L. F. 1975. Nitrogen-oxygen donor macrocyclic ligands. I. Nickel(II) complexes of a new series of cyclic ligands derived from salicylaldehydes. Inorganic Chemistry, 14 (1975), 1322-1326.
  • [8] Reed, J. J., Bradshaw, J. S., Husathy, P., Izatt, R. M. ve Dalley, N. K. 1998. Synthesis and Complexation Properties of Pyrimidine‐Derived Crown Ether Ligands. Journal of Heterocyclic Chemistry, 35 (1998), 1-8.
  • [9] Herrera, A. M., Kalayda, G. V., Disch, J. S., Wikstrom, J. P., Karendovych, I. V.,Staples, R. J., Campana, C. F., Nazarenko, A.Y., Haas, T. E. ve Rybak-Akimovz 2003. Reactions at the azomethine CN bonds in the nickel(II) and copper(II) complexes of pyridine- containing Schiff-base macrocyclic ligands. Dalton Trans, (2003), 4482-4492.
  • [10] Zaim, Ö., Aghatabay N. M, Gürbüz M.U., Baydar Ç., ve Dülger B. 2014. Synthesis, structural aspects, antimicrobial activity and ion transport investigation of five new [1+1] condensed cycloheterophane peptides. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 78, (2014), 151-159.
  • [11] Aghatabay N. M., Parali Ö., Zaim Ö., Baydar Ç., Dülger B. 2014. Synthesis, structural aspects, antimicrobial activity and ion transportation investigation of four new [2 + 2] condensed 24 membered cycloheterphane peptides. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 79, (2014), 415-424.
  • [12] Gourdet, B., Singh, K., Stuart, A. M., Vidal, J. A. 2010. Di(1H,1H,2H,2H-perfluorooctyl)-dibenzo 18-crown-6: A "light fluorous" recyclable phase transfer catalyst. Journal of Fluorine Chemistry, 131, (2010), 1133-1143.
  • [13] Li, Y., Yang, H., Zhao, Q., Song, W., Han, J., Bu, X. 2012. Ratiometric and Selective Fluorescent Sensor for Zn2+ as an "Off-On-Off" Switch and Logic Gate. Inorganic Chemistry, 51, (2012), 9642-9648.
  • [14] Zhang, C., Pu, J., Wu, H., Cheng, S., Zhang, R., Zhagn, A., Zhang, M. 2011. The synthesis and mesophases studies of a novel discotic compound containing two triphenylene cores linked by crown ether. Molecular Crystals and Liquid Crystals, 542, (2011), 99-105.
  • [15] Ihara, T., Sueda, S., Inenaga, A., Fukuda, R. ve Takagi, M. 1997. Synthetic DNA Ligands Conjugated with Metal Binding Moiety. Regulation of the Interaction with DNA by Metal Ions and the Ligand Effect on Metal Assisted DNA Cleaving. Supramolecular Chemistry, 8 (1997), 93-111.
  • [16] McPhee, M. M. ve Kerwin S. M. 2001. Synthesis, DNA cleavage, and cytotoxicity of a series of bis(propargylic) sulfone crown ethers. Bioorganic and Medicinal Chemistry, 9, (2001), 2809-2818.
  • [17] Boyer, A. and Lautens, M. 2011. Rhodium catalyzed domino enantioselective synthesis of bicyclo[2.2.2]lactones. Angewandte Chemie 5, (2011), 7346-7349.
  • [18] T. Bogaschenko, S. Basok, C. Kulygina, A. Lyapunov, N. Lukyanenko, 2002. A Practical Synthesis of Benzocrown Ethers under Phase-Transfer Catalysis Conditions. Synthesis, 15 (2002), 2266-2270.
  • [19] CLSI 2006 M7- A7, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically.
  • [20] Kimberly M. Bongera, Richard J.B.H.N. van den Berga, Laura H. Heitmanb, Ad P. IJzermanb, Julia Oosteromc, Cornelis M. Timmersd, Herman S. Overkleefta, Gijsbert A. van der Marela, 2007. Synthesis and evaluation of homo-bivalent GnRHR ligands. Bioorganic and Medicinal Chemistry, 15, (2007), 4841-4856.

Tiyofen ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri ve Antimikrobiyal Özelliklerinin İncelenmesi

Yıl 2019, , 170 - 174, 01.04.2019
https://doi.org/10.19113/sdufenbed.470761

Öz

Makrosiklik
bileşikler, kimyanın pek çok alanında farklı uygulamalara sahip işlevsel
bileşiklerdir. Bu çalışmada da furan ve tiyofen heterosiklik halkalarını içeren
yeni makrosiklik eterler farklı reaksiyon şartları denenerek, en verimli
şekilde sentezlenmiştir. Ayrıca sentezlenen bu bileşiklerin Escherichia coli ATCC 25922, Salmonella thphimurium ATCC 14028, Staphylococcus aureus ATCC 25923, Bacillus cereus ATCC 11778 ve Listeria monocytogenes ATCC 19115
bakterilerine karşı antimikrobiyal aktiviteleri, Candida albicans ATCC 10231 mayaları üzerinde antifungal
aktiviteleri incelenmiştir. Sentezlenen bileşiklerin bazı bakteri türlerine
karşı ılımlı etki gösterdiği bulunmuştur.

Kaynakça

  • [1] Fenton, R. R., Gauci, R., Junk, P.C., Lindoy, L. F., Luckay, R. C., Meehan, G. V., Price, J. R., Turner, P., ve Wei, G. 2002. Macrocyclic ligand design. Structure- function relationships involving the interaction of pyridinyl-containing, mixed oxygen-nitrogen donor macrocycles with cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II), silver(I) and lead(II). Journal of Chemical Society, 10 (2002), 2185-2193.
  • [2] Aghatabay, N. M., Mahmiani, Y., Cevik, H., Gucin, F., ve Dulger, B. 2008. Synthesis, FT-Raman, FT-IR, NMR spectroscopic characterization and antimicrobial activity of new mixed aza-oxo-thia macrocyclic compounds. Structural Chemistry, 19 (2008), 833-842.
  • [3] Hughes, R. A., Thompson, S. P., Alcaraz, L.,ve Moody, C. J. 2005. Total Synthesis of the Thiopeptide Antibiotic Amythiamicin D. Journal of American Chemical Society 127 (2005), 15644-15651.
  • [4] Napolitano, A., Rodriquez, M., Bruno, I., Marzocco, S., Autore, G., Riccioa, R., Gomez-Paloma, L.:2003. Synthesis, structural aspects and cytotoxicity of the natural cyclopeptides yunnanins A, C and phakellistatins 1. Tetrahedron, 59 (2003), 10203-10211.
  • [5] Rajakumar, P., Rasheed, A. M. A., Rabia, A. I., ve Chamundeeswari, D. 2006. Synthesis and study of anti-inflammatory activity of some novel cyclophane amides. Bioorganic and Medicinal Chemistry Letters, 16 (2006), 6019-6023.
  • [6] Bokesch, H.R., Pannell, L.K., Cochran, P.K., Sowder, R.C., McKee, T.C., Boyd, M.R. 2001. A novel anti-HIV macrocyclic peptide from Palicourea condensataI. Journal of Natural Products, 64 (2001), 249-250.
  • [7] Armstrong, L. G ve Lindoy. L. F. 1975. Nitrogen-oxygen donor macrocyclic ligands. I. Nickel(II) complexes of a new series of cyclic ligands derived from salicylaldehydes. Inorganic Chemistry, 14 (1975), 1322-1326.
  • [8] Reed, J. J., Bradshaw, J. S., Husathy, P., Izatt, R. M. ve Dalley, N. K. 1998. Synthesis and Complexation Properties of Pyrimidine‐Derived Crown Ether Ligands. Journal of Heterocyclic Chemistry, 35 (1998), 1-8.
  • [9] Herrera, A. M., Kalayda, G. V., Disch, J. S., Wikstrom, J. P., Karendovych, I. V.,Staples, R. J., Campana, C. F., Nazarenko, A.Y., Haas, T. E. ve Rybak-Akimovz 2003. Reactions at the azomethine CN bonds in the nickel(II) and copper(II) complexes of pyridine- containing Schiff-base macrocyclic ligands. Dalton Trans, (2003), 4482-4492.
  • [10] Zaim, Ö., Aghatabay N. M, Gürbüz M.U., Baydar Ç., ve Dülger B. 2014. Synthesis, structural aspects, antimicrobial activity and ion transport investigation of five new [1+1] condensed cycloheterophane peptides. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 78, (2014), 151-159.
  • [11] Aghatabay N. M., Parali Ö., Zaim Ö., Baydar Ç., Dülger B. 2014. Synthesis, structural aspects, antimicrobial activity and ion transportation investigation of four new [2 + 2] condensed 24 membered cycloheterphane peptides. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 79, (2014), 415-424.
  • [12] Gourdet, B., Singh, K., Stuart, A. M., Vidal, J. A. 2010. Di(1H,1H,2H,2H-perfluorooctyl)-dibenzo 18-crown-6: A "light fluorous" recyclable phase transfer catalyst. Journal of Fluorine Chemistry, 131, (2010), 1133-1143.
  • [13] Li, Y., Yang, H., Zhao, Q., Song, W., Han, J., Bu, X. 2012. Ratiometric and Selective Fluorescent Sensor for Zn2+ as an "Off-On-Off" Switch and Logic Gate. Inorganic Chemistry, 51, (2012), 9642-9648.
  • [14] Zhang, C., Pu, J., Wu, H., Cheng, S., Zhang, R., Zhagn, A., Zhang, M. 2011. The synthesis and mesophases studies of a novel discotic compound containing two triphenylene cores linked by crown ether. Molecular Crystals and Liquid Crystals, 542, (2011), 99-105.
  • [15] Ihara, T., Sueda, S., Inenaga, A., Fukuda, R. ve Takagi, M. 1997. Synthetic DNA Ligands Conjugated with Metal Binding Moiety. Regulation of the Interaction with DNA by Metal Ions and the Ligand Effect on Metal Assisted DNA Cleaving. Supramolecular Chemistry, 8 (1997), 93-111.
  • [16] McPhee, M. M. ve Kerwin S. M. 2001. Synthesis, DNA cleavage, and cytotoxicity of a series of bis(propargylic) sulfone crown ethers. Bioorganic and Medicinal Chemistry, 9, (2001), 2809-2818.
  • [17] Boyer, A. and Lautens, M. 2011. Rhodium catalyzed domino enantioselective synthesis of bicyclo[2.2.2]lactones. Angewandte Chemie 5, (2011), 7346-7349.
  • [18] T. Bogaschenko, S. Basok, C. Kulygina, A. Lyapunov, N. Lukyanenko, 2002. A Practical Synthesis of Benzocrown Ethers under Phase-Transfer Catalysis Conditions. Synthesis, 15 (2002), 2266-2270.
  • [19] CLSI 2006 M7- A7, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically.
  • [20] Kimberly M. Bongera, Richard J.B.H.N. van den Berga, Laura H. Heitmanb, Ad P. IJzermanb, Julia Oosteromc, Cornelis M. Timmersd, Herman S. Overkleefta, Gijsbert A. van der Marela, 2007. Synthesis and evaluation of homo-bivalent GnRHR ligands. Bioorganic and Medicinal Chemistry, 15, (2007), 4841-4856.
Toplam 20 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Hafize Özcan 0000-0002-8031-6755

Yayımlanma Tarihi 1 Nisan 2019
Yayımlandığı Sayı Yıl 2019

Kaynak Göster

APA Özcan, H. (2019). Tiyofen ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri ve Antimikrobiyal Özelliklerinin İncelenmesi. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 23(1), 170-174. https://doi.org/10.19113/sdufenbed.470761
AMA Özcan H. Tiyofen ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri ve Antimikrobiyal Özelliklerinin İncelenmesi. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. Nisan 2019;23(1):170-174. doi:10.19113/sdufenbed.470761
Chicago Özcan, Hafize. “Tiyofen Ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri Ve Antimikrobiyal Özelliklerinin İncelenmesi”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23, sy. 1 (Nisan 2019): 170-74. https://doi.org/10.19113/sdufenbed.470761.
EndNote Özcan H (01 Nisan 2019) Tiyofen ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri ve Antimikrobiyal Özelliklerinin İncelenmesi. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23 1 170–174.
IEEE H. Özcan, “Tiyofen ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri ve Antimikrobiyal Özelliklerinin İncelenmesi”, Süleyman Demirel Üniv. Fen Bilim. Enst. Derg., c. 23, sy. 1, ss. 170–174, 2019, doi: 10.19113/sdufenbed.470761.
ISNAD Özcan, Hafize. “Tiyofen Ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri Ve Antimikrobiyal Özelliklerinin İncelenmesi”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 23/1 (Nisan 2019), 170-174. https://doi.org/10.19113/sdufenbed.470761.
JAMA Özcan H. Tiyofen ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri ve Antimikrobiyal Özelliklerinin İncelenmesi. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. 2019;23:170–174.
MLA Özcan, Hafize. “Tiyofen Ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri Ve Antimikrobiyal Özelliklerinin İncelenmesi”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 23, sy. 1, 2019, ss. 170-4, doi:10.19113/sdufenbed.470761.
Vancouver Özcan H. Tiyofen ve Furan Halkaları İçeren Makrosiklik Bileşiklerinin Sentezleri ve Antimikrobiyal Özelliklerinin İncelenmesi. Süleyman Demirel Üniv. Fen Bilim. Enst. Derg. 2019;23(1):170-4.

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