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Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi ve Karakterizasyonu

Year 2020, , 1020 - 1032, 31.01.2020

Enes Hakkı Uluçay , Ersin Orhan

https://doi.org/10.29130/dubited.656633

Abstract

Bu çalışmada [(η6-p-simen)Ru(L2)Cl]CI genel formülüne sahip olan biyoaktif benzimidazol aren rutenyum organometalik bileşiği, salisilaldehitin 2-(aminometil)benzimidazol dihidroklorür(ambm2.2HCI) bileşiği ile reaksiyona sokulmasının ardından, [Ru(p-simen)klorür]2 eklenmesi ile hazırlandı. Biyoaktif benzimidazol aren rutenyum organometalik bileşiği UV-VIS, IR, ESI-MS, 1H NMR, 13C NMR spektroskopisi teknikleriyle karakterize edildi. Bileşiğin, Diferansiyel termal analiz (DTA) ve Termogravimetrik analiz (TGA) teknikleri ile ölçümleri yapıldı, ölçüm verileri incelendi.

Keywords

Aren rutenyum Benzimidazol Organometalik kimya Termal bozunma Biyoaktif Sentez

Supporting Institution

Düzce Üniversitesi

Project Number

2017.05.03.620

Thanks

Bu çalışma Düzce Üniversitesi Bilimsel Araştırma Projeleri tarafından desteklenmiştir (Proje no: 2017.05.03.620).

References

  • [1] M. J. Hannon, “Metal-based anticancer drugs: From a past anchored in platinum chemistry to a post-genomic future of diverse chemistry and biology,” Pure and Applied Chemistry, vol. 79, no. 12, pp. 2243–2261, 2007.
  • [2] S. Ghosh, “Cisplatin: The first metal based anticancer drug,” Bioorganic Chemistry, vol. 88, no. 1295, pp.1-20, 2019.
  • [3] A. A. Nazarov, C. G. Hartinger and P. J. Dyson, “Opening the lid on piano-stool complexes: An account of ruthenium(II)-arene complexes with medicinal applications,” Journal of Organometallic Chemistry, vol. 751, pp. 251-260, 2014.
  • [4] L. A. Malley, “Cisplatin,” in Encyclopedia of Toxicology, 3rd ed., vol. 1, National Library of Medicine, Bethesda, USA, 2005, pp. 614-616.
  • [5] E. Orhan, A. Garci and B. Therrien, “Coordination-driven self-assembly of arene ruthenium metalla-rectangles,” Inorganica Chimica Acta, vol. 461, pp. 78–83, 2017.
  • [6] E. Orhan, A. Garci, T. Riedel, P. J. Dyson and B. Therrien, “Cytotoxicity of arene ruthenium metalla-rectangles incorporating bis-pyridyl diimide linkers,” Journal of Organometallic Chemistry, vol. 815-816, pp. 53-58, 2016.
  • [7] A. Grozav, V. Miclaus, O. Vostinaru, S. Ghibu, C. Berce, I. Rotar, C. Mogosan, B. Therrien, F. Loghin and D. Popa, “Acute toxicity evaluation of a thiazolo arene ruthenium (II) complex 2 in rats,” Regulatory Toxicology and Pharmacology, vol. 80, pp. 233-240, 2016.
  • [8] O. Renier, C. Deacon-Price, J. E. B. Peters, K. Nurekeyeva, C. Russon, S. Dyson, S. Ngubane, J. Baumgartner, P. J. Dyson, T. Riedel, H. Chiririwa and B. Blom, “Synthesis and in vitro (anticancer) evaluation of η6-arene ruthenium complexes bearing stannyl ligands,” Inorganics, vol. 5, no. 4, pp. 1-13, 2017.
  • [9] W. Kandioller, C. G. Hartinger, A. A. Nazarov, J. Kasser, R. John, M. A. Jakupec, V. B. Arion, P. J. Dyson and B. K. Keppler, “Tuning the anticancer activity of maltol-derived ruthenium complexes by derivatization of the 3-hydroxy-4-pyrone moiety,” Journal of Organometallic Chemistry, vol. 694, no. 6, pp. 922-929, 2009.
  • [10] N. Mohan, M. K. M. Subarkhan and R. Ramesh, “Synthesis, antiproliferative activity and apoptosis-promoting effects of arene ruthenium(II) complexes with N, O chelating ligands,” Journal of Organometallic Chemistry, vol. 859, pp. 124-131, 2018.
  • [11] E. Orhan, A. Garci, T. Riedel, M. Saudani, P. J. Dyson and B. Therrien, “Cytotoxic double arene ruthenium metalla-cycles that overcome cisplatin resistance,” Journal of Organometallic Chemistry, vol. 803, pp. 39-44, 2016.
  • [12] C. S. Allardyce and P. J. Dyson, “Ruthenium in medicine: Current clinical uses and future prospects,” Platin. Met. Rev., vol. 45, no. 2, pp. 62–69, 2001.
  • [13] I. Kostova, “Ruthenium complexes as anticancer agents,” Curr. Med. Chem., vol. 13, pp. 1085–1107, 2006.
  • [14] C. S. Allardyce, A. Dorcier, C. Scolaro, and P. J. Dyson, “Development of organometallic (organo-transition metal) pharmaceuticals,” Applied Organometallic Chemistry, vol. 19, pp. 1–10, 2005.
  • [15] E. Orhan, A. Garci, B. Therrien, “Flexible arene ruthenium metalla-prisms,” Inorganica Chimica Acta, vol. 438, pp. 5–9, 2015.
  • [16] A. Garci, J. P. Mbakidi, V. Chaleix, V. Sol, E. Orhan and B. Therrien, “Tunable arene ruthenium metallaprisms to transport, shield, and release porphin in cancer cells,” Organometallics, vol. 34, pp. 4138−4146, 2015.
  • [17] A. Garci, A. A. Dobrov, T. Riedel, E. Orhan, P. J. Dyson, V. B. Arion and B. Therrien, “Strategy to optimize the biological activity of arene ruthenium metalla-assemblies,” Organometallics, vol. 33, pp. 3813−3822, 2014.
  • [18] U. K. Mazumder, M. Gupta, S. S. Karki, S. Bhattacharya, S. Rathinasamya and T. Sivakumar, “Synthesis and pharmacological activities of some mononuclear Ru(II) complexes,” Bioorganic & Medicinal Chemistry, vol.13, pp. 5766–5773, 2005.
  • [19] G. R. Jadhav, S. Sinha, M. Chhabra and P. Paira, “Synthesis of novel anticancer ruthenium-arene pyridinylmethylene scaffolds via three-component reaction,” Bioorganic & Medicinal Chemistry, vol. 26, no. 11, pp. 2695-2700, 2016.
  • [20] G. Süss-Fink, “Water-soluble arene ruthenium complexes: From serendipity to catalysis and drug design,” Journal of Organometallic Chemistry, vol. 751, pp. 2–19, 2014.
  • [21] H. Küçükbay, R. Durmaz, E. Orhan and S. Günal, “Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds,” Farmaco, vol. 58, pp. 431–437, 2003.
  • [22] H. Küçükbay, S. Günal, E. Orhan and R. Durmaz, “Synthesis and antimicrobial activities of some transition metal benzimidazole complexes,” Asian Journal of Chemistry, vol. 22, pp. 7376–7382, 2010.
  • [23] T. Lazarevic, A. Rilak, Z. D. Bugarcic, “Platinum, palladium, gold and ruthenium complexes as anticancer agents: Current clinical uses, cytotoxicity studies and future perspectives,” European Journal of Medicinal Chemistry, vol. 142, pp. 8-31, 2017.
  • [24] Ü. Ergun, “ONO ve ONNO tipindeki schiff bazlarının geçiş metalleri komplekslerinin termal bozunma tepkimelerinde kinetik parametrelerinin belirlenmesi ve bazı koordinasyon bağ enerjilerinin hesaplanması,” Doktora tezi, Kimya Bölümü, Ankara Üniversitesi, Ankara, Türkiye, 2009.
  • [25] M. A. Bennett and A. K. Smith, “Arene Ruthenium ( II ) Complexes formed by dehydrogenation of cyclo-hexadienes with ruthenium( III) trichloride,” Journal of the Chemical Society, pp. 233–241, 1974.
  • [26] P. Jogi, KVTS P. Kumar, “Studies on DNA cleavage and antimicrobial screening of transition metal complexes of a schiff base derived from 2-(Aminomethyl)- benzimidazole and p-chloro benzaldehyde,” Journal of Chemical and Pharmaceutical Research, vol. 4, no. 2, pp. 1389-1397, 2012.
  • [27] G. Kumaravel, N. Raman, “A treatise on benzimidazole based Schiff base metal(II) complexes accentuating their biological efficacy: Spectroscopic evaluation of DNA interactions, DNA cleavage and antimicrobial screening,” Materials Science and Engineering: C, vol. 70, no. 1, pp. 184-194, 2017.
  • [28] A. Grozav, L. I. Găină, V. Pileczki, O. Crisan, L. Silaghi-Dumitrescu, B. Therrien, V. Zaharia and I. Berindan-Neagoe, “The synthesis and antiproliferative activities of new arylidene-hydrazinyl-thiazole derivatives,” International Journal of Molecular Sciences, vol. 15, pp. 22059-22072, 2014.
  • [29] A. Grozav, O. Balacescu, L. Balacescu, T. Cheminel, I. Berindan-Neagoe and B. Therrien, “Synthesis, anticancer activity, and genome profiling of thiazolo arene ruthenium complexes,” Journal of Medicinal Chemistry, vol. 58, pp. 8475−8490, 2015.
  • [30] N.K. Kar, M.K. Singh , R.A. Lal, “Synthesis and spectral studies on monometallic ruthenium (III) complexes of N-(2-hydroxysalicyliden-1-yl)methylenebenzoylhydrazide,” Arabian Journal of Chemistry, vol. 10, pp. 76–80, 2017.
  • [31] M. U. Rehman, M. Imran, M. Arif, M. Farooq, “Metal-based antimicrobial agents: synthesis, characterization and biological studies of mannich base derivatives of benzimidazole and their metal complexes,” Science Journal of Chemistry, vol. 1, no. 5, pp. 56-66, 2013.
  • [32] M. Akkurt, S. Öztürk, H. Küçükbay, E. Orhan, O. Büyükgüngör, “1-ethyl-3-(2-phenylethyl) benzimidazole-2-selone,” Acta Cryst., vol. 60, pp. 1263-1265, 2004.
  • [33] M. Akkurt, S. Öztürk, H. Küçükbay, E. Orhan, O. Büyükgüngör, “1, 3-bis (2-phenylethyl) benzimidazolium-2-dithiocarboxylate,” Acta Cryst., vol. 60, pp. 219-221, 2004.
  • [34] S. Türktekin, M. Akkurt, E. Orhan, F. Z. Küçükbay, H. Küçükbay, O. Büyükgüngör, “Dichlorobis [1-(2-ethoxyethyl)-1H-benzimidazole-κN3] cobalt (II),” Acta Cryst., vol. 60, pp. 1220-1222, 2004.
  • [35] M. Akkurt, S. Karaca, H. Küçükbay, E. Orhan, O. Büyükgüngör, “Dichlorobis [1-(2-ethoxyethyl)-1H-benzimidazole-κN3] nickel (II),” Acta Cryst., vol. 61, pp. 41-43, 2005.
  • [36] S. Ö. Yıldırım, M Akkurt, H Küçükbay, E Orhan, O. Büyükgüngör, “6-Nitro-1-(2-phenylethyl)-1H-benzimidazole,” Acta Cryst., vol. 61, pp. 2038-2039, 2005.
  • [37] Ş. Pınar, M. Akkurt, H. Küçükbay, E. Orhan, O. Büyükgüngör, “Bis [1-(but-2-enyl)-5-nitro-1H-benzimidazole-κN3] dichlorocobalt (II),” Acta Cryst., vol. 62, pp. 1663-1665, 2006.
  • [38] M. Akkurt, S. Ö. Yıldırım, E. Orhan, H. Küçükbay, O. Büyükgüngör, “1-methoxyethyl-5-nitrobenzimidazole,” Acta Cryst., vol. 61, pp. 2804-2805, 2005.
  • [39] M. Akkurt, S. Karaca, H. Küçükbay, E. Orhan, O. Büyükgüngör, “1-benzyl-3-(2-phenethyl) benzimidazolium bromide monohydrate,” Acta Cryst., vol. 61, pp. 2452-2454, 2005.

Synthesis and Characterization of Bioactive New Benzimidazole Arene Ruthenium Organometallic Compound

Year 2020, , 1020 - 1032, 31.01.2020

Enes Hakkı Uluçay , Ersin Orhan

https://doi.org/10.29130/dubited.656633

Abstract

In this study, [(η6-p-cymene)Ru(L2)Cl]CI bioactive benzimidazole arene ruthenium organometallic compound, reacting Salicylaldehyde with 2-(Aminomethyl)benzimidazole dihydrochloride, followed by the addition of the corresponding [Ru(p-cymene)chloride]2. The bioactive benzimidazole arene ruthenium organometallic compound was characterized by standard techniques including UV-VIS, IR, ESI-MS, 1H NMR, 13C NMR spectroscopy. Thermal decomposition measurement data of arene ruthenium compound were examined. These measurements were made by Differential thermal analysis (DTA) and Thermogravimetric analysis (TGA) techniques.

Keywords

Arene ruthenium Benzimidazole Organometallic chemistry Thermal decomposition Bioactive Synthesis

Project Number

2017.05.03.620

References

  • [1] M. J. Hannon, “Metal-based anticancer drugs: From a past anchored in platinum chemistry to a post-genomic future of diverse chemistry and biology,” Pure and Applied Chemistry, vol. 79, no. 12, pp. 2243–2261, 2007.
  • [2] S. Ghosh, “Cisplatin: The first metal based anticancer drug,” Bioorganic Chemistry, vol. 88, no. 1295, pp.1-20, 2019.
  • [3] A. A. Nazarov, C. G. Hartinger and P. J. Dyson, “Opening the lid on piano-stool complexes: An account of ruthenium(II)-arene complexes with medicinal applications,” Journal of Organometallic Chemistry, vol. 751, pp. 251-260, 2014.
  • [4] L. A. Malley, “Cisplatin,” in Encyclopedia of Toxicology, 3rd ed., vol. 1, National Library of Medicine, Bethesda, USA, 2005, pp. 614-616.
  • [5] E. Orhan, A. Garci and B. Therrien, “Coordination-driven self-assembly of arene ruthenium metalla-rectangles,” Inorganica Chimica Acta, vol. 461, pp. 78–83, 2017.
  • [6] E. Orhan, A. Garci, T. Riedel, P. J. Dyson and B. Therrien, “Cytotoxicity of arene ruthenium metalla-rectangles incorporating bis-pyridyl diimide linkers,” Journal of Organometallic Chemistry, vol. 815-816, pp. 53-58, 2016.
  • [7] A. Grozav, V. Miclaus, O. Vostinaru, S. Ghibu, C. Berce, I. Rotar, C. Mogosan, B. Therrien, F. Loghin and D. Popa, “Acute toxicity evaluation of a thiazolo arene ruthenium (II) complex 2 in rats,” Regulatory Toxicology and Pharmacology, vol. 80, pp. 233-240, 2016.
  • [8] O. Renier, C. Deacon-Price, J. E. B. Peters, K. Nurekeyeva, C. Russon, S. Dyson, S. Ngubane, J. Baumgartner, P. J. Dyson, T. Riedel, H. Chiririwa and B. Blom, “Synthesis and in vitro (anticancer) evaluation of η6-arene ruthenium complexes bearing stannyl ligands,” Inorganics, vol. 5, no. 4, pp. 1-13, 2017.
  • [9] W. Kandioller, C. G. Hartinger, A. A. Nazarov, J. Kasser, R. John, M. A. Jakupec, V. B. Arion, P. J. Dyson and B. K. Keppler, “Tuning the anticancer activity of maltol-derived ruthenium complexes by derivatization of the 3-hydroxy-4-pyrone moiety,” Journal of Organometallic Chemistry, vol. 694, no. 6, pp. 922-929, 2009.
  • [10] N. Mohan, M. K. M. Subarkhan and R. Ramesh, “Synthesis, antiproliferative activity and apoptosis-promoting effects of arene ruthenium(II) complexes with N, O chelating ligands,” Journal of Organometallic Chemistry, vol. 859, pp. 124-131, 2018.
  • [11] E. Orhan, A. Garci, T. Riedel, M. Saudani, P. J. Dyson and B. Therrien, “Cytotoxic double arene ruthenium metalla-cycles that overcome cisplatin resistance,” Journal of Organometallic Chemistry, vol. 803, pp. 39-44, 2016.
  • [12] C. S. Allardyce and P. J. Dyson, “Ruthenium in medicine: Current clinical uses and future prospects,” Platin. Met. Rev., vol. 45, no. 2, pp. 62–69, 2001.
  • [13] I. Kostova, “Ruthenium complexes as anticancer agents,” Curr. Med. Chem., vol. 13, pp. 1085–1107, 2006.
  • [14] C. S. Allardyce, A. Dorcier, C. Scolaro, and P. J. Dyson, “Development of organometallic (organo-transition metal) pharmaceuticals,” Applied Organometallic Chemistry, vol. 19, pp. 1–10, 2005.
  • [15] E. Orhan, A. Garci, B. Therrien, “Flexible arene ruthenium metalla-prisms,” Inorganica Chimica Acta, vol. 438, pp. 5–9, 2015.
  • [16] A. Garci, J. P. Mbakidi, V. Chaleix, V. Sol, E. Orhan and B. Therrien, “Tunable arene ruthenium metallaprisms to transport, shield, and release porphin in cancer cells,” Organometallics, vol. 34, pp. 4138−4146, 2015.
  • [17] A. Garci, A. A. Dobrov, T. Riedel, E. Orhan, P. J. Dyson, V. B. Arion and B. Therrien, “Strategy to optimize the biological activity of arene ruthenium metalla-assemblies,” Organometallics, vol. 33, pp. 3813−3822, 2014.
  • [18] U. K. Mazumder, M. Gupta, S. S. Karki, S. Bhattacharya, S. Rathinasamya and T. Sivakumar, “Synthesis and pharmacological activities of some mononuclear Ru(II) complexes,” Bioorganic & Medicinal Chemistry, vol.13, pp. 5766–5773, 2005.
  • [19] G. R. Jadhav, S. Sinha, M. Chhabra and P. Paira, “Synthesis of novel anticancer ruthenium-arene pyridinylmethylene scaffolds via three-component reaction,” Bioorganic & Medicinal Chemistry, vol. 26, no. 11, pp. 2695-2700, 2016.
  • [20] G. Süss-Fink, “Water-soluble arene ruthenium complexes: From serendipity to catalysis and drug design,” Journal of Organometallic Chemistry, vol. 751, pp. 2–19, 2014.
  • [21] H. Küçükbay, R. Durmaz, E. Orhan and S. Günal, “Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds,” Farmaco, vol. 58, pp. 431–437, 2003.
  • [22] H. Küçükbay, S. Günal, E. Orhan and R. Durmaz, “Synthesis and antimicrobial activities of some transition metal benzimidazole complexes,” Asian Journal of Chemistry, vol. 22, pp. 7376–7382, 2010.
  • [23] T. Lazarevic, A. Rilak, Z. D. Bugarcic, “Platinum, palladium, gold and ruthenium complexes as anticancer agents: Current clinical uses, cytotoxicity studies and future perspectives,” European Journal of Medicinal Chemistry, vol. 142, pp. 8-31, 2017.
  • [24] Ü. Ergun, “ONO ve ONNO tipindeki schiff bazlarının geçiş metalleri komplekslerinin termal bozunma tepkimelerinde kinetik parametrelerinin belirlenmesi ve bazı koordinasyon bağ enerjilerinin hesaplanması,” Doktora tezi, Kimya Bölümü, Ankara Üniversitesi, Ankara, Türkiye, 2009.
  • [25] M. A. Bennett and A. K. Smith, “Arene Ruthenium ( II ) Complexes formed by dehydrogenation of cyclo-hexadienes with ruthenium( III) trichloride,” Journal of the Chemical Society, pp. 233–241, 1974.
  • [26] P. Jogi, KVTS P. Kumar, “Studies on DNA cleavage and antimicrobial screening of transition metal complexes of a schiff base derived from 2-(Aminomethyl)- benzimidazole and p-chloro benzaldehyde,” Journal of Chemical and Pharmaceutical Research, vol. 4, no. 2, pp. 1389-1397, 2012.
  • [27] G. Kumaravel, N. Raman, “A treatise on benzimidazole based Schiff base metal(II) complexes accentuating their biological efficacy: Spectroscopic evaluation of DNA interactions, DNA cleavage and antimicrobial screening,” Materials Science and Engineering: C, vol. 70, no. 1, pp. 184-194, 2017.
  • [28] A. Grozav, L. I. Găină, V. Pileczki, O. Crisan, L. Silaghi-Dumitrescu, B. Therrien, V. Zaharia and I. Berindan-Neagoe, “The synthesis and antiproliferative activities of new arylidene-hydrazinyl-thiazole derivatives,” International Journal of Molecular Sciences, vol. 15, pp. 22059-22072, 2014.
  • [29] A. Grozav, O. Balacescu, L. Balacescu, T. Cheminel, I. Berindan-Neagoe and B. Therrien, “Synthesis, anticancer activity, and genome profiling of thiazolo arene ruthenium complexes,” Journal of Medicinal Chemistry, vol. 58, pp. 8475−8490, 2015.
  • [30] N.K. Kar, M.K. Singh , R.A. Lal, “Synthesis and spectral studies on monometallic ruthenium (III) complexes of N-(2-hydroxysalicyliden-1-yl)methylenebenzoylhydrazide,” Arabian Journal of Chemistry, vol. 10, pp. 76–80, 2017.
  • [31] M. U. Rehman, M. Imran, M. Arif, M. Farooq, “Metal-based antimicrobial agents: synthesis, characterization and biological studies of mannich base derivatives of benzimidazole and their metal complexes,” Science Journal of Chemistry, vol. 1, no. 5, pp. 56-66, 2013.
  • [32] M. Akkurt, S. Öztürk, H. Küçükbay, E. Orhan, O. Büyükgüngör, “1-ethyl-3-(2-phenylethyl) benzimidazole-2-selone,” Acta Cryst., vol. 60, pp. 1263-1265, 2004.
  • [33] M. Akkurt, S. Öztürk, H. Küçükbay, E. Orhan, O. Büyükgüngör, “1, 3-bis (2-phenylethyl) benzimidazolium-2-dithiocarboxylate,” Acta Cryst., vol. 60, pp. 219-221, 2004.
  • [34] S. Türktekin, M. Akkurt, E. Orhan, F. Z. Küçükbay, H. Küçükbay, O. Büyükgüngör, “Dichlorobis [1-(2-ethoxyethyl)-1H-benzimidazole-κN3] cobalt (II),” Acta Cryst., vol. 60, pp. 1220-1222, 2004.
  • [35] M. Akkurt, S. Karaca, H. Küçükbay, E. Orhan, O. Büyükgüngör, “Dichlorobis [1-(2-ethoxyethyl)-1H-benzimidazole-κN3] nickel (II),” Acta Cryst., vol. 61, pp. 41-43, 2005.
  • [36] S. Ö. Yıldırım, M Akkurt, H Küçükbay, E Orhan, O. Büyükgüngör, “6-Nitro-1-(2-phenylethyl)-1H-benzimidazole,” Acta Cryst., vol. 61, pp. 2038-2039, 2005.
  • [37] Ş. Pınar, M. Akkurt, H. Küçükbay, E. Orhan, O. Büyükgüngör, “Bis [1-(but-2-enyl)-5-nitro-1H-benzimidazole-κN3] dichlorocobalt (II),” Acta Cryst., vol. 62, pp. 1663-1665, 2006.
  • [38] M. Akkurt, S. Ö. Yıldırım, E. Orhan, H. Küçükbay, O. Büyükgüngör, “1-methoxyethyl-5-nitrobenzimidazole,” Acta Cryst., vol. 61, pp. 2804-2805, 2005.
  • [39] M. Akkurt, S. Karaca, H. Küçükbay, E. Orhan, O. Büyükgüngör, “1-benzyl-3-(2-phenethyl) benzimidazolium bromide monohydrate,” Acta Cryst., vol. 61, pp. 2452-2454, 2005.
There are 39 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Enes Hakkı Uluçay 0000-0002-9552-1372

Ersin Orhan 0000-0002-5461-1005

Project Number 2017.05.03.620
Publication Date January 31, 2020
Published in Issue Year 2020

Cite

APA Uluçay, E. H., & Orhan, E. (2020). Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi ve Karakterizasyonu. Duzce University Journal of Science and Technology, 8(1), 1020-1032. https://doi.org/10.29130/dubited.656633
AMA Uluçay EH, Orhan E. Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi ve Karakterizasyonu. DÜBİTED. January 2020;8(1):1020-1032. doi:10.29130/dubited.656633
Chicago Uluçay, Enes Hakkı, and Ersin Orhan. “Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi Ve Karakterizasyonu”. Duzce University Journal of Science and Technology 8, no. 1 (January 2020): 1020-32. https://doi.org/10.29130/dubited.656633.
EndNote Uluçay EH, Orhan E (January 1, 2020) Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi ve Karakterizasyonu. Duzce University Journal of Science and Technology 8 1 1020–1032.
IEEE E. H. Uluçay and E. Orhan, “Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi ve Karakterizasyonu”, DÜBİTED, vol. 8, no. 1, pp. 1020–1032, 2020, doi: 10.29130/dubited.656633.
ISNAD Uluçay, Enes Hakkı - Orhan, Ersin. “Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi Ve Karakterizasyonu”. Duzce University Journal of Science and Technology 8/1 (January 2020), 1020-1032. https://doi.org/10.29130/dubited.656633.
JAMA Uluçay EH, Orhan E. Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi ve Karakterizasyonu. DÜBİTED. 2020;8:1020–1032.
MLA Uluçay, Enes Hakkı and Ersin Orhan. “Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi Ve Karakterizasyonu”. Duzce University Journal of Science and Technology, vol. 8, no. 1, 2020, pp. 1020-32, doi:10.29130/dubited.656633.
Vancouver Uluçay EH, Orhan E. Biyoaktif Yeni Benzimidazol Aren Rutenyum Organometalik Bileşiğinin Sentezi ve Karakterizasyonu. DÜBİTED. 2020;8(1):1020-32.