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1-(4-Klorobenzil)-2-(piridin-2-yl) benzimidazol Biyoaktif Organik Bileşiğinin Sentezi ve Karakterizasyonu

Year 2023, Volume: 11 Issue: 2, 775 - 786, 30.04.2023
https://doi.org/10.29130/dubited.1104207

Abstract

Bu çalışmada 1-(4-klorobenzil)-2-(piridin-2-yl)-1H-benzo[d]imidazol genel formülüne sahip organik bileşiği, 2- (2-piridil)benzimidazol’ün potasyum karbonat (K2CO3) ile reaksiyona sokulması ve ardından 4-klorobenzil klorür ile tepkimesi sonucu hazırlandı. Sentezlenen organik bileşik IR, UV-VIS, 1H, 13C NMR spektroskopisi ve ESI-MS spektroskopisi dahil standart tekniklerle karakterize edildi. Benzimidazol türevi bileşiğinin termal bozunma ölçüm verileri incelendi. Bu ölçümler termogravimetrik analiz (TGA) ve diferansiyel termal analiz
(DTA) teknikleri ile yapıldı ve floresans spektrum değerleri kaydedildi.

Supporting Institution

Düzce Üniversitesi

Project Number

2022.05.03.1304

Thanks

Bu çalışma Düzce Üniversitesi Bilimsel Araştırma Projeleri tarafından desteklenmiştir (Proje no: 2022.05.03.1304).

References

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  • [22] L. Gundogdu, M. Kose, S. Takeuchi, Y. Yokoyama, and E. Orhan, “Synthesis, photochromic and fluorescence properties of new bithiazole-containing diarylethenes as cation sensors,” J. Lumin., vol. 203, no. June, pp. 568–575, Nov. 2018, doi: 10.1016/j.jlumin.2018.06.014.
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Synthesis and Characterization of 1-(4-Chlorobenzyl)-2-(pyridine-2- yl)benzimidazole Bioactive Organic Compound

Year 2023, Volume: 11 Issue: 2, 775 - 786, 30.04.2023
https://doi.org/10.29130/dubited.1104207

Abstract

In this study, the organic compound with the general formula 1-(4-chlorobenzyl)-2-(pyridin-2-yl)-1H- benzo[d]imidazole was reacted with 2-(2-pyridyl)benzimidazole with potassium carbonate (K2CO3). It was prepared subsequent reaction with 4-chlorobenzyl chloride. The synthesized organic compound was characterized by standard techniques including IR, UV-VIS, 1H, 13C NMR spectroscopy and ESI-MS spectroscopy. Thermal degradation measurement data of benzimidazole derivative compound were examined. These measurements were made with thermogravimetric analysis (TGA) and differential thermal analysis (DTA) techniques and fluorescence
Spectrum values were recorded.

Project Number

2022.05.03.1304

References

  • [1] E. Orhan, · Ece Ergun, · Koray Şarkaya, and · Ümit Ergun, “A Novel Benzimidazole-Based Chemosensor for Fluorometric Determination of Zinc Ions,” J. Fluoresc., vol. 1, p. 3, doi: 10.1007/s10895-021-02818-w.
  • [2] A. Kamil et al., “Synthesis, structure–activity relationship and antinociceptive activities of some 2-(2′-pyridyl) benzimidazole derivatives,” Med. Chem. Res., vol. 25, no. 6, pp. 1216–1228, 2016, doi: 10.1007/s00044-016-1560-8.
  • [3] M. Akkurt, S. Öztürk, H. Küçükbay, E. Orhan, and O. Büyükgüngör, “1,3-Bis(2- phenylethyl)benzimidazolium-2-dithiocarboxylate,” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 60, no. 2, pp. 219–222, 2004, doi: 10.1107/S160053680400073X.
  • [4] M. Kose and E. Orhan, “Studies on photochromic benzimidazol[1,2a]pyrrolidin-2-ones from the condensation of 2-methyl-3-benzothienylethylidene- (isopropylidene)succinic anhydride with 1,2-diaminobenzenes,” J. Photochem. Photobiol. A Chem., vol. 177, no. 2–3, pp. 170–176, Jan. 2006, doi: 10.1016/j.jphotochem.2005.05.022.
  • [5] M. Akkurt, S. Karaca, H. Küçükbay, E. Orhan, and O. Büyükgüngör, “Dichlorobis[1-(2- ethoxyethyl)-1H-benz-imidazole-κN 3]nickel(II),” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 61, no. 1, 2005, doi: 10.1107/S1600536804031356.
  • [6] S. Türktekin, M. Akkurt, E. Orhan, F. Zehra Küçükbay, H. Küçükbay, and O. Büyükgüngör, “Dichlorobis[1-(2-ethoxyethyl)-1H-benzimidazole-κ3] cobalt(II),” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 60, no. 9, pp. 1220–1223, 2004, doi: 10.1107/S1600536804018835.
  • [7] M. Gopalakrishnan, P. Sureshkumar, J. Thanusu, V. Kanagarajan, R. Govindaraju, and G. Jayasri, “Journal of Enzyme Inhibition and Medicinal Chemistry A convenient ‘one-pot’ synthesis and in vitro microbiological evaluation of novel 2,7-diaryl-[1,4]-diazepan-5-ones,” doi: 10.1080/14756360701270618.
  • [8] M. Akkurt, S. Öztürk, H. Küçükbay, E. Orhan, and O. Büyükgüngör, “1-Ethyl-3-(2- phenylethyl)benzimidazole-2-selone,” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 60, no. 7, pp. 1263–1266, 2004, doi: 10.1107/S1600536804014977.
  • [9] Z. Kazimierczuk, M. Andrzejewska, J. Kaustova, and V. Klimešova, “Synthesis and antimycobacterial activity of 2-substituted halogenobenzimidazoles,” Eur. J. Med. Chem., vol. 40, no. 2, pp. 203–208, Feb. 2005, doi: 10.1016/J.EJMECH.2004.10.004.
  • [10] E. Orhan, A. Garci, T. Riedel, P. J. Dyson, and B. Therrien, “Cytotoxicity of arene ruthenium metalla-rectangles incorporating bis-pyridyl diimide linkers,” J. Organomet. Chem., vol. 815– 816, 2016, doi: 10.1016/j.jorganchem.2016.05.004.
  • [11] H. Küçükbay, S. Günal, E. Orhan, and R. Durmaz, “Synthesis and antimicrobial activities of some transition metal benzimidazole complexes,” Asian J. Chem., vol. 22, no. 9, pp. 7376–7382, 2010.
  • [12] S. Ö. Yildirim, M. Akkurt, H. Küçükbay, E. Orhan, and O. Büyükgüngör, “6-Nitro-1-(2- phenylethyl)-1H-benzimidazole,” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 61, no. 7, pp. o2038–o2039, Jul. 2005, doi: 10.1107/S1600536805017502/DN6224ISUP2.HKL.
  • [13] Z. Saeed Saify et al., “2-(2 0-Pyridyl) benzimidazole derivatives and their urease inhibitory activity,” doi: 10.1007/s00044-014-1015-z.
  • [14] E. Orhan, A. Garci, and B. Therrien, “Flexible arene ruthenium metalla-prisms,” Inorganica Chim. Acta, vol. 438, pp. 5–9, 2015, doi: 10.1016/j.ica.2015.09.002.
  • [15] M. Kose, E. Orhan, K. Suzuki, A. Tutar, C. S. Ünlü, and Y. Yokoyama, “Preparation and photochromic properties of 2,3-bisarylbenz[f]indenones,” J. Photochem. Photobiol. A Chem., vol. 257, 2013, doi: 10.1016/j.jphotochem.2013.01.012.
  • [16] Ş. Pinar, M. Akkurt, H. Küçükbay, E. Orhan, and O. Büyükgüngör, “Bis[1-(but-2-enyl)-5-nitro-1H-benzimidazole-κN3]- dichlorocobalt(II),” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 62, no. 7, 2006, doi: 10.1107/S160053680602352X.
  • [17] M. Akkurt, S. Karaca, H. Küçükbay, E. Orhan, and O. Büyükgüngör, “1-Benzyl-3-(2- phenethyl)benzimidazolium bromide monohydrate,” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 61, no. 8, 2005, doi: 10.1107/S1600536805021653.
  • [18] M. Akkurt, S. Ö. S. Ö. Yildirim, E. Orhan, H. Küçükbay, and O. Büyükgüngör, “1- Methoxyethyl-5-Nitrobenzimidazole,” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 61, no. 9, pp. 10–12, 2005, doi: 10.1107/S1600536805024591.
  • [19] E. Orhan, A. Garci, and B. Therrien, “Coordination-driven self-assembly of arene ruthenium metalla-rectangles,” Inorganica Chim. Acta, vol. 461, 2017, doi: 10.1016/j.ica.2017.01.033.
  • [20] M. Köse and E. Orhan, “Comparison of photochromic properties and thermal stabilities of fulgide, fulgimide, and benzimidazole[1,2-a]pyrrolidine-2-one derivatives,” Turkish J. Chem., vol. 33, no. 5, 2009, doi: 10.3906/kim-0805-1.
  • [21] M. Kose, E. Orhan, and O. Büyükgüngör, “Synthesis of novel photochromic methyl cyanoacetate-condensed fulgide derivatives,” J. Photochem. Photobiol. A Chem., vol. 188, no. 2–3, pp. 358–363, May 2007, doi: 10.1016/j.jphotochem.2006.12.036.
  • [22] L. Gundogdu, M. Kose, S. Takeuchi, Y. Yokoyama, and E. Orhan, “Synthesis, photochromic and fluorescence properties of new bithiazole-containing diarylethenes as cation sensors,” J. Lumin., vol. 203, no. June, pp. 568–575, Nov. 2018, doi: 10.1016/j.jlumin.2018.06.014.
  • [23] E. Orhan, L. Gundogdu, M. Kose, and Y. Yokoyama, “Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones,” J. Photochem. Photobiol. A Chem., vol. 314, pp. 164–170, Jan. 2016, doi: 10.1016/j.jphotochem.2015.08.025.
  • [24] M. Akkurt, S. Öztürk, H. Küçükbay, E. Orhan, and O. Büyükg̈ ngör, “1-Ethyl-4-phenylethyl-1,4- dihydroquinoxaline-2,3-dione,” Acta Crystallogr. Sect. E Struct. Reports Online, vol. 60, no. 7, pp. 1266–1269, 2004, doi: 10.1107/S1600536804014989.
  • [25] E. Orhan, G. Dülger, · Merve Alpay, · Nilüfer Öksüz, and B. Dülger, “Synthesis, antimicrobial and antiproliferative activities of new self-assembly benzimidazole-bridged aren ruthenium rectangles in human breast cancer cells,” J. Incl. Phenom. Macrocycl. Chem., vol. 102, pp. 45– 54, 2022, doi: 10.1007/s10847-021-01099-x.
  • [26] M. Taha et al., “Synthesis of new 1,2-disubstituted benzimidazole analogs as potent inhibitors of β-Glucuronidase and in silico study,” Arab. J. Chem., vol. 15, no. 1, p. 103505, 2022, doi: 10.1016/j.arabjc.2021.103505.
  • [27] P. Keller et al., “An Antifungal Benzimidazole Derivative Inhibits Ergosterol Biosynthesis and Reveals Novel Sterols,” 2015, doi: 10.1128/AAC.00640-15.
  • [28] B. Kahveci, F. Yilmaz, E. Menteşe, M. Özil, and Ş. A. Karaoǧlu, “Microwave-assisted synthesis of some novel benzimidazole derivatives containing imine function and evaluation of their antimicrobial activity,” J. Heterocycl. Chem., vol. 51, no. 4, pp. 982–990, 2014, doi: 10.1002/JHET.1593.
  • [29] A. Welsh, L. I. Rylands, V. B. Arion, S. Prince, and G. S. Smith, “Synthesis and antiproliferative activity of benzimidazole-based, trinuclear neutral cyclometallated and cationic, N^N-chelated ruthenium(ii) complexes,” Dalt. Trans., vol. 49, no. 4, pp. 1143–1156, 2020, doi: 10.1039/c9dt03902c.
  • [30] A. Schroeder et al., “Treating metastatic cancer with nanotechnology,” Nat. Rev. Cancer, 2012, doi: 10.1038/nrc3180.
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There are 33 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Meltem Oğuz 0000-0002-9435-9529

Ersin Orhan 0000-0002-5461-1005

Project Number 2022.05.03.1304
Publication Date April 30, 2023
Published in Issue Year 2023 Volume: 11 Issue: 2

Cite

APA Oğuz, M., & Orhan, E. (2023). 1-(4-Klorobenzil)-2-(piridin-2-yl) benzimidazol Biyoaktif Organik Bileşiğinin Sentezi ve Karakterizasyonu. Düzce Üniversitesi Bilim Ve Teknoloji Dergisi, 11(2), 775-786. https://doi.org/10.29130/dubited.1104207
AMA Oğuz M, Orhan E. 1-(4-Klorobenzil)-2-(piridin-2-yl) benzimidazol Biyoaktif Organik Bileşiğinin Sentezi ve Karakterizasyonu. DUBİTED. April 2023;11(2):775-786. doi:10.29130/dubited.1104207
Chicago Oğuz, Meltem, and Ersin Orhan. “1-(4-Klorobenzil)-2-(piridin-2-Yl) Benzimidazol Biyoaktif Organik Bileşiğinin Sentezi Ve Karakterizasyonu”. Düzce Üniversitesi Bilim Ve Teknoloji Dergisi 11, no. 2 (April 2023): 775-86. https://doi.org/10.29130/dubited.1104207.
EndNote Oğuz M, Orhan E (April 1, 2023) 1-(4-Klorobenzil)-2-(piridin-2-yl) benzimidazol Biyoaktif Organik Bileşiğinin Sentezi ve Karakterizasyonu. Düzce Üniversitesi Bilim ve Teknoloji Dergisi 11 2 775–786.
IEEE M. Oğuz and E. Orhan, “1-(4-Klorobenzil)-2-(piridin-2-yl) benzimidazol Biyoaktif Organik Bileşiğinin Sentezi ve Karakterizasyonu”, DUBİTED, vol. 11, no. 2, pp. 775–786, 2023, doi: 10.29130/dubited.1104207.
ISNAD Oğuz, Meltem - Orhan, Ersin. “1-(4-Klorobenzil)-2-(piridin-2-Yl) Benzimidazol Biyoaktif Organik Bileşiğinin Sentezi Ve Karakterizasyonu”. Düzce Üniversitesi Bilim ve Teknoloji Dergisi 11/2 (April 2023), 775-786. https://doi.org/10.29130/dubited.1104207.
JAMA Oğuz M, Orhan E. 1-(4-Klorobenzil)-2-(piridin-2-yl) benzimidazol Biyoaktif Organik Bileşiğinin Sentezi ve Karakterizasyonu. DUBİTED. 2023;11:775–786.
MLA Oğuz, Meltem and Ersin Orhan. “1-(4-Klorobenzil)-2-(piridin-2-Yl) Benzimidazol Biyoaktif Organik Bileşiğinin Sentezi Ve Karakterizasyonu”. Düzce Üniversitesi Bilim Ve Teknoloji Dergisi, vol. 11, no. 2, 2023, pp. 775-86, doi:10.29130/dubited.1104207.
Vancouver Oğuz M, Orhan E. 1-(4-Klorobenzil)-2-(piridin-2-yl) benzimidazol Biyoaktif Organik Bileşiğinin Sentezi ve Karakterizasyonu. DUBİTED. 2023;11(2):775-86.