Synthesis and Antioxidant Properties of New Benzimidazole Derivatives

Nurhan Gümrükçüoğlu

doi:10.2339/politeknik.718979

Araştırma Makalesi

Synthesis and Antioxidant Properties of New Benzimidazole Derivatives

Yıl 2021, , 1699 - 1706, 01.12.2021

Nurhan Gümrükçüoğlu

https://doi.org/10.2339/politeknik.718979

Cited By: 1

Öz

In this study, new benzimidazole derivatives were synthesized. After purity checks were made with Thin Layer Chromatography (TLC) and melting points, their structures were proved by mass spectroscopy, 1H, 13C NMR and elemental analysis technique. Antioxidant activities of the obtained materials were searched in terms of their effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, lipid peroxidation inhibition and ethoxyresorufin O-deethylase (EROD) enzyme activity. It was observed the compounds were generally moderately active in terms of DPPH radical scavenging activity and lipid peroxidation inhibition compared to the standard compound and had a good effect on EROD enzyme activity.

Anahtar Kelimeler

DPPH, EROD enzyme activity, 1,3,4-oxadiazole

Kaynakça

1. Patlevic P., Vaskov J., Svorc B., Vasko L., Svorc P., ''Reactive oxygen species and antioxidant defense in human gastrointestinal diseases'', Integrative Medicine Research, 5: 250-258, (2016). doi: 10.1016/j.imr.2016.07.004
2. Desai K. G., Desai K. R., ''Green Route for The Heterocyclization of 2-Mercaptobenzimidazole Into Β-Lactum Segment Derivatives Containing–CONH– Bridge with Benzimidazole: Screening In Vitro Antimicrobial Activity With Various Microorganisms'', Bioorganic & Medicinal Chemistry,14: 8271-8279, (2006). doi: 10.1016/j.bmc.2006.09.017
3. Vazquez G. N., Vilehis M. R., Mulia L. Y., Melendez V., Gerena L., et al., ''Synthesis and Antiprotozoal Activity of Some 2-(Trifluoromethyl)-1HBenzimidazole Bioisosteres'', European Journal of Medicinal Chemistry, 41:135-141, (2006). doi: 10.1016/j.ejmech.2005.09.00
4. Mavrova A. T., Anichina K. K., Vuchev D. I., ''Antihelminthic Activity of Some Newly Synthesized5(6)-(un)substituted-1H-Benzimidazol-2-yl-thioacetylpiperazine Derivatives'', European Journal of Medicinal Chemistry, 41:1412-1420, (2006). doi: 10.1016/j.ejmech.2006.07.005
5. Kılcıgil G. A., Altanlar N., ''Synthesis and Antifungal Properties of Some Benzimidazole Derivatives'', Turkish Journal of Chemistry, 30: 223-228, (2006).
6. Hwu J. R., Singha R., Hong S. C., Chang Y. H., Das A. R., et al., ''Synthesis of New Benzimidazole-Coumarin Conjugates as Anti-Hepatitis C Virus Agents'', Antiviral Research, 77: 157-162, (2008). doi: 10.1016/j.antiviral.2007.09.003
7. Tremblay M., Bonneau P., Bousquet Y., Deroy P., Duan J et al., ''Inhibition of HIV-1 Capsid Assembly: Optimization of the Antiviral Potency by Site Selective Modifications at N1, C2 and C16 of a 5-(5-Furan-2-yl-Pyrazol-1-yl)-1H-Benzimidazole Scaffold'', Bioorganic & Medicinal Chemistry Letters, 22: 7512-7517, (2012). doi: 10.1016/j.bmcl.2012.10.034
8. Uchida M., Chihiro M., Morita S., Yamashita H., Yamasaki K et al., ''Synthesis and Antiulcer Activity of 4-Substituted 8-[ (2-Benzimidazolyl) Sulfinylmethyl ]-1,2,3,4 -Tetrahydro quinolines and Related Compounds'', Chemical and Pharmaceutical Bulletin, 38: 1575-1586, (1990). doi: 10.1248/cpb.38.1575
9. Grassi A., Ippen J., Bruno M., Thomas G. A., ''Thiazolylamino Benzimidazole Derivative with Gastroprotective Properties in the Rat'', European Journal of Pharmacology, 195: 251-259, (1991). doi: 10.1016/0014-2999(91)90543-Y
10. Achar K. C., Hosamani K. M., Seetharamareddy H. R., ''In-Vivo Analgesic and Anti-Inflammatory Activities of Newly Synthesized Benzimidazole Derivatives'' European Journal of Medicinal Chemistry, 45: 2048-2054, (2010). doi: 0.1016/j.ejmech.2010.01.029
11.Thakurdesai P. A., Wadodkar S. G., Chopade C. T., ''Synthesis and Anti Inflammatory Activity of Some Benzimidazole-2-Carboxylic Acids'', Pharmacologyonline, 1: 314–329, (2007).
12. Iemura R., Kawashima T., Fukuda T., Ito K., Tsukamoto G., ''Synthesis of 2-(4-Substituted-1-Piperazinyl) Benzimidazoles as H1-Antihistaminic Agents'', Journal of Medicinal Chemistry, 29: 1178-1183, (1986). doi: 0022-2623/86/1829-1183$01.50/0
13. Nakano H., Inoue T., Kawasaki N., Miyataka H., Matsumoto H., et al., ''Synthesis of Benzimidazole Derivatives as Antiallergic Agents with 5-Lipoxygenase Inhibiting Action'', Chemical and Pharmaceutical Bulletin, 47:1573-1578, (1999). doi: 10.1248/cpb.47.1573
14. Naka T., ''Angiotensin II Receptor Antagonist Activities and Mode of Action of Benzimidazole-7-Carboxylic Acid Derivatives'', Nihon Rinsho, 51: 1575-1579, (1993).
15. Shingalapur R. V., Hosamani K. M., Keri R. S., ''Synthesis and Evaluation of In Vitro Anti-Microbial and Anti-Tubercular Activity of 2-Styryl Benzimidazoles'', European Journal of Medicinal Chemistry, 44: 4244-4248, (2009). doi: 10.1016/j.ejmech.2009.05.021
16. Siddiqui N., Alam M. S., Sahu M., Yar M. S., Alam O., et al., ''Antidepressant, Analgesic Activity and SAR Studies of Substituted Benzimidazoles'', Asian Journal of Pharmaceutical Research, 6: 170-174, (2016). doi: 10.5958/2231-5691.2016.00024.1
17. Hemalatha S., Ayyappan T., Shanmugam S., Nagavalli S., Kurubha T. S., ''Evaluation of antidiabetic and diuretic activity of polyherbal formulation'', Indian Journal of Traditional Knowledge, 5: 468-470, (2006).
18. Kumar J. R., Jat J. L., Pathak D. P., ''Synthesis of Benzimidazole Derivatives: as Anti-Hypertensive Agents'', E-Journal of Chemistry, 3: 278-285, (2006). doi: 10.1155/2006/765712
19. Kerimov I., Kilcigil A, G., Eke B. C., Altanlar N., Iscan M., ''Synthesis, Antifungal and Antioxidant Screening of Some Novel Benzimidazole Derivatives'', Journal of Enzyme Inhibition and Medicinal Chemistry, 22: 696-701, (2007). doi: 10.1080/14756360701228558
20. Kilcigil A. G., Kuş C., Özdamar E. D., Can B., İscan M., ''Synthesis and Antioxidant Capacities of Some New Benzimidazole Derivatives'', Archiv der Pharmazie, 340: 607–611, (2007). doi: 10.1002/ardp.200700088
21. Ateş-Alagöz Z., Kuş C., Çoban T., ''Synthesis and Antioxidant Properties of Novel Benzimidazoles Containing Substituted Indole or 1,1,4,4-Tetramethyl-1,2,3,4-Tetrahydro-Naphthalene Fragments'', Journal of Enzyme Inhibition and Medicinal Chemistry, 20: 325–331, (2005). doi: 10.1080/14756360500131706
22. Sharma R., Bali A., Chaudhari, B. B., ''Synthesis of Methanesulphonamid -Benzimidazole Derivatives as Gastro-Sparing Antiinflammatory Agents with Antioxidant Effect'', Bioorganic & Medicinal Chemistry Letters, 27: 3007–3013, (2017). doi: 10.1016/j.bmcl.2017.05.017
23. Castro A. R., Rivera I. L., Rojas L. C. A., Vazquez G., Rodríguez A. N., ''Synthesis and Preliminary Evaluation of Selected 2-Aryl-5(6)-Nitro-1H-Benzimidazole Derivatives as Potential Anticancer Agents'', Archives of Pharmacal Research, 34: 181-189, (2011). doi: 10.1007/s12272-011-0201-5
24. Demirayak S., Kayagil I., Yurttas L., ''Microwave Supported Synthesis of Some Novel 1,3-Diarylpyrazino-[1,2-A]-Benzimidazole Derivatives and Investigation of Their Anticancer Activities'', European Journal of Medicinal Chemistry, 46: 411-416, (2011). doi: 10.1016/j.ejmech.2010.11.007
25. Nail M. S., Rosario S., Frederic G., Jean-Claude G. B., ''Benzothiazole-and Benzoxazole-Substituted Pyridine-2-Carboxylates as Efficient Sensitizers of Europium Luminescence'', Inorganic Chemistry, 48: 6178–6191, (2009). doi: 10.1021/ic9005136
26. Ma X., Qui X., Jin R., Kang C., Gao L., ''Synthesis and Properties of Fluorescence Poly (Benzoxazole–Imide) s Containing Naphthalene'', High Performance Polymers, 27: 734–741, (2015). doi: 10.1177/0954008314559552
27. Myung G. C., Sang H. L., Yun U. J., Ja M. H., Suk K. C., ''Fluorescence Signaling of BF3 Species byTransformation of an ESIPT Dye to its Difluoroboron Adduct'', Sensors and Actuators B: Chemical, 251: 713–719, (2017). doi: 0.1016/j.snb.2017.05.098
28. Salahuddin M., Mazumder A., Abdullah M. M., ''Synthesis, Characterization and Antimicrobial Activity of 1,3,4-Oxadiazole Bearing 1H-Benzimidazole Derivatives'', Arabian Journal of Chemistry, 10: 503–508, (2017). doi: 10.1016/j.arabjc.2012.10.010
29. Karaali N., ''Synthesis of Some New Benzimidazole Derivatives Containing Chlorine and Investigation of Their Antioxidant and Anti-Urease Activities'', Journal of the Turkish Chemical Society Section A: Chemistry, 5: 971-980, (2018). doi: 10.18596/jotcsa.440202
30. Mochona B., Mazzio E., Gangapurum M., Mateeva N., Redda K. K., ''Synthesis of Some Benzimidazole Derivatives Bearing 1,3,4-Oxadiazole Moiety as Anticancer Agents'', Chemical Science Transactions, 4: 534–540, (2015). doi: 10.7598/cst2015.1029
31. Kapoor A., Dhiman N., ''Anticancer Evaluation of 2-Aryl Substituted Benzimidazole Derivatives Bearing 1,3,4-Oxadiazole Nucleus'', Der Pharmacia Lettre, 8: 149-156, (2016).
32. Youssif G. M., Mohamed Y. A., Salim M. T., Inagakı F., Mukai C., et al., ''Synthesis of Some Benzimidazole Derivatives Endowed with 1,2,3-Triazole as Potential Inhibitors of Hepatitis C Virus'', Acta Pharmaceutica, 66: 219-231, (2016). doi: 10.1515/acph-2016-0014
33. Shingalapur R. V., Hosamani K. M., Keri R. S., Hugar M. H., ''Derivatives of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic and DNA Cleavage Studies'', European Journal of Medicinal Chemistry, 45: 1753–1759, (2010). doi: 10.1016/j.ejmech.2010.01.007
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Synthesis and Antioxidant Properties of New Benzimidazole Derivatives

Yıl 2021, , 1699 - 1706, 01.12.2021

Nurhan Gümrükçüoğlu

https://doi.org/10.2339/politeknik.718979

Cited By: 1

Öz

Bu çalışmada yeni benzimidazol türevleri sentezlenmiştir. İnce Tabaka Kromatografisi (TLC) ve erime noktaları ile saflık kontrolleri yapıldıktan sonra yapıları kütle spektroskopisi, 1H, 13C NMR ve element analizi teknikleri ile kanıtlanmıştır. Elde edilen bileşiklerin antioksidan aktiviteleri, 2, 2-difenil-1-pikrilhidrazil (DPPH) radikal temizleme aktivitesi, lipit peroksidasyon inhibisyonu ve etoksresorufin O-deetilaz (EROD) enzim aktivitesi üzerindeki etkileri açısından araştırılmıştır. Bileşikler, standart bileşik ile karşılaştırıldığında DPPH radikal temizleme aktivitesi ve lipit peroksidasyon inhibisyonu açısından genellikle orta derecede ve EROD enzim aktivitesi üzerinde iyi bir etkiye sahip olduğu gözlenmiştir.

Anahtar Kelimeler

DPPH, EROD enzyme activity, 1,3,4-oxadiazole

Kaynakça

1. Patlevic P., Vaskov J., Svorc B., Vasko L., Svorc P., ''Reactive oxygen species and antioxidant defense in human gastrointestinal diseases'', Integrative Medicine Research, 5: 250-258, (2016). doi: 10.1016/j.imr.2016.07.004
2. Desai K. G., Desai K. R., ''Green Route for The Heterocyclization of 2-Mercaptobenzimidazole Into Β-Lactum Segment Derivatives Containing–CONH– Bridge with Benzimidazole: Screening In Vitro Antimicrobial Activity With Various Microorganisms'', Bioorganic & Medicinal Chemistry,14: 8271-8279, (2006). doi: 10.1016/j.bmc.2006.09.017
3. Vazquez G. N., Vilehis M. R., Mulia L. Y., Melendez V., Gerena L., et al., ''Synthesis and Antiprotozoal Activity of Some 2-(Trifluoromethyl)-1HBenzimidazole Bioisosteres'', European Journal of Medicinal Chemistry, 41:135-141, (2006). doi: 10.1016/j.ejmech.2005.09.00
4. Mavrova A. T., Anichina K. K., Vuchev D. I., ''Antihelminthic Activity of Some Newly Synthesized5(6)-(un)substituted-1H-Benzimidazol-2-yl-thioacetylpiperazine Derivatives'', European Journal of Medicinal Chemistry, 41:1412-1420, (2006). doi: 10.1016/j.ejmech.2006.07.005
5. Kılcıgil G. A., Altanlar N., ''Synthesis and Antifungal Properties of Some Benzimidazole Derivatives'', Turkish Journal of Chemistry, 30: 223-228, (2006).
6. Hwu J. R., Singha R., Hong S. C., Chang Y. H., Das A. R., et al., ''Synthesis of New Benzimidazole-Coumarin Conjugates as Anti-Hepatitis C Virus Agents'', Antiviral Research, 77: 157-162, (2008). doi: 10.1016/j.antiviral.2007.09.003
7. Tremblay M., Bonneau P., Bousquet Y., Deroy P., Duan J et al., ''Inhibition of HIV-1 Capsid Assembly: Optimization of the Antiviral Potency by Site Selective Modifications at N1, C2 and C16 of a 5-(5-Furan-2-yl-Pyrazol-1-yl)-1H-Benzimidazole Scaffold'', Bioorganic & Medicinal Chemistry Letters, 22: 7512-7517, (2012). doi: 10.1016/j.bmcl.2012.10.034
8. Uchida M., Chihiro M., Morita S., Yamashita H., Yamasaki K et al., ''Synthesis and Antiulcer Activity of 4-Substituted 8-[ (2-Benzimidazolyl) Sulfinylmethyl ]-1,2,3,4 -Tetrahydro quinolines and Related Compounds'', Chemical and Pharmaceutical Bulletin, 38: 1575-1586, (1990). doi: 10.1248/cpb.38.1575
9. Grassi A., Ippen J., Bruno M., Thomas G. A., ''Thiazolylamino Benzimidazole Derivative with Gastroprotective Properties in the Rat'', European Journal of Pharmacology, 195: 251-259, (1991). doi: 10.1016/0014-2999(91)90543-Y
10. Achar K. C., Hosamani K. M., Seetharamareddy H. R., ''In-Vivo Analgesic and Anti-Inflammatory Activities of Newly Synthesized Benzimidazole Derivatives'' European Journal of Medicinal Chemistry, 45: 2048-2054, (2010). doi: 0.1016/j.ejmech.2010.01.029
11.Thakurdesai P. A., Wadodkar S. G., Chopade C. T., ''Synthesis and Anti Inflammatory Activity of Some Benzimidazole-2-Carboxylic Acids'', Pharmacologyonline, 1: 314–329, (2007).
12. Iemura R., Kawashima T., Fukuda T., Ito K., Tsukamoto G., ''Synthesis of 2-(4-Substituted-1-Piperazinyl) Benzimidazoles as H1-Antihistaminic Agents'', Journal of Medicinal Chemistry, 29: 1178-1183, (1986). doi: 0022-2623/86/1829-1183$01.50/0
13. Nakano H., Inoue T., Kawasaki N., Miyataka H., Matsumoto H., et al., ''Synthesis of Benzimidazole Derivatives as Antiallergic Agents with 5-Lipoxygenase Inhibiting Action'', Chemical and Pharmaceutical Bulletin, 47:1573-1578, (1999). doi: 10.1248/cpb.47.1573
14. Naka T., ''Angiotensin II Receptor Antagonist Activities and Mode of Action of Benzimidazole-7-Carboxylic Acid Derivatives'', Nihon Rinsho, 51: 1575-1579, (1993).
15. Shingalapur R. V., Hosamani K. M., Keri R. S., ''Synthesis and Evaluation of In Vitro Anti-Microbial and Anti-Tubercular Activity of 2-Styryl Benzimidazoles'', European Journal of Medicinal Chemistry, 44: 4244-4248, (2009). doi: 10.1016/j.ejmech.2009.05.021
16. Siddiqui N., Alam M. S., Sahu M., Yar M. S., Alam O., et al., ''Antidepressant, Analgesic Activity and SAR Studies of Substituted Benzimidazoles'', Asian Journal of Pharmaceutical Research, 6: 170-174, (2016). doi: 10.5958/2231-5691.2016.00024.1
17. Hemalatha S., Ayyappan T., Shanmugam S., Nagavalli S., Kurubha T. S., ''Evaluation of antidiabetic and diuretic activity of polyherbal formulation'', Indian Journal of Traditional Knowledge, 5: 468-470, (2006).
18. Kumar J. R., Jat J. L., Pathak D. P., ''Synthesis of Benzimidazole Derivatives: as Anti-Hypertensive Agents'', E-Journal of Chemistry, 3: 278-285, (2006). doi: 10.1155/2006/765712
19. Kerimov I., Kilcigil A, G., Eke B. C., Altanlar N., Iscan M., ''Synthesis, Antifungal and Antioxidant Screening of Some Novel Benzimidazole Derivatives'', Journal of Enzyme Inhibition and Medicinal Chemistry, 22: 696-701, (2007). doi: 10.1080/14756360701228558
20. Kilcigil A. G., Kuş C., Özdamar E. D., Can B., İscan M., ''Synthesis and Antioxidant Capacities of Some New Benzimidazole Derivatives'', Archiv der Pharmazie, 340: 607–611, (2007). doi: 10.1002/ardp.200700088
21. Ateş-Alagöz Z., Kuş C., Çoban T., ''Synthesis and Antioxidant Properties of Novel Benzimidazoles Containing Substituted Indole or 1,1,4,4-Tetramethyl-1,2,3,4-Tetrahydro-Naphthalene Fragments'', Journal of Enzyme Inhibition and Medicinal Chemistry, 20: 325–331, (2005). doi: 10.1080/14756360500131706
22. Sharma R., Bali A., Chaudhari, B. B., ''Synthesis of Methanesulphonamid -Benzimidazole Derivatives as Gastro-Sparing Antiinflammatory Agents with Antioxidant Effect'', Bioorganic & Medicinal Chemistry Letters, 27: 3007–3013, (2017). doi: 10.1016/j.bmcl.2017.05.017
23. Castro A. R., Rivera I. L., Rojas L. C. A., Vazquez G., Rodríguez A. N., ''Synthesis and Preliminary Evaluation of Selected 2-Aryl-5(6)-Nitro-1H-Benzimidazole Derivatives as Potential Anticancer Agents'', Archives of Pharmacal Research, 34: 181-189, (2011). doi: 10.1007/s12272-011-0201-5
24. Demirayak S., Kayagil I., Yurttas L., ''Microwave Supported Synthesis of Some Novel 1,3-Diarylpyrazino-[1,2-A]-Benzimidazole Derivatives and Investigation of Their Anticancer Activities'', European Journal of Medicinal Chemistry, 46: 411-416, (2011). doi: 10.1016/j.ejmech.2010.11.007
25. Nail M. S., Rosario S., Frederic G., Jean-Claude G. B., ''Benzothiazole-and Benzoxazole-Substituted Pyridine-2-Carboxylates as Efficient Sensitizers of Europium Luminescence'', Inorganic Chemistry, 48: 6178–6191, (2009). doi: 10.1021/ic9005136
26. Ma X., Qui X., Jin R., Kang C., Gao L., ''Synthesis and Properties of Fluorescence Poly (Benzoxazole–Imide) s Containing Naphthalene'', High Performance Polymers, 27: 734–741, (2015). doi: 10.1177/0954008314559552
27. Myung G. C., Sang H. L., Yun U. J., Ja M. H., Suk K. C., ''Fluorescence Signaling of BF3 Species byTransformation of an ESIPT Dye to its Difluoroboron Adduct'', Sensors and Actuators B: Chemical, 251: 713–719, (2017). doi: 0.1016/j.snb.2017.05.098
28. Salahuddin M., Mazumder A., Abdullah M. M., ''Synthesis, Characterization and Antimicrobial Activity of 1,3,4-Oxadiazole Bearing 1H-Benzimidazole Derivatives'', Arabian Journal of Chemistry, 10: 503–508, (2017). doi: 10.1016/j.arabjc.2012.10.010
29. Karaali N., ''Synthesis of Some New Benzimidazole Derivatives Containing Chlorine and Investigation of Their Antioxidant and Anti-Urease Activities'', Journal of the Turkish Chemical Society Section A: Chemistry, 5: 971-980, (2018). doi: 10.18596/jotcsa.440202
30. Mochona B., Mazzio E., Gangapurum M., Mateeva N., Redda K. K., ''Synthesis of Some Benzimidazole Derivatives Bearing 1,3,4-Oxadiazole Moiety as Anticancer Agents'', Chemical Science Transactions, 4: 534–540, (2015). doi: 10.7598/cst2015.1029
31. Kapoor A., Dhiman N., ''Anticancer Evaluation of 2-Aryl Substituted Benzimidazole Derivatives Bearing 1,3,4-Oxadiazole Nucleus'', Der Pharmacia Lettre, 8: 149-156, (2016).
32. Youssif G. M., Mohamed Y. A., Salim M. T., Inagakı F., Mukai C., et al., ''Synthesis of Some Benzimidazole Derivatives Endowed with 1,2,3-Triazole as Potential Inhibitors of Hepatitis C Virus'', Acta Pharmaceutica, 66: 219-231, (2016). doi: 10.1515/acph-2016-0014
33. Shingalapur R. V., Hosamani K. M., Keri R. S., Hugar M. H., ''Derivatives of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic and DNA Cleavage Studies'', European Journal of Medicinal Chemistry, 45: 1753–1759, (2010). doi: 10.1016/j.ejmech.2010.01.007
34. Zawawi N. K., Taha M., Ahmat N., Wadood A., Ismail N. H., et al., ''Novel 2,5-Disubtituted-1,3,4-Oxadiazoles with Benzimidazole Backbone: A New Class of B-Glucuronidase Inhibitors and in Silico Studies'', Bioorganic & Medicinal Chemistry, 23: 3119-3125, (2015). doi: 10.1016/j.bmc.2015.04.081
35. Tantray M. A., Khan I., Hamid H., Alam M. S., Dhulap A., et al., ''Synthesis of Benzimidazole-Linked-1,3,4-Oxadiazole Carboxamides as GSK-3b İnhibitors with In Vivo Antidepressant Activity'', Bioorganic Chemistry, 77:393–401, (2018). doi: 10.1016/j.bioorg.2018.01.040
36. Keri R. S., Hiremathad A., Budagumpi S., Nagaraja B. M., ''Comprehensive Review in Current Developments of Benzimidazole-Based Medicinal Chemistry'', Chemical Biology & Drug Design, 86: 19–65, (2015). doi: 10.1111/cbdd.12462
37. Kerimov I., Kilcigil G. A., Can-Eke B., Altanlar N., İşcan M., ''Synthesis, Antifungal and Antioxidant Screening of Some Novel Benzimidazole Derivatives'', Journal of Enzyme Inhibition and Medicinal Chemistry, 22: 696–701, (2007). doi: 10.1080/14756360701228558
38. Kuş C., Kılcıgil G. A., Özbey S., Betu F., Kaynak I., et al., ''Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class'', Bioorganic & Medicinal Chemistry, 16: 4294-4303, (2008). doi: 10.1016/j.bmc.2008.02.077
39. Sandeep N. N., Shreyas S. M., Raju P. K., ''Synthesis of Benzimidazole Derivatives in An Aqueous Media and Reflux Conditions Catalysed by L-Proline at pH-4.2'', International Journal of Research and Analytical Reviews, 6: 485-491, (2019). doi: 10.1729/Journal.21332
40. Heaney H., Ley S. V., ''N-alkylation of indole and pyrroles in dimethyl sulphoxide'', Journal of the Chemical Society Perkin Transactions 1, 4: 499–500, (1973). doi: 10.1039/P19730000499
41. Blois M. S., ''Antioxidant Determinations by the Use of a Stable Free Radical'', Nature, 181: 1199–1200, (1958). doi: 10.1038/1811199a0
42. Burke M. D., Mayer R. T., ''Ethoxyresorufin: direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcholanthrene'', Drug Metabolism and Disposition, 2: 583-588, (1974).
43. Wills E. D., ''Mechanism of lipid peroxide formation in animal tissues'', Biochemical Journal, 99: 667-676 (1966). doi: 10.1042/bj0990667
44. Wills E. D., ''Lipid peroxide formation in microsomes. Relationship of hydroxylation to lipid peroxide formation'', Biochemical Journal, 113: 333-341, (1969). doi: 10.1042/bj1130333

Toplam 44 adet kaynakça vardır.

Ayrıntılar

Birincil Dil	İngilizce
Konular	Mühendislik
Bölüm	Araştırma Makalesi
Yazarlar	Nurhan Gümrükçüoğlu 0000-0002-9669-6318
Yayımlanma Tarihi	1 Aralık 2021
Gönderilme Tarihi	13 Nisan 2020
Yayımlandığı Sayı	Yıl 2021

Kaynak Göster

APA	Gümrükçüoğlu, N. (2021). Synthesis and Antioxidant Properties of New Benzimidazole Derivatives. Politeknik Dergisi, 24(4), 1699-1706. https://doi.org/10.2339/politeknik.718979
AMA	Gümrükçüoğlu N. Synthesis and Antioxidant Properties of New Benzimidazole Derivatives. Politeknik Dergisi. Aralık 2021;24(4):1699-1706. doi:10.2339/politeknik.718979
Chicago	Gümrükçüoğlu, Nurhan. “Synthesis and Antioxidant Properties of New Benzimidazole Derivatives”. Politeknik Dergisi 24, sy. 4 (Aralık 2021): 1699-1706. https://doi.org/10.2339/politeknik.718979.
EndNote	Gümrükçüoğlu N (01 Aralık 2021) Synthesis and Antioxidant Properties of New Benzimidazole Derivatives. Politeknik Dergisi 24 4 1699–1706.
IEEE	N. Gümrükçüoğlu, “Synthesis and Antioxidant Properties of New Benzimidazole Derivatives”, Politeknik Dergisi, c. 24, sy. 4, ss. 1699–1706, 2021, doi: 10.2339/politeknik.718979.
ISNAD	Gümrükçüoğlu, Nurhan. “Synthesis and Antioxidant Properties of New Benzimidazole Derivatives”. Politeknik Dergisi 24/4 (Aralık 2021), 1699-1706. https://doi.org/10.2339/politeknik.718979.
JAMA	Gümrükçüoğlu N. Synthesis and Antioxidant Properties of New Benzimidazole Derivatives. Politeknik Dergisi. 2021;24:1699–1706.
MLA	Gümrükçüoğlu, Nurhan. “Synthesis and Antioxidant Properties of New Benzimidazole Derivatives”. Politeknik Dergisi, c. 24, sy. 4, 2021, ss. 1699-06, doi:10.2339/politeknik.718979.
Vancouver	Gümrükçüoğlu N. Synthesis and Antioxidant Properties of New Benzimidazole Derivatives. Politeknik Dergisi. 2021;24(4):1699-706.

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