Araştırma Makalesi
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SYNTHESIS OF SOME BENZOXAZOLE-2(3H)-ONE/BENZOTHIAZOLE-2(3H)-ONE DERIVATIVES AND INVESTIGATION OF THEIR EFFECTS AGAINST ALZHEIMER'S DISEASE

Yıl 2024, Cilt: 48 Sayı: 1, 226 - 241, 20.01.2024
https://doi.org/10.33483/jfpau.1387244

Öz

Objective: In this study, 28 new acetamide derivatives bearing benzoxazole/benzothiazole rings were synthesized and their effects against Alzheimer's disease were tested in vitro.
Material and Method: Amine derivatives (5 and 6) used in the synthesis of final compounds were synthesized by the methylation of commercially available 1,3-benzoxazol-2(3H)-one or 1,3-benzothiazol-2(3H)-one rings with dimethyl sulfate followed by nitration with nitric acid and then reduction with tin chloride. In order to synthesize acetamide derivatives, 5 and 6 was first acylated with bromoacetyl bromide to obtain intermediates 7 and 8. Then, these compounds was reacted with appropriate secondary amines to get the title compounds (9a-n and 10a-n). The structure of the synthesized compounds was elucidated by spectroscopic methods, HRMS and elemental analysis. After the cholinesterase inhibitor activities of all title compounds were determined by the modified Ellman method, their antioxidant activities were measured by the DPPH and ORAC method. Finally, the metal chelator properties of the title compounds were determined.
Result and Discussion: New 2-substituted-N-(3-methyl-2-oxo-2,3-dihydro-1,3-benzoxazol/1,3- benzothiazol-6-yl)acetamide derivative compounds were synthesized. Their cholinesterase inhibitory effects and structure activity relationships were determined. Compound 10g (IC50: 52.90 µM) was identified as the most potent acetylcholinesterase (AChE) inhibitor, and also compound 10h (IC50: 51.03 µM) was determined as the most active derivative for the butyrylcholinesterase (BChE). In the ORAC antioxidant activity test, compounds carrying phenylpiperazine derivatives in their side chains were found to show 3-5 times higher antioxidant activity than the reference trolox. Additionally, the metal chelator activity results of the title compounds showed that the majority of them had metal chelator properties.

Kaynakça

  • 1. Alzheimer’s Association (2016). 2016 Alzheimer's disease facts and figures. Alzheimer's & Dementia, 12(4), 459-509. [CrossRef]
  • 2. Frozza, R.L., Lourenco, M.V., De Felice, F.G. (2018). Challenges for Alzheimer's disease therapy: Insights from novel mechanisms beyond memory defects. Frontiers in Neuroscience, 12, 37. [CrossRef]
  • 3. De Ture, M.A., Dickson, D.W. (2019). The neuropathological diagnosis of Alzheimer’s disease. Molecular Neurodegeneration, 14(1), 32. [CrossRef]
  • 4. Maria Cecilia Rodrigues, S., Flavia Pereira Dias, V., Marcella Soares, M., Matheus de Freitas, S., Mariana Maximo, R., Patricia Mattos da, R., Maísa Rosa, C., Marcelo Henrique dos, S., Marisi Gomes, S.Claudio, V. (2014). Donepezil: an important prototype to the design of new drug candidates for alzheimer’s disease. Mini-Reviews in Medicinal Chemistry, 14(1), 2-19. [CrossRef]
  • 5. Zemek, F., Drtinova, L., Nepovimova, E., Sepsova, V., Korabecny, J., Klimes, J., Kuca, K. (2014). Outcomes of Alzheimer's disease therapy with acetylcholinesterase inhibitors and memantine. Expert Opinion on Drug Safety, 13(6), 759-774.
  • 6. Sang, Z., Song, Q., Cao, Z., Deng, Y., Tan, Z., Zhang, L. (2021). Design, synthesis and evaluation of novel dimethylamino chalcone-O-alkylamines derivatives as potential multifunctional agents against Alzheimer’s disease. European Journal of Medicinal Chemistry, 216, 113310. [CrossRef]
  • 7. Wang, M., Liu, T., Chen, S., Wu, M., Han, J., Li, Z. (2021). Design and synthesis of 3-(4-pyridyl)-5-(4-sulfamido-phenyl)-1,2,4-oxadiazole derivatives as novel GSK-3β inhibitors and evaluation of their potential as multifunctional anti-Alzheimer agents. European Journal of Medicinal Chemistry, 209, 112874. [CrossRef]
  • 8. Kandimalla, R., Reddy, P.H. (2017). Therapeutics of neurotransmitters in Alzheimer’s disease. Journal of Alzheimer's Disease, 57, 1049-1069.
  • 9. Agatonovic-Kustrin, S., Kettle, C., Morton, D.W. (2018). A molecular approach in drug development for Alzheimer’s disease. Biomedicine and Pharmacotherapy, 106, 553-565. [CrossRef]
  • 10. Bajda, M., Więckowska, A., Hebda, M., Guzior, N., Sotriffer, C.A., Malawska, B. (2013). Structure-based search for new inhibitors of cholinesterases. International Journal of Molecular Sciences, 14(3), 5608-5632. [CrossRef]
  • 11. Fang, L., Pan, Y., Muzyka, J.L., Zhan, C.G. (2011). Active site gating and substrate specificity of butyrylcholinesterase and acetylcholinesterase: insights from molecular dynamics simulations. The Journal of Physical Chemistry B, 115(27), 8797-8805. [CrossRef]
  • 12. Bortolami, M., Pandolfi, F., De Vita, D., Carafa, C., Messore, A., Di Santo, R., Feroci, M., Costi, R., Chiarotto, I., Bagetta, D., Alcaro, S., Colone, M., Stringaro, A.Scipione, L. (2020). New deferiprone derivatives as multi-functional cholinesterase inhibitors: Design, synthesis and in vitro evaluation. European Journal of Medicinal Chemistry, 198, 112350. [CrossRef]
  • 13. Zhang, Z., Guo, J., Cheng, M., Zhou, W., Wan, Y., Wang, R., Fang, Y., Jin, Y., Liu, J., Xie, S.S. (2021). Design, synthesis, and biological evaluation of novel xanthone-alkylbenzylamine hybrids as multifunctional agents for the treatment of Alzheimer’s disease. European Journal of Medicinal Chemistry, 213, 113154. [CrossRef]
  • 14. Singh, A., Kukreti, R., Saso, L., Kukreti, S. (2019). Oxidative stress: A key modulator in neurodegenerative diseases. Molecules, 24(8), 1583. [CrossRef]
  • 15. Tariq, S., Kamboj, P., Amir, M. (2019). Therapeutic advancement of benzothiazole derivatives in the last decennial period. Archiv der Pharmazie, 352(1), 1800170. [CrossRef]
  • 16. Doğruer, D.S., Ünlü, S., Şahin, M.F., Yeşilada, E. (1998). Anti-nociceptive and anti-inflammatory activity of some (2-benzoxazolone-3-yl and 2-benzothiazolone-3-yl) acetic acid derivatives. Il Farmaco, 53(1), 80-84. [CrossRef]
  • 17. Doğruer, D.S., Ünlü, S., Yeşilada, E., Şahin, M.F. (1997). N-(2-pyridinyl)-2-[2(3H)-benzazolone-3-yl]acetamides: synthesis, antinociceptive and anti-inflammatory activity. Farmaco, 52(12), 745-750.
  • 18. Önkol, T., Dogruer, D.S., Ito, S.Sahin, M.F. (2000). Synthesis and antinociceptive activity of (5-chloro-2-benzothiazolinon-3-yl)acetamide derivatives. Archiv der Pharmazie, 333(10), 337-340. [CrossRef]
  • 19. Gülkok, Y., Biçer, T., Onurdağ, F.K., Özgen, S., Şahin, M.F., Doğruer, D.S. (2012). Synthesis of some new urea and thiourea derivatives and evaluation of their antimicrobial activities. Turkish Journal of Chemistry, 36(2), 279-291. [CrossRef]
  • 20. Ünal, A.S., Onurdağ, F.K., Özgen, S., Doğruer, D., Önkol, T. (2015). Studies on the synthesis of 3-methyl-6-(substituted-urea/-thiourea)-2(3H)-benzothiazolone derivatives and antimicrobial activities. Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry, 54(2), 253-259.
  • 21. Çakir, B., Ulucay, A., Dogruer, D.S., Isimer, A., Sahin, M.F. (1999). Synthesis and antinociceptive activity of some 3-substituted benzothiazolone derivatives. Il Farmaco, 54(11), 846-851.
  • 22. Erdogan, M., Kilic, B., Sagkan, R.I., Aksakal, F., Ercetin, T., Gulcan, H.O., Dogruer, D.S. (2021). Design, synthesis and biological evaluation of new benzoxazolone/benzothiazolone derivatives as multi-target agents against Alzheimer’s disease. European Journal of Medicinal Chemistry, 212(113124). [CrossRef]
  • 23. Kılıç, B., Gülcan, H.O., Aksakal, F., Erçetin, T., Oruklu, N., Ümit Bagriacik, E., Doğruer, D.S. (2018). Design and synthesis of some new carboxamide and propanamide derivatives bearing phenylpyridazine as a core ring and the investigation of their inhibitory potential on in-vitro acetylcholinesterase and butyrylcholinesterase. Bioorganic Chemistry, 79, 235-249. [CrossRef]
  • 24. Kılıç, B., Erdoğan, M., Gülcan, H.O., Aksakal, F., Oruklu, N., Bağrıaçık, E.U., Doğruer, D.S. (2019). Design, synthesis and investigation of new diphenyl substituted pyridazinone derivatives as both cholinesterase and aβ-aggregation inhibitors. Medicinal Chemistry, 15(1), 59-76. [CrossRef]
  • 25. Kilic, B., Bardakkaya, M., Ilıkcı Sagkan, R., Aksakal, F., Shakila, S.Dogruer, D.S. (2023). New thiourea and benzamide derivatives of 2-aminothiazole as multi-target agents against Alzheimer's disease: Design, synthesis, and biological evaluation. Bioorganic Chemistry, 131, 106322. [CrossRef]
  • 26. Bardakkaya, M., Kilic, B., Sagkan, R.I., Aksakal, F., Shakila, S., Dogruer, D.S. (2023). Synthesis and evaluation of multitarget new 2-aminothiazole derivatives as potential anti-Alzheimer's agents. Archiv der Pharmazie, 356(8), 2300054. [CrossRef]
  • 27. Mao, F., Huang, L., Luo, Z., Liu, A., Lu, C., Xie, Z., Li, X. (2012). O-Hydroxyl- or o-amino benzylamine-tacrine hybrids: Multifunctional biometals chelators, antioxidants, and inhibitors of cholinesterase activity and amyloid-β aggregation. Bioorganic and Medicinal Chemistry, 20(19), 5884-5892. [CrossRef]

BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ

Yıl 2024, Cilt: 48 Sayı: 1, 226 - 241, 20.01.2024
https://doi.org/10.33483/jfpau.1387244

Öz

Amaç: Bu çalışmada benzoksazolon/benzotiyazolon halkası taşıyan asetamit türevi 28 yeni bileşik sentez edilmiş ve Alzheimer hastalığına karşı etkileri in vitro olarak test edilmiştir.
Gereç ve Yöntem: Sonuç bileşiklerin sentezinde kullanılan amin türevleri (5 ve 6), öncelikle ticari olarak mevcut 1,3-benzoksazol-2(3H)-on ve 1,3-benzotiyazol-2(3H)-on halkalarının metillenmesi, nitrik asit ile nitrolanması ve ardından kalay klorürle indirgenmesi ile sentez edilmiştir. Daha sonra, amin türevi 5 ve 6’nın bromoasetil bromür ile açilasyonundan hazırlanan ara ürünlerin (7 ve 8) uygun amin türevleri ile tepkimesinden sonuç bileşikler (9a-n ve 10a-n) elde edilmiştir. Sentezlenen bileşiklerin kimyasal yapıları spektroskopik yöntemler, HRMS ve elementel analiz ile aydınlatılmıştır. Tüm sonuç bileşiklerin modifiye Ellman yöntemiyle kolinesteraz inhibitör aktiviteleri belirlendikten sonra DPPH ve ORAC yöntemiyle antioksidan aktiviteleri ölçülmüştür. Son olarak sonuç bileşiklerin metal şelatör özellikleri tayin edilmiştir.
Sonuç ve Tartışma: Yeni 2-sübstitüe-N-(3-metil-2-okso-2,3-dihidro-1,3-benzoksazol/1,3-benzotiyazol-6-il)asetamit türevi bileşikler sentez edilmiştir. Kolinesteraz inhibitör etkileri ve yapı aktivite ilişkileri belirlenmiştir. Asetilkolinesteraz (AKE) inhibisyonu için bileşik 10g’nin (IC50: 52.90 µM), butirilkolinesteraz BKE inhibisyonu için bileşik 10h’nin (IC50: 51.03 µM ) en yüksek aktiviteye sahip olduğu bulunmuştur. ORAC testi ile yapılan antioksidan aktivite tayininde ise yan zincirinde fenilpiperazin türevleri taşıyan bileşiklerin referans trolokstan daha yüksek antioksidan aktivite gösterdikleri bulunmuştur. Ayrıca sonuç bileşiklerin metal şelatör etkileri incelendiğinde büyük çoğunluğunun metal şelatör özellik taşıdığı belirlenmiştir.

Kaynakça

  • 1. Alzheimer’s Association (2016). 2016 Alzheimer's disease facts and figures. Alzheimer's & Dementia, 12(4), 459-509. [CrossRef]
  • 2. Frozza, R.L., Lourenco, M.V., De Felice, F.G. (2018). Challenges for Alzheimer's disease therapy: Insights from novel mechanisms beyond memory defects. Frontiers in Neuroscience, 12, 37. [CrossRef]
  • 3. De Ture, M.A., Dickson, D.W. (2019). The neuropathological diagnosis of Alzheimer’s disease. Molecular Neurodegeneration, 14(1), 32. [CrossRef]
  • 4. Maria Cecilia Rodrigues, S., Flavia Pereira Dias, V., Marcella Soares, M., Matheus de Freitas, S., Mariana Maximo, R., Patricia Mattos da, R., Maísa Rosa, C., Marcelo Henrique dos, S., Marisi Gomes, S.Claudio, V. (2014). Donepezil: an important prototype to the design of new drug candidates for alzheimer’s disease. Mini-Reviews in Medicinal Chemistry, 14(1), 2-19. [CrossRef]
  • 5. Zemek, F., Drtinova, L., Nepovimova, E., Sepsova, V., Korabecny, J., Klimes, J., Kuca, K. (2014). Outcomes of Alzheimer's disease therapy with acetylcholinesterase inhibitors and memantine. Expert Opinion on Drug Safety, 13(6), 759-774.
  • 6. Sang, Z., Song, Q., Cao, Z., Deng, Y., Tan, Z., Zhang, L. (2021). Design, synthesis and evaluation of novel dimethylamino chalcone-O-alkylamines derivatives as potential multifunctional agents against Alzheimer’s disease. European Journal of Medicinal Chemistry, 216, 113310. [CrossRef]
  • 7. Wang, M., Liu, T., Chen, S., Wu, M., Han, J., Li, Z. (2021). Design and synthesis of 3-(4-pyridyl)-5-(4-sulfamido-phenyl)-1,2,4-oxadiazole derivatives as novel GSK-3β inhibitors and evaluation of their potential as multifunctional anti-Alzheimer agents. European Journal of Medicinal Chemistry, 209, 112874. [CrossRef]
  • 8. Kandimalla, R., Reddy, P.H. (2017). Therapeutics of neurotransmitters in Alzheimer’s disease. Journal of Alzheimer's Disease, 57, 1049-1069.
  • 9. Agatonovic-Kustrin, S., Kettle, C., Morton, D.W. (2018). A molecular approach in drug development for Alzheimer’s disease. Biomedicine and Pharmacotherapy, 106, 553-565. [CrossRef]
  • 10. Bajda, M., Więckowska, A., Hebda, M., Guzior, N., Sotriffer, C.A., Malawska, B. (2013). Structure-based search for new inhibitors of cholinesterases. International Journal of Molecular Sciences, 14(3), 5608-5632. [CrossRef]
  • 11. Fang, L., Pan, Y., Muzyka, J.L., Zhan, C.G. (2011). Active site gating and substrate specificity of butyrylcholinesterase and acetylcholinesterase: insights from molecular dynamics simulations. The Journal of Physical Chemistry B, 115(27), 8797-8805. [CrossRef]
  • 12. Bortolami, M., Pandolfi, F., De Vita, D., Carafa, C., Messore, A., Di Santo, R., Feroci, M., Costi, R., Chiarotto, I., Bagetta, D., Alcaro, S., Colone, M., Stringaro, A.Scipione, L. (2020). New deferiprone derivatives as multi-functional cholinesterase inhibitors: Design, synthesis and in vitro evaluation. European Journal of Medicinal Chemistry, 198, 112350. [CrossRef]
  • 13. Zhang, Z., Guo, J., Cheng, M., Zhou, W., Wan, Y., Wang, R., Fang, Y., Jin, Y., Liu, J., Xie, S.S. (2021). Design, synthesis, and biological evaluation of novel xanthone-alkylbenzylamine hybrids as multifunctional agents for the treatment of Alzheimer’s disease. European Journal of Medicinal Chemistry, 213, 113154. [CrossRef]
  • 14. Singh, A., Kukreti, R., Saso, L., Kukreti, S. (2019). Oxidative stress: A key modulator in neurodegenerative diseases. Molecules, 24(8), 1583. [CrossRef]
  • 15. Tariq, S., Kamboj, P., Amir, M. (2019). Therapeutic advancement of benzothiazole derivatives in the last decennial period. Archiv der Pharmazie, 352(1), 1800170. [CrossRef]
  • 16. Doğruer, D.S., Ünlü, S., Şahin, M.F., Yeşilada, E. (1998). Anti-nociceptive and anti-inflammatory activity of some (2-benzoxazolone-3-yl and 2-benzothiazolone-3-yl) acetic acid derivatives. Il Farmaco, 53(1), 80-84. [CrossRef]
  • 17. Doğruer, D.S., Ünlü, S., Yeşilada, E., Şahin, M.F. (1997). N-(2-pyridinyl)-2-[2(3H)-benzazolone-3-yl]acetamides: synthesis, antinociceptive and anti-inflammatory activity. Farmaco, 52(12), 745-750.
  • 18. Önkol, T., Dogruer, D.S., Ito, S.Sahin, M.F. (2000). Synthesis and antinociceptive activity of (5-chloro-2-benzothiazolinon-3-yl)acetamide derivatives. Archiv der Pharmazie, 333(10), 337-340. [CrossRef]
  • 19. Gülkok, Y., Biçer, T., Onurdağ, F.K., Özgen, S., Şahin, M.F., Doğruer, D.S. (2012). Synthesis of some new urea and thiourea derivatives and evaluation of their antimicrobial activities. Turkish Journal of Chemistry, 36(2), 279-291. [CrossRef]
  • 20. Ünal, A.S., Onurdağ, F.K., Özgen, S., Doğruer, D., Önkol, T. (2015). Studies on the synthesis of 3-methyl-6-(substituted-urea/-thiourea)-2(3H)-benzothiazolone derivatives and antimicrobial activities. Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry, 54(2), 253-259.
  • 21. Çakir, B., Ulucay, A., Dogruer, D.S., Isimer, A., Sahin, M.F. (1999). Synthesis and antinociceptive activity of some 3-substituted benzothiazolone derivatives. Il Farmaco, 54(11), 846-851.
  • 22. Erdogan, M., Kilic, B., Sagkan, R.I., Aksakal, F., Ercetin, T., Gulcan, H.O., Dogruer, D.S. (2021). Design, synthesis and biological evaluation of new benzoxazolone/benzothiazolone derivatives as multi-target agents against Alzheimer’s disease. European Journal of Medicinal Chemistry, 212(113124). [CrossRef]
  • 23. Kılıç, B., Gülcan, H.O., Aksakal, F., Erçetin, T., Oruklu, N., Ümit Bagriacik, E., Doğruer, D.S. (2018). Design and synthesis of some new carboxamide and propanamide derivatives bearing phenylpyridazine as a core ring and the investigation of their inhibitory potential on in-vitro acetylcholinesterase and butyrylcholinesterase. Bioorganic Chemistry, 79, 235-249. [CrossRef]
  • 24. Kılıç, B., Erdoğan, M., Gülcan, H.O., Aksakal, F., Oruklu, N., Bağrıaçık, E.U., Doğruer, D.S. (2019). Design, synthesis and investigation of new diphenyl substituted pyridazinone derivatives as both cholinesterase and aβ-aggregation inhibitors. Medicinal Chemistry, 15(1), 59-76. [CrossRef]
  • 25. Kilic, B., Bardakkaya, M., Ilıkcı Sagkan, R., Aksakal, F., Shakila, S.Dogruer, D.S. (2023). New thiourea and benzamide derivatives of 2-aminothiazole as multi-target agents against Alzheimer's disease: Design, synthesis, and biological evaluation. Bioorganic Chemistry, 131, 106322. [CrossRef]
  • 26. Bardakkaya, M., Kilic, B., Sagkan, R.I., Aksakal, F., Shakila, S., Dogruer, D.S. (2023). Synthesis and evaluation of multitarget new 2-aminothiazole derivatives as potential anti-Alzheimer's agents. Archiv der Pharmazie, 356(8), 2300054. [CrossRef]
  • 27. Mao, F., Huang, L., Luo, Z., Liu, A., Lu, C., Xie, Z., Li, X. (2012). O-Hydroxyl- or o-amino benzylamine-tacrine hybrids: Multifunctional biometals chelators, antioxidants, and inhibitors of cholinesterase activity and amyloid-β aggregation. Bioorganic and Medicinal Chemistry, 20(19), 5884-5892. [CrossRef]

Ayrıntılar

Birincil Dil Türkçe
Konular Farmasotik Kimya
Bölüm Araştırma Makalesi
Yazarlar

Merve BARDAKKAYA 0000-0002-5221-8402

Burcu KILIÇ 0000-0001-8737-829X

Deniz DOĞRUER 0000-0002-8221-5579

Proje Numarası TÜBİTAK 115S192
Erken Görünüm Tarihi 7 Ocak 2024
Yayımlanma Tarihi 20 Ocak 2024
Gönderilme Tarihi 7 Kasım 2023
Kabul Tarihi 22 Aralık 2023
Yayımlandığı Sayı Yıl 2024 Cilt: 48 Sayı: 1

Kaynak Göster

APA BARDAKKAYA, M., KILIÇ, B., & DOĞRUER, D. (2024). BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ. Journal of Faculty of Pharmacy of Ankara University, 48(1), 226-241. https://doi.org/10.33483/jfpau.1387244
AMA BARDAKKAYA M, KILIÇ B, DOĞRUER D. BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ. Ankara Ecz. Fak. Derg. Ocak 2024;48(1):226-241. doi:10.33483/jfpau.1387244
Chicago BARDAKKAYA, Merve, Burcu KILIÇ, ve Deniz DOĞRUER. “BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ”. Journal of Faculty of Pharmacy of Ankara University 48, sy. 1 (Ocak 2024): 226-41. https://doi.org/10.33483/jfpau.1387244.
EndNote BARDAKKAYA M, KILIÇ B, DOĞRUER D (01 Ocak 2024) BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ. Journal of Faculty of Pharmacy of Ankara University 48 1 226–241.
IEEE M. BARDAKKAYA, B. KILIÇ, ve D. DOĞRUER, “BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ”, Ankara Ecz. Fak. Derg., c. 48, sy. 1, ss. 226–241, 2024, doi: 10.33483/jfpau.1387244.
ISNAD BARDAKKAYA, Merve vd. “BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ”. Journal of Faculty of Pharmacy of Ankara University 48/1 (Ocak 2024), 226-241. https://doi.org/10.33483/jfpau.1387244.
JAMA BARDAKKAYA M, KILIÇ B, DOĞRUER D. BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ. Ankara Ecz. Fak. Derg. 2024;48:226–241.
MLA BARDAKKAYA, Merve vd. “BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ”. Journal of Faculty of Pharmacy of Ankara University, c. 48, sy. 1, 2024, ss. 226-41, doi:10.33483/jfpau.1387244.
Vancouver BARDAKKAYA M, KILIÇ B, DOĞRUER D. BAZI BENZOKSAZOL-2(3H)-ON/BENZOTİYAZOL-2(3H)-ON TÜREVLERİNİN SENTEZİ VE ALZHEİMER HASTALIĞINA KARŞI ETKİLERİNİN İNCELENMESİ. Ankara Ecz. Fak. Derg. 2024;48(1):226-41.

Kapsam ve Amaç

Ankara Üniversitesi Eczacılık Fakültesi Dergisi, açık erişim, hakemli bir dergi olup Türkçe veya İngilizce olarak farmasötik bilimler alanındaki önemli gelişmeleri içeren orijinal araştırmalar, derlemeler ve kısa bildiriler için uluslararası bir yayım ortamıdır. Bilimsel toplantılarda sunulan bildiriler supleman özel sayısı olarak dergide yayımlanabilir. Ayrıca, tüm farmasötik alandaki gelecek ve önceki ulusal ve uluslararası bilimsel toplantılar ile sosyal aktiviteleri içerir.