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Yeni 3,5-disübstitüe-2-pirazolin türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi

Yıl 2020, Cilt: 22 Sayı: 1, 34 - 47, 10.01.2020
https://doi.org/10.25092/baunfbed.673471

Öz

Bu çalışmada elektronca zengin azot atomu içeren 5 üyeli heterosikliklerden biri olan pirazolin türevi 3 adet yeni bileşik kalkonlardan başlanarak sentezlendi. Pirazolinlerin sahip oldukları biyolojik ve farmakolojik özelliği sebebiyle bu bileşiklerin DPPH radikal süpürme ve fosfomolibdenyum indirgeyici güç (PRAP) aktiviteleri ile tirozinaz ve α-glikozidaz enzim inhibisyon aktiviteleri araştırıldı. Elde edilen veriler doğrultusunda 4 (IC50=16.68 ± 0.19 μM) ve 6 (IC50=22.60 ± 0.83 μM) nolu bileşiklerin standart kojik asitten (IC50=35.41 ± 0.19 μM) daha iyi tirozinaz inhibisyon aktiviteye sahip oldukları belirlendi. Bileşiklerin α-glukozidaz enzim inhibisyon aktiviteleri çok yüksek olmamakla birlikte 4 (IC50=134.24 ± 2.51 μM) nolu bileşik en yüksek aktiviteyi gösterdi. Bileşiklerin antioksidan aktivite değerlerine bakıldığında ise 5 nolu bileşik en yüksek DPPH radikal süpürme (%67.59 ± 0.44) ve fosfomolibdenyum indirgeyici güç (PRAP, Abs= 0.815 ± 0.009) aktivitesini sergiledi. Sonuç olarak bileşik yapılarında farklılık gösteren -NH2 grubunun bağlanma pozisyonu, bileşiklerin biyolojik özelliklerinde belirgin bir farklılığa sebep olmuştur.

Teşekkür

Yapılan çalışmada biyolojik aktivite testlerindeki katkılarından dolayı Arş. Gör. Burak BARUT’a teşekkür ederim.

Kaynakça

  • Aliyazıcıoğlu, R., Akkaya, Ş., Korkmaz, N., Şener, S. Ö., Badem, M., Özgen, U. ve Alpay Karaoğlu, Ş., Onobrychis oxyodonta’nın topraküstü kısmında antioksidan, antimikrobiyal ve tirozinaz inhibitör, Fırat Üniversitesi Sağlık Bilimleri Tıp Dergisi, 31, 1, 25-31, (2017).
  • Qin, H. L., Shang Z. P., Jantan, I., Unsal Tan, O., Hussain M. A., Sher, M., Bukhari ve S. N. Abbas., Molecular docking studies and biological evaluation of chalcone based pyrazolines as tyrosinase inhibitors and potential anticancer agents, RSC Advances, 5, 46330-46338, (2015).
  • Cui, H. X., Duan, F. F., Jia, S. S., Cheng, F. R. ve Yuan, K., Antioxidant and tyrosinase inhibitory activities of seed oils from Torreya grandis Fort. ex Lindl., BioMed Research International, 2018, 10 pages, (2018).
  • Chang, T.S., An updated review of tyrosinase inhibitors, International Journal of Molecular Sciences, 10, 2440-2475, (2009).
  • Turan, E. ve Kulaksızoğlu, M., Tip 2 diyabet tedavisinde güncel yaklaşımlar, Okmeydanı Tıp Dergisi, 31(Ek sayı), 86-94, (2015).
  • Yousefi, R., Alavian-Mehr, M. M., Mokhtari, F., Panahi, F., Mehraban, M.H. ve Khalafi-Nezhad, A., Pyrimidine-fused heterocycle derivatives as a novel class of inhibitors for α-glucosidase, Journal of Enzyme Inhibition and Medicinal Chemistry, 28, 6, 1228-1235, (2013).
  • Elya, B., Basah, K., Mun’im A., Yuliastuti, W., Bangun, A. ve Septiana E. K., Screening of α-glucosidase inhibitory activity from some plants of Apocynaceae, Clusiaceae, Euphorbiaceae, and Rubiaceae, Journal of Biomedicine and Biotechnology, 2012, 6 pages, (2012).
  • Colotta ,V., Catarzi, D., Varano, F., Filacchioni, G. ve Cecchi, L., Synthesis and binding activity of some pyrazolo[1,5-c]quinazolines as tools to verify and optional binding site of a benzodiazepine receptor ligand, Journal of Medicinal Chemistry, 39, 2915-2921, (1996).
  • Patel, M.R., Dodiya, B.L., Ghetiya, R.M., Joshi, K.A., Vekariya, P.B., Bapodara, A.H. ve Joshi, H.S., Synthesis and antimicrobial evaluation of pyrazoline derivatives, International Journal of ChemTech Research, 3, 2, 967-974, (2011).
  • Pinto, D.C.G.A., Silva, A.M.S., Cavaleiro, J.A.S. ve Elguero, J., New bis(chalcones) and their transformation into bis(pyrazoline) and bis(pyrazole) derivatives, European Journal of Organic Chemistry, 4, 747-755, (2003).
  • Rostom, S.A.F, Badr, M.H., Abd El Razik, H.A., Ashour, H.M.A., ve Abdel Wahab, A.E., Synthesis of some pyrazolines and pyrimidines derived from polymethoxy chalcones as anticancer and antimicrobial agents, Archiv der Pharmazie–Chemistry in Life Sciences, 344, 572-587, (2011).
  • Marella, A., Ali, M. R., Alam, M. T., Saha, R., Tanwar, O., Akhter, M., Shaquiquzzaman, M. ve Alam M. M., Pyrazolines: A biological review, Mini Reviews in Medicinal Chemistry, 13, 6, 921-931, (2013).
  • Yusuf, M. ve Jain, P., Synthetic and biological studies of pyrazolines and related heterocyclic compounds, Arabian Journal of Chemistry, 7, 553-596, (2014).
  • Tanwer, N., Kaur, R., Rana, D., Singh, R. ve Singh, K., Synthesis and characterization of pyrazoline derivatives, Journal of Integrated Science & Technology, 3, 2, 39-41, (2015).
  • Bano, S., Alam, M. S., Javed, K., Dudeja, M., Das, A. K. ve Dhulap, A., Synthesis, biological evaluation and molecular docking of some substituted pyrazolines and isoxazolines as potential antimicrobial agents, European Journal of Medicinal Chemistry, 95, 96-103, (2015).
  • Amin, K. M., Eissa, A. A. M., Abou-Seri, S. M., Awadallah, F. M. ve Hassan G. S., Synthesis and biological evaluation of novel coumarinepyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents, European Journal of Medicinal Chemistry, 60, 187-198, (2013).
  • Karabacak, M., Altıntop, M. D., Çiftçi, H. İ., Koga, R., Otsuka, M., Fujita, M., ve Özdemir, A., Synthesis and evaluation of new pyrazoline derivatives as potential anticancer agents, Molecules, 20, 19066-19084, (2015).
  • George, R. F., Fouad, M. A. ve Gomaa, I. E.O., Synthesis and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers, European Journal of Medicinal Chemistry, 112, 48-59, (2016).
  • Viveka, S., Dinesha, Shama, P., Nagaraja, G. K., Ballav, S. ve Kerkar, S., Design and synthesis of some new pyrazolyl-pyrazolines as potential anti-inflammatory, analgesic and antibacterial agents, European Journal of Medicinal Chemistry, 101, 442-451, (2015).
  • He, J., Ma, L.,Wei, Z., Zhu, J., Peng, F., Shao, M., Lei, L.,He, L. ve Tang, M., Synthesis and biological evaluation of novel pyrazoline derivatives as potent anti-inflammatory agents, Bioorganic & Medicinal Chemistry Letters, 25, 2429–2433, (2015).
  • Mallikarjuna Rao, R., Sreeramulu, J., Ravindranath, L. K., Nagaraja Reddy, G., Hanumanthurayudu, K., Nageswara Reddy, G., Jayaraju, A. ve Madhusudhan, P., Synthesis and biological screening of some pyridine and pyrrole derivatives of pyrazolo [3,4-c] pyrazoles, Journal of Chemical and Pharmaceutical Research, 4, 1, 272-278, (2012).
  • Ahmad, P., Woob, H., Jun, K. Y., Kadi, A. A., Abdel-Aziz, H. A., Kwon, Y. ve Motiur Rahman, A. F. M., Design, synthesis, topoisomerase I & II inhibitory activity, antiproliferative activity, and structure–activity relationship study of pyrazoline derivatives: An ATP-competitive human topoisomerase IIα catalytic inhibitör, Bioorganic & Medicinal Chemistry, 24, 1898-1908, (2016).
  • Saeed, A., Mahesar, P. A., Channar, P. A., Abbas, Q., Larik, F. A., Hassan, M., Raza, H. ve Seo, S. Y., Synthesis, molecular docking studies of coumarinyl-pyrazolinyl substituted thiazoles as non-competitive inhibitors of mushroom tyrosinase, Bioorganic Chemistry, 74, 187-196, (2017).
  • Bardalai, D. ve Panneerselvam, P., Pyrazole and pyrazoline derivatives: potential anti-inflammatory and analgesic agents, International Research Journal of Pharmaceutical and Applied Sciences, 2, 3, 1-8, (2012).
  • Blois, M. S., Antioxidant determinations by the use of a stable free radical, Nature, 29, 1199-1200, (1958).
  • Falcioni, G., Fedeli, D., Diano, L., Calzuola, I., Mancinelli, L., Marsili, V. ve Gianfranceschi, G., Antioxidant activity of wheat sprouts extract in vitro: inhibition of DNA oxidative damage, Journal of Food Science, 67, 2918-2922, (2002).
  • Masuda, T., Yamashita, D., Takeda, Y. ve Yonemori, S., Screening for tyrosinase inhibitors among extracts of seashore plants and identification of potent inhibitors from Garcinia subelliptica, Boscience, Biotechnology, Biochemistry, 69, 197-201, (2005).
  • Şöhretoğlu, D., Sari, S., Özel, A. ve Barut, B., α-Glucosidase inhibitory effect of Potentilla astracanica and someisoflavones: Inhibition kinetics and mechanistic insights through in vitro and in silico studies, International Journal of Biological Macromolecules, 105, 1062–1070, (2017).
  • Kahriman, N., Yılmaz İskender, N., Yücel, M., Yaylı, N., Demir, E. ve Demirbağ Z., Microwave assisted synthesis of 1,3’-diazaflavanone/flavones and their alkyl derivatives with antimicrobial activity, Journal of Heterocyclic Chemistry, 49, 1, 71-79, (2012).
  • Kahriman, N., Yaylı, B., Aktaş, A., İskefiyeli, Z., Beriş, F.Ş. ve Yaylı N., Synthesis, antibacterial and antioxidant activities of new 1-Alkyl-4-(1-alkyl-4-oxo-1,4-dihydroquinolin-2-yl)pyridinium bromides, European Journal of Medicinal Chemistry, 69, 348-355, (2013).
  • Kahriman, N., Şenyürek, Z., Serdaroğlu, V., Beriş, F.Ş., Barut, B. ve Yayli, N., Synthesis of novel pyrazolines, their boron–fluorine complexes,and investigation of antibacterial, antioxidant, and enzyme inhibition activities, Archiv Der Pharmazie, 350, 2, 1-12, (2017).
  • Salgın Gökşen, U., Bazı yeni 2-pirazolin türevlerinin sentezi ve monoamin oksidaz (MAO) inhibitör aktiviteleri üzerinde çalışmalar, Doktora Tezi, Hacettepe Üniversitesi, Sağlık Bilimleri Enstitüsü, Ankara, (2015).

Synthesis and biological activity investigation of new 3,5-disubstituted-2-pyrazoline derivatives

Yıl 2020, Cilt: 22 Sayı: 1, 34 - 47, 10.01.2020
https://doi.org/10.25092/baunfbed.673471

Öz

In this study 3 new pyrazolines, one of the electron-rich nitrogen containing heterocyclics, derivative compounds were synthesized starting from chalcones. Due to the biological and pharmacological properties of pyrazolines, DPPH radical scavenging and phosphomolybdenum reducing power (PRAP) activities and tyrosinase and α-glycosidase enzyme inhibition activities of these compounds were investigated . Based on the obtained results, it was determined that compounds 4 (IC50 = 16.68 ± 0.19 μM) and 6 (IC50 = 22.60 ± 0.83 μM) had better tyrosinase inhibitory activities than standard kojic acid (IC50 = 35.41 ± 0.19 μM). Although the α-glucosidase enzyme inhibition activities of the compounds were not very high, compound 4 (IC50 = 134.24 ± 2.51 μM) showed the highest activity. When the antioxidant activity values of the compounds were examined, compound 5 showed the highest DPPH radical scavenging (67.59 ± 0.44%) and phosphomolybdenum reducing power (PRAP, Abs = 0.815 ± 0.009) activities. As a result, the binding position of the -NH2 group, which differed in the compound structures, also caused a significant difference in the biological properties of the compounds..

Kaynakça

  • Aliyazıcıoğlu, R., Akkaya, Ş., Korkmaz, N., Şener, S. Ö., Badem, M., Özgen, U. ve Alpay Karaoğlu, Ş., Onobrychis oxyodonta’nın topraküstü kısmında antioksidan, antimikrobiyal ve tirozinaz inhibitör, Fırat Üniversitesi Sağlık Bilimleri Tıp Dergisi, 31, 1, 25-31, (2017).
  • Qin, H. L., Shang Z. P., Jantan, I., Unsal Tan, O., Hussain M. A., Sher, M., Bukhari ve S. N. Abbas., Molecular docking studies and biological evaluation of chalcone based pyrazolines as tyrosinase inhibitors and potential anticancer agents, RSC Advances, 5, 46330-46338, (2015).
  • Cui, H. X., Duan, F. F., Jia, S. S., Cheng, F. R. ve Yuan, K., Antioxidant and tyrosinase inhibitory activities of seed oils from Torreya grandis Fort. ex Lindl., BioMed Research International, 2018, 10 pages, (2018).
  • Chang, T.S., An updated review of tyrosinase inhibitors, International Journal of Molecular Sciences, 10, 2440-2475, (2009).
  • Turan, E. ve Kulaksızoğlu, M., Tip 2 diyabet tedavisinde güncel yaklaşımlar, Okmeydanı Tıp Dergisi, 31(Ek sayı), 86-94, (2015).
  • Yousefi, R., Alavian-Mehr, M. M., Mokhtari, F., Panahi, F., Mehraban, M.H. ve Khalafi-Nezhad, A., Pyrimidine-fused heterocycle derivatives as a novel class of inhibitors for α-glucosidase, Journal of Enzyme Inhibition and Medicinal Chemistry, 28, 6, 1228-1235, (2013).
  • Elya, B., Basah, K., Mun’im A., Yuliastuti, W., Bangun, A. ve Septiana E. K., Screening of α-glucosidase inhibitory activity from some plants of Apocynaceae, Clusiaceae, Euphorbiaceae, and Rubiaceae, Journal of Biomedicine and Biotechnology, 2012, 6 pages, (2012).
  • Colotta ,V., Catarzi, D., Varano, F., Filacchioni, G. ve Cecchi, L., Synthesis and binding activity of some pyrazolo[1,5-c]quinazolines as tools to verify and optional binding site of a benzodiazepine receptor ligand, Journal of Medicinal Chemistry, 39, 2915-2921, (1996).
  • Patel, M.R., Dodiya, B.L., Ghetiya, R.M., Joshi, K.A., Vekariya, P.B., Bapodara, A.H. ve Joshi, H.S., Synthesis and antimicrobial evaluation of pyrazoline derivatives, International Journal of ChemTech Research, 3, 2, 967-974, (2011).
  • Pinto, D.C.G.A., Silva, A.M.S., Cavaleiro, J.A.S. ve Elguero, J., New bis(chalcones) and their transformation into bis(pyrazoline) and bis(pyrazole) derivatives, European Journal of Organic Chemistry, 4, 747-755, (2003).
  • Rostom, S.A.F, Badr, M.H., Abd El Razik, H.A., Ashour, H.M.A., ve Abdel Wahab, A.E., Synthesis of some pyrazolines and pyrimidines derived from polymethoxy chalcones as anticancer and antimicrobial agents, Archiv der Pharmazie–Chemistry in Life Sciences, 344, 572-587, (2011).
  • Marella, A., Ali, M. R., Alam, M. T., Saha, R., Tanwar, O., Akhter, M., Shaquiquzzaman, M. ve Alam M. M., Pyrazolines: A biological review, Mini Reviews in Medicinal Chemistry, 13, 6, 921-931, (2013).
  • Yusuf, M. ve Jain, P., Synthetic and biological studies of pyrazolines and related heterocyclic compounds, Arabian Journal of Chemistry, 7, 553-596, (2014).
  • Tanwer, N., Kaur, R., Rana, D., Singh, R. ve Singh, K., Synthesis and characterization of pyrazoline derivatives, Journal of Integrated Science & Technology, 3, 2, 39-41, (2015).
  • Bano, S., Alam, M. S., Javed, K., Dudeja, M., Das, A. K. ve Dhulap, A., Synthesis, biological evaluation and molecular docking of some substituted pyrazolines and isoxazolines as potential antimicrobial agents, European Journal of Medicinal Chemistry, 95, 96-103, (2015).
  • Amin, K. M., Eissa, A. A. M., Abou-Seri, S. M., Awadallah, F. M. ve Hassan G. S., Synthesis and biological evaluation of novel coumarinepyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents, European Journal of Medicinal Chemistry, 60, 187-198, (2013).
  • Karabacak, M., Altıntop, M. D., Çiftçi, H. İ., Koga, R., Otsuka, M., Fujita, M., ve Özdemir, A., Synthesis and evaluation of new pyrazoline derivatives as potential anticancer agents, Molecules, 20, 19066-19084, (2015).
  • George, R. F., Fouad, M. A. ve Gomaa, I. E.O., Synthesis and cytotoxic activities of some pyrazoline derivatives bearing phenyl pyridazine core as new apoptosis inducers, European Journal of Medicinal Chemistry, 112, 48-59, (2016).
  • Viveka, S., Dinesha, Shama, P., Nagaraja, G. K., Ballav, S. ve Kerkar, S., Design and synthesis of some new pyrazolyl-pyrazolines as potential anti-inflammatory, analgesic and antibacterial agents, European Journal of Medicinal Chemistry, 101, 442-451, (2015).
  • He, J., Ma, L.,Wei, Z., Zhu, J., Peng, F., Shao, M., Lei, L.,He, L. ve Tang, M., Synthesis and biological evaluation of novel pyrazoline derivatives as potent anti-inflammatory agents, Bioorganic & Medicinal Chemistry Letters, 25, 2429–2433, (2015).
  • Mallikarjuna Rao, R., Sreeramulu, J., Ravindranath, L. K., Nagaraja Reddy, G., Hanumanthurayudu, K., Nageswara Reddy, G., Jayaraju, A. ve Madhusudhan, P., Synthesis and biological screening of some pyridine and pyrrole derivatives of pyrazolo [3,4-c] pyrazoles, Journal of Chemical and Pharmaceutical Research, 4, 1, 272-278, (2012).
  • Ahmad, P., Woob, H., Jun, K. Y., Kadi, A. A., Abdel-Aziz, H. A., Kwon, Y. ve Motiur Rahman, A. F. M., Design, synthesis, topoisomerase I & II inhibitory activity, antiproliferative activity, and structure–activity relationship study of pyrazoline derivatives: An ATP-competitive human topoisomerase IIα catalytic inhibitör, Bioorganic & Medicinal Chemistry, 24, 1898-1908, (2016).
  • Saeed, A., Mahesar, P. A., Channar, P. A., Abbas, Q., Larik, F. A., Hassan, M., Raza, H. ve Seo, S. Y., Synthesis, molecular docking studies of coumarinyl-pyrazolinyl substituted thiazoles as non-competitive inhibitors of mushroom tyrosinase, Bioorganic Chemistry, 74, 187-196, (2017).
  • Bardalai, D. ve Panneerselvam, P., Pyrazole and pyrazoline derivatives: potential anti-inflammatory and analgesic agents, International Research Journal of Pharmaceutical and Applied Sciences, 2, 3, 1-8, (2012).
  • Blois, M. S., Antioxidant determinations by the use of a stable free radical, Nature, 29, 1199-1200, (1958).
  • Falcioni, G., Fedeli, D., Diano, L., Calzuola, I., Mancinelli, L., Marsili, V. ve Gianfranceschi, G., Antioxidant activity of wheat sprouts extract in vitro: inhibition of DNA oxidative damage, Journal of Food Science, 67, 2918-2922, (2002).
  • Masuda, T., Yamashita, D., Takeda, Y. ve Yonemori, S., Screening for tyrosinase inhibitors among extracts of seashore plants and identification of potent inhibitors from Garcinia subelliptica, Boscience, Biotechnology, Biochemistry, 69, 197-201, (2005).
  • Şöhretoğlu, D., Sari, S., Özel, A. ve Barut, B., α-Glucosidase inhibitory effect of Potentilla astracanica and someisoflavones: Inhibition kinetics and mechanistic insights through in vitro and in silico studies, International Journal of Biological Macromolecules, 105, 1062–1070, (2017).
  • Kahriman, N., Yılmaz İskender, N., Yücel, M., Yaylı, N., Demir, E. ve Demirbağ Z., Microwave assisted synthesis of 1,3’-diazaflavanone/flavones and their alkyl derivatives with antimicrobial activity, Journal of Heterocyclic Chemistry, 49, 1, 71-79, (2012).
  • Kahriman, N., Yaylı, B., Aktaş, A., İskefiyeli, Z., Beriş, F.Ş. ve Yaylı N., Synthesis, antibacterial and antioxidant activities of new 1-Alkyl-4-(1-alkyl-4-oxo-1,4-dihydroquinolin-2-yl)pyridinium bromides, European Journal of Medicinal Chemistry, 69, 348-355, (2013).
  • Kahriman, N., Şenyürek, Z., Serdaroğlu, V., Beriş, F.Ş., Barut, B. ve Yayli, N., Synthesis of novel pyrazolines, their boron–fluorine complexes,and investigation of antibacterial, antioxidant, and enzyme inhibition activities, Archiv Der Pharmazie, 350, 2, 1-12, (2017).
  • Salgın Gökşen, U., Bazı yeni 2-pirazolin türevlerinin sentezi ve monoamin oksidaz (MAO) inhibitör aktiviteleri üzerinde çalışmalar, Doktora Tezi, Hacettepe Üniversitesi, Sağlık Bilimleri Enstitüsü, Ankara, (2015).
Toplam 32 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Araştırma Makalesi
Yazarlar

Nuran Kahriman 0000-0001-9729-433X

Yayımlanma Tarihi 10 Ocak 2020
Gönderilme Tarihi 26 Mart 2019
Yayımlandığı Sayı Yıl 2020 Cilt: 22 Sayı: 1

Kaynak Göster

APA Kahriman, N. (2020). Yeni 3,5-disübstitüe-2-pirazolin türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 22(1), 34-47. https://doi.org/10.25092/baunfbed.673471
AMA Kahriman N. Yeni 3,5-disübstitüe-2-pirazolin türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi. BAUN Fen. Bil. Enst. Dergisi. Ocak 2020;22(1):34-47. doi:10.25092/baunfbed.673471
Chicago Kahriman, Nuran. “Yeni 3,5-disübstitüe-2-Pirazolin türevlerinin Sentezi Ve Biyolojik Aktivitelerinin Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 22, sy. 1 (Ocak 2020): 34-47. https://doi.org/10.25092/baunfbed.673471.
EndNote Kahriman N (01 Ocak 2020) Yeni 3,5-disübstitüe-2-pirazolin türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 22 1 34–47.
IEEE N. Kahriman, “Yeni 3,5-disübstitüe-2-pirazolin türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi”, BAUN Fen. Bil. Enst. Dergisi, c. 22, sy. 1, ss. 34–47, 2020, doi: 10.25092/baunfbed.673471.
ISNAD Kahriman, Nuran. “Yeni 3,5-disübstitüe-2-Pirazolin türevlerinin Sentezi Ve Biyolojik Aktivitelerinin Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi 22/1 (Ocak 2020), 34-47. https://doi.org/10.25092/baunfbed.673471.
JAMA Kahriman N. Yeni 3,5-disübstitüe-2-pirazolin türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi. BAUN Fen. Bil. Enst. Dergisi. 2020;22:34–47.
MLA Kahriman, Nuran. “Yeni 3,5-disübstitüe-2-Pirazolin türevlerinin Sentezi Ve Biyolojik Aktivitelerinin Incelenmesi”. Balıkesir Üniversitesi Fen Bilimleri Enstitüsü Dergisi, c. 22, sy. 1, 2020, ss. 34-47, doi:10.25092/baunfbed.673471.
Vancouver Kahriman N. Yeni 3,5-disübstitüe-2-pirazolin türevlerinin sentezi ve biyolojik aktivitelerinin incelenmesi. BAUN Fen. Bil. Enst. Dergisi. 2020;22(1):34-47.