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α-Siyanokalkon Bileşiklerinin Sentezi, Karakterizasyonu ve Antibakteriyel, Antifungal ve Antioksidan Aktivitelerinin Belirlenmesi

Year 2025, Volume: 15 Issue: 1, 1 - 16, 01.07.2025

Hakan Aslan , Cumhur Avşar

https://doi.org/10.37094/adyujsci.1584171

Abstract

Bu çalışmada, 3-(heteroaril)-3-oksopropannitriller ile çeşitli aromatik/heteroaromatik aldehitlerin L-prolin aracılığında Knoevenagel kondensasyon reaksiyonları gerçekleştirildi. Bu reaksiyonlarda orta-iyi verimlerde α-siyanokalkon bileşikleri elde edildi. Bileşiklerin yapıları spektroskopik yöntemler kullanılarak aydınlatıldı. Tüm ürünlerin antibakteriyel ve antifungal aktiviteleri hem kuyu- difüzyon yöntemi hem de minimum inhibisyon konsantrasyonu (MIC) yöntemiyle belirlendi. Piridin-3-il grubunu içeren bileşik 1c, hem Gram (+) hem de Gram (-) bakteri ve mantarlara karşı etki göstererek geniş spektrumlu özellikler sergiledi. Bileşiklerin antioksidan aktiviteleri DPPH radikal temizleme yöntemi ile test edildi ve antioksidan aktivite sonuçlarına göre en etkili bileşiğin 1c olduğu bulundu. 1b ve 1d bileşiklerinin de orta düzeyde antioksidan aktiviteye sahip olduğunu söylemek mümkündür.

Keywords

α-Siyanokalkon Knoevenagel kondensasyonu Antimikrobiyal aktivite Antioksidan aktivite

Supporting Institution

This work was supported by the Sinop University Scientific Research Projects Coordination Unit under Grant Number FEF-1901-21-001.

Project Number

FEF-1901-21-001

Thanks

we would like to thank to Sinop University for its financial support.

References

  • Sahu, K.N., Balbhadra, S.S., Choudhary, J., & Kohli, D., Exploring pharmacological significance of chalcone scaffold: a review, Current Medicinal Chemistry, 19(2), 209-225, 2012.
  • Rammohan, A., Reddy, J.S., Sravya, G., Rao, C.N., & Zyryanov, G.V., Chalcone synthesis, properties and medicinal applications:a review, Environmental Chemistry Letters, 18, 433-458, 2020.
  • Nayak, Y.N., Gaonkar, S.L., & Sabu, M., Chalcones:Versatile intermediates in heterocyclic synthesis, Journal of Heterocyclic Chemistry, 60(8), 1301-1325, 2023.
  • Khider, A.K., In vivo Antimicrobial Activity of 1 (4-(4-chlorobenzyloxy) phenyl)-3-(4-methyl Phenyl)-2-propen-1-ones (Chalcone 2) Against klebsiella pneumoniae Isolated from Pneumonia Patients, British Journal of Pharmacology and Toxicology, 2(2), 92-96, 2011.
  • Asiri, A.M., & Khan, S.A., Synthesis and anti-bacterial activities of a bis-chalcone derived from thiophene and its bis-cyclized products, Molecules, 16(1), 523-531, 2011.
  • Edwards, M.L., Stemerick, D.M., & Sunkara, P.S., Chalcones: a new class of antimitotic agents, Journal of Medicinal Chemistry, 33(7), 1948-1954, 1990.
  • Mohamed, M.F., & Abuo-Rahma, G.E.D.A., Molecular targets and anticancer activity of quinoline–chalcone hybrids: Literature review, RSC advances, 10(52), 31139-31155, 2020.
  • Ouyang, Y., Li, J., Chen, X., Fu, X., Sun, S., & Wu, Q., Chalcone derivatives: role in anticancer therapy, Biomolecules, 11(6), 894, 2021.
  • Pereira, R., Silva, A.M., Ribeiro, D., Silva, V.L., & Fernandes, E., Bis-chalcones: A review of synthetic methodologies and anti-inflammatory effects, European Journal of Medicinal Chemistry, 252, 115280, 2023.
  • Siddiqa, A., Tajammal, A., Irfan, A., Azam, M., Munawar, M.A., Hardy, R.S., et al., Synthesis, molecular docking, bio-evaluation and quantitative structure activity relationship of new chalcone derivatives as antioxidants, Journal of Molecular Structure, 1277, 134814, 202.
  • Yamamoto, T., Yoshimura, M., Yamaguchi, F., Kouchi, T., Tsuji, R., Saito, M., et al., Anti-allergic activity of naringenin chalcone from a tomato skin extract, Bioscience, Biotechnology, and Biochemistry, 68(8), 1706-1711, 2004.
  • Mahapatra, D.K., Asati, V., & Bharti, S.K., Chalcones and their therapeutic targets for the management of diabetes: structural and pharmacological perspectives, European journal of Medicinal Chemistry, 92, 839-865, 2015.
  • Kumar, H., Devaraji, V., Joshi, R., Jadhao, M., Ahirkar, P., Prasath, R., et al., Antihypertensive activity of a quinoline appended chalcone derivative and its site specific binding interaction with a relevant target carrier protein, RSC Advances, 5(80), 65496-65513, 2015.
  • Aslan, H., Yetişsin, F., Korkmaz, A., Bursal, E., Design, Synthesis, Characterization, Enzyme Inhibition, Molecular Docking, and Pharmacological Evaluation of New Chalcone‐Sulfonate Derivatives Bearing Thiophene, ChemistrySelect, 9(14), e202400053, 2024.
  • Korkmaz, A., Design, synthesis, characterization, molecular docking studies, molecular properties, toxicity, and bioactivity score prediction evaluation of novel chalcone-sulfonate hybrid derivatives, Journal of Molecular Structure, 1286, 135597, 2023.
  • Singh, G., Arora, A., Kalra, P., Maurya, I.K., Ruizc, C.E., Estebanc, M.A., et al., A strategic approach to the synthesis of ferrocene appended chalcone linked triazole allied organosilatranes: Antibacterial, antifungal, antiparasitic and antioxidant studies, Bioorganic & Medicinal Chemistry, 27(1), 188-195, 2019.
  • Guantai, E.M., Ncokazi, K., Egan, T.J., Gut, J., Rosenthal, P.J., Bhampidipati, R., et al., Enone–and chalcone–chloroquinoline hybrid analogues: in silico guided design, synthesis, antiplasmodial activity, in vitro metabolism, and mechanistic studies, Journal of Medicinal Chemistry, 54(10), 3637-3649, 2011.
  • Al‐Rifai, N.M., & Mubarak, M.S., α‐Substituted Chalcones:A Key Review, ChemistrySelect, 6(46), 13224-13252, 2021.
  • Kumar, D., Kumar, N.M., Tantak, M.P., Ogura, M., Kusaka, E., & Ito, T., Synthesis and identification of α-cyano bis (indolyl) chalcones as novel anticancer agents, Bioorganic & Medicinal Chemistry Letters, 24(22), 5170-5174, 2014.
  • Fahim, A.M., & Farag, A.M. Synthesis, antimicrobial evaluation, molecular docking and theoretical calculations of novel pyrazolo [1,5-a] pyrimidine derivatives, Journal of Molecular Structure, 1199, 127025, 2020.
  • Yilmaz, M., Uzunalioğlu, N., Yakut, M., & Pekel, A.T., Oxidative cyclisation of 3-oxopropanenitriles mediated manganese (III) acetate with 2-thienyl substituted alkenes, Turkish Journal of Chemistry, 32(4), 411-422, 2008.
  • Amancha, P.K., Lai, Y.C., Chen, I.C., Liu, H.J., & Zhu, J.L., Diels–Alder reactions of acyclic α-cyano α, β-alkenones: a new approach to highly substituted cyclohexene system, Tetrahedron, 66(4), 871-877, 2010.
  • Stagos, D., Soulitsiotis, N., Tsadila, C., Papaeconomou, S., Arvanitis, C., Ntontos, A., et al., Antibacterial and antioxidant activity of different types of honey derived from Mount Olympus in Greece, International Journal of Molecular Medicine, 42(2), 726-734, 2018.
  • Mama, M., Teshome, T., & Detamo, J., Antibacterial Activity of Honey against Methicillin-Resistant Staphylococcus aureus: A Laboratory-Based Experimental Study, International Journal of Microbiology, 2019, 7686130, 2019.
  • Blois, M.S., Antioxidant determinations by the use of a stable free radical, Nature, 181(4617), 1199-1200, 1958.
  • Kumar, L.S., Prasad, K.S., & Revanasiddappa, H.D., Synthesis, characterization, antioxidant, antimicrobial, DNA binding and cleavage studies of mononuclear Cu (II) and Co (II) complexes of 3-hydroxy-N'-(2-hydroxybenzylidene)-2-naphthohydrazide, European Journal of Chemistry, 2(3), 394-403, 2011.
  • Ma, L., Yuan, L., Xu, C., Li, G., Tao, M., & Zhang, W., An efficient synthesis of 2-aminothiophenes via the Gewald reaction catalyzed by an N-methylpiperazine-functionalized polyacrylonitrile fiber, Synthesis, 45(01), 45-52, 2013.
  • El-Shenawy, A.I., Synthesis and in vitro antibacterial evaluation of some novel annulated quinazolinone derivatives, Russian Journal of General Chemistry, 88, 1712-1719, 2018.
  • Mohamed, M.F., Ibrahim, N.S., Saddiq, A.A., & Abdelhamid, I.A., Novel 3-(pyrazol-4-yl)-2-(1 H-indole-3-carbonyl) acrylonitrile derivatives induce intrinsic and extrinsic apoptotic death mediated P53 in HCT116 colon carcinoma, Scientific Reports, 13(1), 22486, 2023.
  • Bhale, P.S., Shringare, S.N., Khade, A.B., Chavan, H.V., Synthesis, Characterization and Biological Evaluation of Indole-Pyrazole Amalgamated α-Cyano Substituted Chalcones, Anti-Cancer Agents in Medicinal Chemistry, 21(16), 2216-2223, 2021.
  • Bhale, P.S., Chavan, H.V., Endait, R.S., Kadam, A.T., Bopalkar, R.J., & Gaikwad, M.S., Synthesis and Biological Evaluation of Indolyl Bis-chalcones as Anti-Breast Cancer and Antioxidant Agents, Croatica Chemica Acta, 94(1), 35-41, 2021.
  • Zlotnikov, I.D., Krylov, S.S., Belogurova, N.G., Blinnikov, A.N., Kalugin, V.E., & Kudryashova, E.V., New Derivatives of Chalcones, Chromens and Stilbenoids, Complexed with Methyl-β-Cyclodextrin, Show Antioxidant Properties and Antibacterial Synergism with Antibiotics, Biophysica, 4(4), 667-694, 2024.
  • Sallam, H.A., Elgubbi, A.S., & El-Helw, E.A.E., Synthesis and antioxidant screening of new 2-cyano-3-(1,3-diphenyl-1H-pyrazol-4-yl)acryloyl amide derivatives and some pyrazole-based heterocycles, Synthetic Communications, 50(13), 2066–2077, 2020.
  • Gacche, R.N., Dhole, N.A., Kamble, S.G., & Bandgar, B.P., In-vitro evaluation of selected chalcones for antioxidant activity, Journal of Enzyme Inhibition and Medicinal Chemistry, 23(1), 28–31, 2008.
  • Kim, B.T., Chun, J.C., & Hwang, K.J., Synthesis of dihydroxylated chalcone derivatives with diverse substitution patterns and their radical scavenging ability toward DPPH free radicals, Bulletin of the Korean Chemical Society, 29(6), 1125-1130, 2008.

Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities

Year 2025, Volume: 15 Issue: 1, 1 - 16, 01.07.2025

Hakan Aslan , Cumhur Avşar

https://doi.org/10.37094/adyujsci.1584171

Abstract

In this study, the Knoevenagel condensation reactions of 3-(heteroaryl)-3-oxopropanenitriles and various aromatic/heteroaromatic aldehydes via L-proline were performed. In these reactions, α-cyanochalcone compounds were obtained in mid-good yields. Spectroscopic techniques were used to clarify the compounds' structures. Both the disc-diffusion method and the minimum inhibitory concentration (MIC) method were used to assess the antibacterial and antifungal properties of all product. Compound 1c, containing the pyridin-3-yl group, exhibited broad-spectrum properties by acting against all bacteria and fungi tested. The antioxidant activities of the compounds were tested by DPPH radical scavenging assay and according to the results of antioxidant activities, the most effective compound among all was found to be 1c. It is possible to say that compounds 1b and 1d also have moderate antioxidant activity.

Keywords

α-cyanochalcone Knoevenagel condensation Antimicrobial activity Antioxidant activity

Ethical Statement

The work does not require ethics committee approval and any private permission.

Supporting Institution

Sinop University Scientific Research Projects Coordination Unit

Project Number

FEF-1901-21-001

Thanks

This work was supported by the Sinop University Scientific Research Projects Coordination Unit under Grant Number FEF-1901-21-001 and we would like to thank to Sinop University for its financial support.

References

  • Sahu, K.N., Balbhadra, S.S., Choudhary, J., & Kohli, D., Exploring pharmacological significance of chalcone scaffold: a review, Current Medicinal Chemistry, 19(2), 209-225, 2012.
  • Rammohan, A., Reddy, J.S., Sravya, G., Rao, C.N., & Zyryanov, G.V., Chalcone synthesis, properties and medicinal applications:a review, Environmental Chemistry Letters, 18, 433-458, 2020.
  • Nayak, Y.N., Gaonkar, S.L., & Sabu, M., Chalcones:Versatile intermediates in heterocyclic synthesis, Journal of Heterocyclic Chemistry, 60(8), 1301-1325, 2023.
  • Khider, A.K., In vivo Antimicrobial Activity of 1 (4-(4-chlorobenzyloxy) phenyl)-3-(4-methyl Phenyl)-2-propen-1-ones (Chalcone 2) Against klebsiella pneumoniae Isolated from Pneumonia Patients, British Journal of Pharmacology and Toxicology, 2(2), 92-96, 2011.
  • Asiri, A.M., & Khan, S.A., Synthesis and anti-bacterial activities of a bis-chalcone derived from thiophene and its bis-cyclized products, Molecules, 16(1), 523-531, 2011.
  • Edwards, M.L., Stemerick, D.M., & Sunkara, P.S., Chalcones: a new class of antimitotic agents, Journal of Medicinal Chemistry, 33(7), 1948-1954, 1990.
  • Mohamed, M.F., & Abuo-Rahma, G.E.D.A., Molecular targets and anticancer activity of quinoline–chalcone hybrids: Literature review, RSC advances, 10(52), 31139-31155, 2020.
  • Ouyang, Y., Li, J., Chen, X., Fu, X., Sun, S., & Wu, Q., Chalcone derivatives: role in anticancer therapy, Biomolecules, 11(6), 894, 2021.
  • Pereira, R., Silva, A.M., Ribeiro, D., Silva, V.L., & Fernandes, E., Bis-chalcones: A review of synthetic methodologies and anti-inflammatory effects, European Journal of Medicinal Chemistry, 252, 115280, 2023.
  • Siddiqa, A., Tajammal, A., Irfan, A., Azam, M., Munawar, M.A., Hardy, R.S., et al., Synthesis, molecular docking, bio-evaluation and quantitative structure activity relationship of new chalcone derivatives as antioxidants, Journal of Molecular Structure, 1277, 134814, 202.
  • Yamamoto, T., Yoshimura, M., Yamaguchi, F., Kouchi, T., Tsuji, R., Saito, M., et al., Anti-allergic activity of naringenin chalcone from a tomato skin extract, Bioscience, Biotechnology, and Biochemistry, 68(8), 1706-1711, 2004.
  • Mahapatra, D.K., Asati, V., & Bharti, S.K., Chalcones and their therapeutic targets for the management of diabetes: structural and pharmacological perspectives, European journal of Medicinal Chemistry, 92, 839-865, 2015.
  • Kumar, H., Devaraji, V., Joshi, R., Jadhao, M., Ahirkar, P., Prasath, R., et al., Antihypertensive activity of a quinoline appended chalcone derivative and its site specific binding interaction with a relevant target carrier protein, RSC Advances, 5(80), 65496-65513, 2015.
  • Aslan, H., Yetişsin, F., Korkmaz, A., Bursal, E., Design, Synthesis, Characterization, Enzyme Inhibition, Molecular Docking, and Pharmacological Evaluation of New Chalcone‐Sulfonate Derivatives Bearing Thiophene, ChemistrySelect, 9(14), e202400053, 2024.
  • Korkmaz, A., Design, synthesis, characterization, molecular docking studies, molecular properties, toxicity, and bioactivity score prediction evaluation of novel chalcone-sulfonate hybrid derivatives, Journal of Molecular Structure, 1286, 135597, 2023.
  • Singh, G., Arora, A., Kalra, P., Maurya, I.K., Ruizc, C.E., Estebanc, M.A., et al., A strategic approach to the synthesis of ferrocene appended chalcone linked triazole allied organosilatranes: Antibacterial, antifungal, antiparasitic and antioxidant studies, Bioorganic & Medicinal Chemistry, 27(1), 188-195, 2019.
  • Guantai, E.M., Ncokazi, K., Egan, T.J., Gut, J., Rosenthal, P.J., Bhampidipati, R., et al., Enone–and chalcone–chloroquinoline hybrid analogues: in silico guided design, synthesis, antiplasmodial activity, in vitro metabolism, and mechanistic studies, Journal of Medicinal Chemistry, 54(10), 3637-3649, 2011.
  • Al‐Rifai, N.M., & Mubarak, M.S., α‐Substituted Chalcones:A Key Review, ChemistrySelect, 6(46), 13224-13252, 2021.
  • Kumar, D., Kumar, N.M., Tantak, M.P., Ogura, M., Kusaka, E., & Ito, T., Synthesis and identification of α-cyano bis (indolyl) chalcones as novel anticancer agents, Bioorganic & Medicinal Chemistry Letters, 24(22), 5170-5174, 2014.
  • Fahim, A.M., & Farag, A.M. Synthesis, antimicrobial evaluation, molecular docking and theoretical calculations of novel pyrazolo [1,5-a] pyrimidine derivatives, Journal of Molecular Structure, 1199, 127025, 2020.
  • Yilmaz, M., Uzunalioğlu, N., Yakut, M., & Pekel, A.T., Oxidative cyclisation of 3-oxopropanenitriles mediated manganese (III) acetate with 2-thienyl substituted alkenes, Turkish Journal of Chemistry, 32(4), 411-422, 2008.
  • Amancha, P.K., Lai, Y.C., Chen, I.C., Liu, H.J., & Zhu, J.L., Diels–Alder reactions of acyclic α-cyano α, β-alkenones: a new approach to highly substituted cyclohexene system, Tetrahedron, 66(4), 871-877, 2010.
  • Stagos, D., Soulitsiotis, N., Tsadila, C., Papaeconomou, S., Arvanitis, C., Ntontos, A., et al., Antibacterial and antioxidant activity of different types of honey derived from Mount Olympus in Greece, International Journal of Molecular Medicine, 42(2), 726-734, 2018.
  • Mama, M., Teshome, T., & Detamo, J., Antibacterial Activity of Honey against Methicillin-Resistant Staphylococcus aureus: A Laboratory-Based Experimental Study, International Journal of Microbiology, 2019, 7686130, 2019.
  • Blois, M.S., Antioxidant determinations by the use of a stable free radical, Nature, 181(4617), 1199-1200, 1958.
  • Kumar, L.S., Prasad, K.S., & Revanasiddappa, H.D., Synthesis, characterization, antioxidant, antimicrobial, DNA binding and cleavage studies of mononuclear Cu (II) and Co (II) complexes of 3-hydroxy-N'-(2-hydroxybenzylidene)-2-naphthohydrazide, European Journal of Chemistry, 2(3), 394-403, 2011.
  • Ma, L., Yuan, L., Xu, C., Li, G., Tao, M., & Zhang, W., An efficient synthesis of 2-aminothiophenes via the Gewald reaction catalyzed by an N-methylpiperazine-functionalized polyacrylonitrile fiber, Synthesis, 45(01), 45-52, 2013.
  • El-Shenawy, A.I., Synthesis and in vitro antibacterial evaluation of some novel annulated quinazolinone derivatives, Russian Journal of General Chemistry, 88, 1712-1719, 2018.
  • Mohamed, M.F., Ibrahim, N.S., Saddiq, A.A., & Abdelhamid, I.A., Novel 3-(pyrazol-4-yl)-2-(1 H-indole-3-carbonyl) acrylonitrile derivatives induce intrinsic and extrinsic apoptotic death mediated P53 in HCT116 colon carcinoma, Scientific Reports, 13(1), 22486, 2023.
  • Bhale, P.S., Shringare, S.N., Khade, A.B., Chavan, H.V., Synthesis, Characterization and Biological Evaluation of Indole-Pyrazole Amalgamated α-Cyano Substituted Chalcones, Anti-Cancer Agents in Medicinal Chemistry, 21(16), 2216-2223, 2021.
  • Bhale, P.S., Chavan, H.V., Endait, R.S., Kadam, A.T., Bopalkar, R.J., & Gaikwad, M.S., Synthesis and Biological Evaluation of Indolyl Bis-chalcones as Anti-Breast Cancer and Antioxidant Agents, Croatica Chemica Acta, 94(1), 35-41, 2021.
  • Zlotnikov, I.D., Krylov, S.S., Belogurova, N.G., Blinnikov, A.N., Kalugin, V.E., & Kudryashova, E.V., New Derivatives of Chalcones, Chromens and Stilbenoids, Complexed with Methyl-β-Cyclodextrin, Show Antioxidant Properties and Antibacterial Synergism with Antibiotics, Biophysica, 4(4), 667-694, 2024.
  • Sallam, H.A., Elgubbi, A.S., & El-Helw, E.A.E., Synthesis and antioxidant screening of new 2-cyano-3-(1,3-diphenyl-1H-pyrazol-4-yl)acryloyl amide derivatives and some pyrazole-based heterocycles, Synthetic Communications, 50(13), 2066–2077, 2020.
  • Gacche, R.N., Dhole, N.A., Kamble, S.G., & Bandgar, B.P., In-vitro evaluation of selected chalcones for antioxidant activity, Journal of Enzyme Inhibition and Medicinal Chemistry, 23(1), 28–31, 2008.
  • Kim, B.T., Chun, J.C., & Hwang, K.J., Synthesis of dihydroxylated chalcone derivatives with diverse substitution patterns and their radical scavenging ability toward DPPH free radicals, Bulletin of the Korean Chemical Society, 29(6), 1125-1130, 2008.
There are 35 citations in total.

Details

Primary Language English
Subjects Bacteriology, Organic Chemical Synthesis
Journal Section Biology
Authors

Hakan Aslan 0000-0002-5268-7196

Cumhur Avşar 0000-0002-4095-0022

Project Number FEF-1901-21-001
Early Pub Date April 7, 2025
Publication Date July 1, 2025
Submission Date November 13, 2024
Acceptance Date February 14, 2025
Published in Issue Year 2025 Volume: 15 Issue: 1

Cite

APA Aslan, H., & Avşar, C. (2025). Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities. Adıyaman University Journal of Science, 15(1), 1-16. https://doi.org/10.37094/adyujsci.1584171
AMA Aslan H, Avşar C. Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities. ADYU J SCI. July 2025;15(1):1-16. doi:10.37094/adyujsci.1584171
Chicago Aslan, Hakan, and Cumhur Avşar. “Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities”. Adıyaman University Journal of Science 15, no. 1 (July 2025): 1-16. https://doi.org/10.37094/adyujsci.1584171.
EndNote Aslan H, Avşar C (July 1, 2025) Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities. Adıyaman University Journal of Science 15 1 1–16.
IEEE H. Aslan and C. Avşar, “Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities”, ADYU J SCI, vol. 15, no. 1, pp. 1–16, 2025, doi: 10.37094/adyujsci.1584171.
ISNAD Aslan, Hakan - Avşar, Cumhur. “Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities”. Adıyaman University Journal of Science 15/1 (July 2025), 1-16. https://doi.org/10.37094/adyujsci.1584171.
JAMA Aslan H, Avşar C. Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities. ADYU J SCI. 2025;15:1–16.
MLA Aslan, Hakan and Cumhur Avşar. “Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities”. Adıyaman University Journal of Science, vol. 15, no. 1, 2025, pp. 1-16, doi:10.37094/adyujsci.1584171.
Vancouver Aslan H, Avşar C. Synthesis, Characterization of α-Cyanochalcone Compounds and Determination of Their Antibacterial, Antifungal and Antioxidant Activities. ADYU J SCI. 2025;15(1):1-16.

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