Research Article
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Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives

Year 2022, Volume 26, Issue 6, 1224 - 1232, 31.12.2022

Abstract

In this study, novel furfuryl-chalcone derivatives substituted sulfonyl chloride or sulphonamide were synthesized. Their antioxidant properties were investigated via DPPH and ABTS assays. All furfuryl-chalcones had high antioxidant properties. Among them, (E)-5-(3-(4-(chlorosulfonyl)-3-hydroxyphenyl)-3-oxoprop-1-en-1-yl)furan-2-sulfonyl chloride (4e) and (E)-5-(3-(3-(chlorosulfonyl)-4-hydroxyphenyl)-3-oxoprop-1-en-1-yl)furan-2-sulfonyl chloride (4d) exhibited the highest DPPH activity with the IC50 values of 4.23 μM and 6.68 μM, respectively, which are almost 2- and 1.5-fold more than quercetin activity (IC50 = 8.69 μM), well-known as antioxidant agent and used as a standard. Also, 4e and 4d had the highest ABTS activity with the IC50 value of 5.55 μM and 7.84 μM, respectively, which are almost 2.8- and 2-fold higher than that of quercetin (IC50 = 15.49 μM). The structure-activity relationship results revealed that most of synthesized sulfonyl chloride derivatives (4a-e) have higher antioxidant activity than the sulphonamide derivatives (5a-c) and also 4d and 4e, including hydroxyl group, exhibited the strongest antioxidant activity as expected.

References

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  • N. Zhang, P. Hu, Y. Wang, Q. Tang, Q. Zheng, Z. Wang, Y. He, “A reactive oxygen species (ROS) activated hydrogen sulfide (H2S) donor with self-reporting fluorescence”, ACS Sensors, vol. 5, pp. 319-326, 2020.
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  • P. Singh, A. Anand, V. Kumar, “Recent developments in biological activities of chalcones: A mini review”, European Journal of Medicinal Chemistry, vol. 85, pp. 758-777, 2014.
  • A. Atahan, “Synthesis and characterisation of polyaromatic chalcones with electron donation”, Sakarya University Journal of Science, vol. 24, no. 2, pp. 347-356, 2020.
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  • F. Gao, G. Huang, J. Xiao, “Chalcone hybrids as potential anticancer agents: Current development, mechanism of action, and structure‐activity relationship”, Medical Research Reviews, vol. 40, pp. 2049-2084, 2020.
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  • P. Dandawate, K. Ahmed, S. Padhye, A. Ahmad, B. Biersack, “Anticancer active heterocyclic chalcones: recent developments”, Anti-Cancer Agents in Medicinal Chemistry, vol. 21, pp. 558-566, 2021.
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  • F. Sonmez, Z. Gunesli, B. Z. Kurt, I. Gazioglu, D. Avci, M. Kucukislamoglu, “Synthesis, antioxidant activity and SAR study of novel spiro-isatin-based Schiff bases”, Molecular Diversity, vol. 23, pp. 829–844, 2019.
  • B. Zengin Kurt, "Sinnamaldehitin yeni schiff bazlarının sentezi ve antioksidan özelliklerinin incelenmesi", Sakarya University Journal of Science, vol. 22, no. 3, pp. 1024-1032, 2018.
  • H. Muğlu, B. Zengin Kurt, F. Sönmez, E. Güzel, M. S. Çavuş, H. Yakan, “Preparation, antioxidant activity, and theoretical studies on the relationship between antioxidant and electronic properties of bis(thio/carbohydrazone) derivatives”, Journal of Physics and Chemistry of Solids, vol.164, 110618, 2022.
  • I. Gazioglu, B. Zengin Kurt, E. Sevgi, F. Sonmez, “Anticholinesterase, antioxidant, antiaflatoxigenic activities of ten edible wild plants from Ordu area, Turkey”, Iranian Journal of Pharmaceutical Research, vol. 17, pp. 1047-1056, 2018.
  • N. Belkheiri, B. Bouguerne, F. Bedos-Belval, H. Duran, C. Bernis, R. Salvayre, A. Negre-Salvayre, M. Baltas, “Synthesis and antioxidant activity evaluation of a syringic hydrazones family”, European Journal of Medicinal Chemistry, vol. 45, 3019-3026, 2010.
  • B. D. Kumar, D. S. Rawat, “Synthesis and antioxidant activity of thymol and carvacrol based Schiff bases”, Bioorganic and Medicinal Chemistry Letters, vol. 23, pp. 641–645, 2013.
  • A. M. Campos, E. A. Lissi, “Kinetics of the reaction between 2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) derived radical cations and phenols”, International Journal of Chemical Kinetics, vol. 29, pp. 219-224, 1997.
  • T. Herraiz, J. Galisteo, “Endogenous and dietary indoles: A class of antioxidants and radical scavengers in the ABTS assay”, Free Radical Research, vol. 38, pp. 323-331, 2004.
  • A. Atahan, N. Gencer, C. Bilen, E. Yavuz, H. Genc, F. Sonmez, M. Zengin, M. Ceyhan, M. Kucukislamoglu, “Synthesis, biological activity and structure-activity relationship of novel diphenylurea derivatives containing tetrahydroquinoline as carbonic anhydrase I and II inhibitors”, ChemistrySelect, vol. 3, pp. 529–534, 2018.

Year 2022, Volume 26, Issue 6, 1224 - 1232, 31.12.2022

Abstract

References

  • J. D. Hayes, A.T. Dinkova-Kostova, K. D. Tew, “Oxidative stress in cancer”, Cancer Cells, vol. 38, pp. 167-197, 2020.
  • A. M. Pisoschi, A. Pop, F. Iordache, L. Stanca, G. Predoi, A. I. Serban, “Oxidative stress mitigation by antioxidants-an overview on their chemistry and influences on health status”, European Journal of Medicinal Chemistry, vol. 209, 112891, 2021.
  • H. Sies, D. P. Jones, “Reactive oxygen species (ROS) as pleiotropic physiological signalling agents”, Nature Reviews Molecular Cell Biology, vol. 21, pp. 363-383, 2020.
  • N. Zhang, P. Hu, Y. Wang, Q. Tang, Q. Zheng, Z. Wang, Y. He, “A reactive oxygen species (ROS) activated hydrogen sulfide (H2S) donor with self-reporting fluorescence”, ACS Sensors, vol. 5, pp. 319-326, 2020.
  • M. V. Irazabal, V. E. Torres, “Reactive oxygen species and redox signaling in chronic kidney disease”, Cells, vol. 9, 1342, 2020.
  • A. Kirtonia, G. Sethi, M. Garg, “The multifaceted role of reactive oxygen species in tumorigenesis”, Cellular and Molecular Life Sciences, vol. 77, pp. 4459–4483, 2020.
  • B. Z. Kurt, I. Gazioglu, N. O. Kandas, F. Sonmez, “Synthesis, anticholinesterase, antioxidant, and anti-aflatoxigenic activity of novel coumarin carbamate derivatives”, ChemistrySelect, vol. 3, pp. 3978–3983, 2018.
  • B. Z. Kurt, I. Gazioglu, F. Sonmez, M. Kucukislamoglu, “Synthesis, antioxidant and anticholinesterase activities of novel coumarylthiazole derivatives”, Bioorganic and Medicinal Chemistry, vol. 59, pp. 80–90, 2015.
  • N. Sahu, S. Balbhadra, J. Choudhary, D. Kohli, “Exploring pharmacological significance of chalcone scaffold: a review”, Current Medicinal Chemistry, vol. 19, pp. 209-225, 2012.
  • P. Singh, A. Anand, V. Kumar, “Recent developments in biological activities of chalcones: A mini review”, European Journal of Medicinal Chemistry, vol. 85, pp. 758-777, 2014.
  • A. Atahan, “Synthesis and characterisation of polyaromatic chalcones with electron donation”, Sakarya University Journal of Science, vol. 24, no. 2, pp. 347-356, 2020.
  • W. Dan, J. Dai, “Recent developments of chalcones as potential antibacterial agents in medicinal chemistry”, European Journal of Medicinal Chemistry, vol. 187, 111980, 2020.
  • F. Gao, G. Huang, J. Xiao, “Chalcone hybrids as potential anticancer agents: Current development, mechanism of action, and structure‐activity relationship”, Medical Research Reviews, vol. 40, pp. 2049-2084, 2020.
  • S. Verma, A. K. Srivastava, O. P. Pandey, “A review on chalcones synthesis and their biological activity”, PharmaTutor, vol. 6, pp. 22-39, 2018.
  • D. W. Elias, M. A. Beazely, N. M. Kandepu, “Bioactivities of chalcones”, Current Medicinal Chemistry, vol. 6, pp. 1125-1149, 1999.
  • L. Ni, C.Q. Meng, J.A. Sikorski, “Recent advances in therapeutic chalcones”, Expert Opinion on Therapeutic Patents, vol. 14, pp. 1669-1691, 2004.
  • H. Karaca, “Catalytic oxidation of 2-mercaptoethanol by cobalt(II)phthalocyanines bearing chalcone with furan and thiophene”, Sakarya University Journal of Science, vol. 22, no. 6, pp. 1699-1703, 2018.
  • P. Dandawate, K. Ahmed, S. Padhye, A. Ahmad, B. Biersack, “Anticancer active heterocyclic chalcones: recent developments”, Anti-Cancer Agents in Medicinal Chemistry, vol. 21, pp. 558-566, 2021.
  • R. Salotra, D. Utreja, “A comprehensive appraisal of chalcones and their heterocyclic analogs as antimicrobial agents”, Current Organic Chemistry, vol. 24, pp. 2755-2781, 2020.
  • C. Kesari, K. R. Rama, K. Sedighi, J. Stenvang, F. Björkling, S. Kankala, N. Thota, “Synthesis of thiazole linked chalcones and their pyrimidine analogues as anticancer agents”, Synthetic Communications, vol. 51, pp. 1406-1416, 2021.
  • F. Sonmez, Z. Gunesli, B. Z. Kurt, I. Gazioglu, D. Avci, M. Kucukislamoglu, “Synthesis, antioxidant activity and SAR study of novel spiro-isatin-based Schiff bases”, Molecular Diversity, vol. 23, pp. 829–844, 2019.
  • B. Zengin Kurt, "Sinnamaldehitin yeni schiff bazlarının sentezi ve antioksidan özelliklerinin incelenmesi", Sakarya University Journal of Science, vol. 22, no. 3, pp. 1024-1032, 2018.
  • H. Muğlu, B. Zengin Kurt, F. Sönmez, E. Güzel, M. S. Çavuş, H. Yakan, “Preparation, antioxidant activity, and theoretical studies on the relationship between antioxidant and electronic properties of bis(thio/carbohydrazone) derivatives”, Journal of Physics and Chemistry of Solids, vol.164, 110618, 2022.
  • I. Gazioglu, B. Zengin Kurt, E. Sevgi, F. Sonmez, “Anticholinesterase, antioxidant, antiaflatoxigenic activities of ten edible wild plants from Ordu area, Turkey”, Iranian Journal of Pharmaceutical Research, vol. 17, pp. 1047-1056, 2018.
  • N. Belkheiri, B. Bouguerne, F. Bedos-Belval, H. Duran, C. Bernis, R. Salvayre, A. Negre-Salvayre, M. Baltas, “Synthesis and antioxidant activity evaluation of a syringic hydrazones family”, European Journal of Medicinal Chemistry, vol. 45, 3019-3026, 2010.
  • B. D. Kumar, D. S. Rawat, “Synthesis and antioxidant activity of thymol and carvacrol based Schiff bases”, Bioorganic and Medicinal Chemistry Letters, vol. 23, pp. 641–645, 2013.
  • A. M. Campos, E. A. Lissi, “Kinetics of the reaction between 2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) derived radical cations and phenols”, International Journal of Chemical Kinetics, vol. 29, pp. 219-224, 1997.
  • T. Herraiz, J. Galisteo, “Endogenous and dietary indoles: A class of antioxidants and radical scavengers in the ABTS assay”, Free Radical Research, vol. 38, pp. 323-331, 2004.
  • A. Atahan, N. Gencer, C. Bilen, E. Yavuz, H. Genc, F. Sonmez, M. Zengin, M. Ceyhan, M. Kucukislamoglu, “Synthesis, biological activity and structure-activity relationship of novel diphenylurea derivatives containing tetrahydroquinoline as carbonic anhydrase I and II inhibitors”, ChemistrySelect, vol. 3, pp. 529–534, 2018.

Details

Primary Language English
Subjects Engineering, Chemical
Journal Section Research Articles
Authors

Fatih SÖNMEZ> (Primary Author)
SAKARYA UYGULAMALI BİLİMLER ÜNİVERSİTESİ
0000-0001-7486-6374
Türkiye


Enes AKGÜN>
SAKARYA ÜNİVERSİTESİ, FEN BİLİMLERİ ENSTİTÜSÜ
0000-0002-2293-925X
Türkiye


Zuhal ŞAHİN>
SAKARYA UYGULAMALI BİLİMLER ÜNİVERSİTESİ
0000-0001-9856-8064
Türkiye

Publication Date December 31, 2022
Submission Date May 23, 2022
Acceptance Date October 17, 2022
Published in Issue Year 2022, Volume 26, Issue 6

Cite

Bibtex @research article { saufenbilder1119766, journal = {Sakarya University Journal of Science}, eissn = {2147-835X}, address = {}, publisher = {Sakarya University}, year = {2022}, volume = {26}, number = {6}, pages = {1224 - 1232}, title = {Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives}, key = {cite}, author = {Sönmez, Fatih and Akgün, Enes and Şahin, Zuhal} }
APA Sönmez, F. , Akgün, E. & Şahin, Z. (2022). Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives . Sakarya University Journal of Science , 26 (6) , 1224-1232 . Retrieved from https://dergipark.org.tr/en/pub/saufenbilder/issue/74051/1119766
MLA Sönmez, F. , Akgün, E. , Şahin, Z. "Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives" . Sakarya University Journal of Science 26 (2022 ): 1224-1232 <https://dergipark.org.tr/en/pub/saufenbilder/issue/74051/1119766>
Chicago Sönmez, F. , Akgün, E. , Şahin, Z. "Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives". Sakarya University Journal of Science 26 (2022 ): 1224-1232
RIS TY - JOUR T1 - Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives AU - FatihSönmez, EnesAkgün, ZuhalŞahin Y1 - 2022 PY - 2022 N1 - DO - T2 - Sakarya University Journal of Science JF - Journal JO - JOR SP - 1224 EP - 1232 VL - 26 IS - 6 SN - -2147-835X M3 - UR - Y2 - 2022 ER -
EndNote %0 Sakarya University Journal of Science Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives %A Fatih Sönmez , Enes Akgün , Zuhal Şahin %T Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives %D 2022 %J Sakarya University Journal of Science %P -2147-835X %V 26 %N 6 %R %U
ISNAD Sönmez, Fatih , Akgün, Enes , Şahin, Zuhal . "Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives". Sakarya University Journal of Science 26 / 6 (December 2022): 1224-1232 .
AMA Sönmez F. , Akgün E. , Şahin Z. Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives. SAUJS. 2022; 26(6): 1224-1232.
Vancouver Sönmez F. , Akgün E. , Şahin Z. Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives. Sakarya University Journal of Science. 2022; 26(6): 1224-1232.
IEEE F. Sönmez , E. Akgün and Z. Şahin , "Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives", Sakarya University Journal of Science, vol. 26, no. 6, pp. 1224-1232, Dec. 2022

Sakarya University Journal of Science (SAUJS)