Sintesis Dan Uji Aktivitas Antioksidan Senyawa Pirazolo-Piridin Analog Kurkumin Monoketon
Keywords:
Analog kurkumin monoketon, Claisen schmidt, refluks, docking molekuler, DPPH.
Abstract
Telah dilakukan sintesis senyawa pirazolo-piridin analog kurkumin monoketeon dengan dua tahap reaksi. Tahap pertama dilakukan reaksi sintesis analog kurkumin dengan metode microwave dengan prinsip reaksi Claisen-Schmidt. Tahap kedua dengan senayawa analog kurkumin hasil sintesa tahap satu ditambah phenyl hidrazin memakai metode refluks pada temperatur 800C. Struktur senyawa 1 telah ditetapkan dengan analisis spektroskopi, meliputi spektroskopi UV, FT-IR, 1H-NMR, dan COSY. Uji aktivitas antioksidan dilakukan dengan metode DPPH(1-1diphenyl-2-picryl hydrazyl). Hasil uji aktivitas antioksidan secara in vitro menunjukkan senyawa 1 aktif sebagai anti oksidan dengan nilai IC50; 190,809 µg/ml. Docking molekuler dilakukan menggunakan paket perangkat lunak MOE 2020.09, dan hasil docking molecular, senyawa 1 dapat digunakan sebagai calon antioksidan yang potensial.
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References
1. Tan.B.L.b , Mohd Esa Norhaizan, Winnie-Pui-Pui Liew1 and Heshu Sulaiman Rahman Antioxidant and Oxidative Stress: A Mutual Interplay in Age-Related Diseases, REVIEW , published: 16 October 2018
doi: 10.3389/fphar.2018.01162
2. Brainina.K, Natalia Stozhko 1 and Marina Vidrevich, 2019, Antioxidants: Terminology, Methods, and Future Considerations, Project Report, Antioxidants 2019, 8, 297; doi:10.3390/antiox8080297 , www.mdpi.com/journal/antioxidants.
3. Zuo, L., Zhou, T., Pannell, B. K., Ziegler, A., and Best, T. M , 2015. Biological and physiological role of reactive oxygen species–the good, the bad and the ugly. Acta Physiol. 214, 329–348. doi: 10.1111/apha.12515.
4. Liu, Z., Zhou, T., Ziegler, A. C., Dimitrion, P., and Zuo, L. 2017. Oxidative stress in neurodegenerative diseases: from molecular mechanisms to clinical applications. Oxid. Med. Cell. Longev. 2017:2525967. doi: 10.1155/2017/2525967
5. Tan, B. L.a., Norhaizan, M. E., Huynh, K., Yeap, S. K., Hazilawati, H., and Roselina, K. 2015. Brewers’ rice modulates oxidative stress in azoxymethane mediated colon carcinogenesis in rats. World J. Gastroenterol. 21, 8826–8835. doi: 10.3748/wjg.v21.i29.8826
6. Kostopoulou.I, Antonia Diassakou,Eleni Kavetsou,Eftichia Kritsi, Panagiotis Zoumpoulakis, Eleni Pontiki, Dimitra Hadjipavlou Litina, Anastasia Detsi, “Novel quinolinone–pyrazoline hybrids: synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity” Molecular Diversity ORIGINAL ARTICLE , https://doi.org/10.1007/s11030-020-10045-x.
7. Sánchez.J.P, Villamil Paula K. Bautista-Niño,1 Norma C. Serrano,Melvin Y. Rincon,1 and Nisha J. Garg, 2020, Review Article, Potential Role of Antioxidants as Adjunctive Therapy in Chagas Disease, Hindawi , Oxidative Medicine and Cellular Longevity , Volume 2020, Article ID 9081813, 13 pages , https://doi.org/10.1155/2020/9081813
8. Pilar de T. M, Rita Yolanda Cavero , , María Isabel Calvo 1,3,* and José Luis Vizmanos, 2019, A Simple and a Reliable Method to Quantify Antioxidant Activity In Vivo, Antioxidants 2019, 8, 142.
9. Kumar.A, Bhat G. Varadaraj, Rajeev K. Singla, 2013, Synthesis and evaluation of antioxidant activity of novel 3,5-disubstituted-2-pyrazolines, Bulletin of Faculty of Pharmacy, Cairo University (2013) 51, 167–173.
10. Moukette. B, Constant Anatole Pieme, Jacques Romain Njimou, Cabral Prosper Nya Biapa, Bravi Marco and Jeanne Yonkeu Ngogang, 2015, In vitro antioxidant properties, free radicals scavenging activities of extracts and polyphenol composition of a non-timber forest product used as spice: Monodora myristica, Biological Research (2015) 48:15, DOI 10.1186/s40659-015-0003-1
11. Ansari, A, Abad Ali, Mohd Asif and Shamsuzzaman, 2017, Review: biologically active pyrazole derivatives , New J. Chem., 2017, 41, 16--41
12. Behbehani .H, and Hamada Mohamed Ibrahim , 2019, Synthetic Strategy for Pyrazolo[1,5 a]pyridine and Pyrido[1,2 b]indazole Derivatives through AcOH and O2 Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and N Amino-2-iminopyridines, ACS Omega 2019, 4, 15289−15303, http://pubs.acs.org/journal/acsodf
13. Spiegel. M, Tadeusz Andruniów,and Zbigniew Sroka, 2020, Flavones’ and Flavonols’ Antiradical Structure–Activity Relationship—A Quantum Chemical Study , Antioxidants, 2020, 9, 461; doi:10.3390/antiox9060461
14. Ali. S A., Samir Mohamed Awad , Ahmed Mohammed Said , Shahenda Mahgoub, Heba Tahaa and Naglaa Mohamed Ahmed , 2020 , Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors , Journal Of Enzym Inhibition and Medicinal Chemistry , 2020, VOL. 35, NO. 1, 847–863 , https://doi.org/10.1080/14756366.2020.1742116
15. Jin Lee. K, You Chang Oh, Won Kyung Cho, and Jin Yeul Ma, 2015, Research Article Antioxidant and Anti-Inflammatory Activity Determination of One Hundred Kinds of Pure Chemical Compounds Using Offline and Online Screening HPLC Assay , Hindawi Publishing Corporation , Evidence-Based Complementary and Alternative Medicine Volume 2015, Article ID 165457, 13 pages , http://dx.doi.org/10.1155/2015/165457
16. Brullo C., Matteo Massa , Federica Rapetti , Silvana Alfei , Maria B. Bertolotto , Fabrizio Montecucco, Maria Grazia Signorello 4 and Olga Bruno, 2020, Hybrid Pyrazole and Imidazopyrazole Antinflflammatory Agents Able to Reduce ROS Production in Difffferent Biological Targets, Molecules 2020, 25, 899; doi:10.3390/molecules25040899
17. Frimayanti N, Mora E, & Anugrah R. Study of Molecular Docking of Chalcone Analoque Compound as Inhibitors for Liver Cancer Cells HepG2. Comp Eng Appl J. 2018; 7(2): 137-147
18. L.Perrin.C, and Kuei-Lin Chang, 2016, The Complete Mechanism of an Aldol Condensation ; J. Org. Chem., Just Accepted Manuscript DOI: 10.1021/acs.joc.6b00959 , Publication Date (Web): 09 Jun 2016
19. Nagargoje, Amol.A, Satish V. Akolkar, Madiha M. Siddiqui, Aditi V. Bagade , 2019, Synthesis and evaluation of pyrazole-incorporated monocarbonyl curcumin analogues as antiproliferative and antioxidant agents , Journal Chin Chem Soc. 2019;1–8.
20. Pawelczyk, A., Sowa-Kasprzak, K., Olender, D., dan Zaprutko, L. 2018. Molecular Consortia-Various Structural and Synthesis Concepts for More Effective Tharapeutics Synthesis. Internasional Journal of Molecular Sciences. 1(1): 2-17.
21. Zamri, A.; Teruna, H.Y.; Ikhtiarudin, I. The influences of power variations on selectivity of synthesis reaction of 2′-hydroxychalcone analogue under microwave irradiation. Molekul 2016, 11, 299–307,doi:10.20884/1.jm.2016.11.2.220
doi: 10.3389/fphar.2018.01162
2. Brainina.K, Natalia Stozhko 1 and Marina Vidrevich, 2019, Antioxidants: Terminology, Methods, and Future Considerations, Project Report, Antioxidants 2019, 8, 297; doi:10.3390/antiox8080297 , www.mdpi.com/journal/antioxidants.
3. Zuo, L., Zhou, T., Pannell, B. K., Ziegler, A., and Best, T. M , 2015. Biological and physiological role of reactive oxygen species–the good, the bad and the ugly. Acta Physiol. 214, 329–348. doi: 10.1111/apha.12515.
4. Liu, Z., Zhou, T., Ziegler, A. C., Dimitrion, P., and Zuo, L. 2017. Oxidative stress in neurodegenerative diseases: from molecular mechanisms to clinical applications. Oxid. Med. Cell. Longev. 2017:2525967. doi: 10.1155/2017/2525967
5. Tan, B. L.a., Norhaizan, M. E., Huynh, K., Yeap, S. K., Hazilawati, H., and Roselina, K. 2015. Brewers’ rice modulates oxidative stress in azoxymethane mediated colon carcinogenesis in rats. World J. Gastroenterol. 21, 8826–8835. doi: 10.3748/wjg.v21.i29.8826
6. Kostopoulou.I, Antonia Diassakou,Eleni Kavetsou,Eftichia Kritsi, Panagiotis Zoumpoulakis, Eleni Pontiki, Dimitra Hadjipavlou Litina, Anastasia Detsi, “Novel quinolinone–pyrazoline hybrids: synthesis and evaluation of antioxidant and lipoxygenase inhibitory activity” Molecular Diversity ORIGINAL ARTICLE , https://doi.org/10.1007/s11030-020-10045-x.
7. Sánchez.J.P, Villamil Paula K. Bautista-Niño,1 Norma C. Serrano,Melvin Y. Rincon,1 and Nisha J. Garg, 2020, Review Article, Potential Role of Antioxidants as Adjunctive Therapy in Chagas Disease, Hindawi , Oxidative Medicine and Cellular Longevity , Volume 2020, Article ID 9081813, 13 pages , https://doi.org/10.1155/2020/9081813
8. Pilar de T. M, Rita Yolanda Cavero , , María Isabel Calvo 1,3,* and José Luis Vizmanos, 2019, A Simple and a Reliable Method to Quantify Antioxidant Activity In Vivo, Antioxidants 2019, 8, 142.
9. Kumar.A, Bhat G. Varadaraj, Rajeev K. Singla, 2013, Synthesis and evaluation of antioxidant activity of novel 3,5-disubstituted-2-pyrazolines, Bulletin of Faculty of Pharmacy, Cairo University (2013) 51, 167–173.
10. Moukette. B, Constant Anatole Pieme, Jacques Romain Njimou, Cabral Prosper Nya Biapa, Bravi Marco and Jeanne Yonkeu Ngogang, 2015, In vitro antioxidant properties, free radicals scavenging activities of extracts and polyphenol composition of a non-timber forest product used as spice: Monodora myristica, Biological Research (2015) 48:15, DOI 10.1186/s40659-015-0003-1
11. Ansari, A, Abad Ali, Mohd Asif and Shamsuzzaman, 2017, Review: biologically active pyrazole derivatives , New J. Chem., 2017, 41, 16--41
12. Behbehani .H, and Hamada Mohamed Ibrahim , 2019, Synthetic Strategy for Pyrazolo[1,5 a]pyridine and Pyrido[1,2 b]indazole Derivatives through AcOH and O2 Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and N Amino-2-iminopyridines, ACS Omega 2019, 4, 15289−15303, http://pubs.acs.org/journal/acsodf
13. Spiegel. M, Tadeusz Andruniów,and Zbigniew Sroka, 2020, Flavones’ and Flavonols’ Antiradical Structure–Activity Relationship—A Quantum Chemical Study , Antioxidants, 2020, 9, 461; doi:10.3390/antiox9060461
14. Ali. S A., Samir Mohamed Awad , Ahmed Mohammed Said , Shahenda Mahgoub, Heba Tahaa and Naglaa Mohamed Ahmed , 2020 , Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors , Journal Of Enzym Inhibition and Medicinal Chemistry , 2020, VOL. 35, NO. 1, 847–863 , https://doi.org/10.1080/14756366.2020.1742116
15. Jin Lee. K, You Chang Oh, Won Kyung Cho, and Jin Yeul Ma, 2015, Research Article Antioxidant and Anti-Inflammatory Activity Determination of One Hundred Kinds of Pure Chemical Compounds Using Offline and Online Screening HPLC Assay , Hindawi Publishing Corporation , Evidence-Based Complementary and Alternative Medicine Volume 2015, Article ID 165457, 13 pages , http://dx.doi.org/10.1155/2015/165457
16. Brullo C., Matteo Massa , Federica Rapetti , Silvana Alfei , Maria B. Bertolotto , Fabrizio Montecucco, Maria Grazia Signorello 4 and Olga Bruno, 2020, Hybrid Pyrazole and Imidazopyrazole Antinflflammatory Agents Able to Reduce ROS Production in Difffferent Biological Targets, Molecules 2020, 25, 899; doi:10.3390/molecules25040899
17. Frimayanti N, Mora E, & Anugrah R. Study of Molecular Docking of Chalcone Analoque Compound as Inhibitors for Liver Cancer Cells HepG2. Comp Eng Appl J. 2018; 7(2): 137-147
18. L.Perrin.C, and Kuei-Lin Chang, 2016, The Complete Mechanism of an Aldol Condensation ; J. Org. Chem., Just Accepted Manuscript DOI: 10.1021/acs.joc.6b00959 , Publication Date (Web): 09 Jun 2016
19. Nagargoje, Amol.A, Satish V. Akolkar, Madiha M. Siddiqui, Aditi V. Bagade , 2019, Synthesis and evaluation of pyrazole-incorporated monocarbonyl curcumin analogues as antiproliferative and antioxidant agents , Journal Chin Chem Soc. 2019;1–8.
20. Pawelczyk, A., Sowa-Kasprzak, K., Olender, D., dan Zaprutko, L. 2018. Molecular Consortia-Various Structural and Synthesis Concepts for More Effective Tharapeutics Synthesis. Internasional Journal of Molecular Sciences. 1(1): 2-17.
21. Zamri, A.; Teruna, H.Y.; Ikhtiarudin, I. The influences of power variations on selectivity of synthesis reaction of 2′-hydroxychalcone analogue under microwave irradiation. Molekul 2016, 11, 299–307,doi:10.20884/1.jm.2016.11.2.220
Published
2023-04-14
How to Cite
Mora, E., Zamri, A., Teruna, H. Y., Frimayanti, N., Ikhtiarudin, I., Herfindo, N., & Natia, E. (2023). Sintesis Dan Uji Aktivitas Antioksidan Senyawa Pirazolo-Piridin Analog Kurkumin Monoketon. Jurnal Penelitian Dan Pengkajian Ilmiah Eksakta, 2(1), 116-120. https://doi.org/10.47233/jppie.v2i1.798
Section
Articles
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