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Some Heterocyclic Hydrazone Compounds: Synthesis, Spectral Characterization and Anticancer Activity Study

Year 2022, Volume 43, Issue 3, 437 - 442, 30.09.2022
https://doi.org/10.17776/csj.1099217

Abstract

Cancer is currently ongoing to be a significant health problem threatening human health. Hydrazone compounds constitute a popular class of organic compounds used in novel drug discovery studies in therapy of cancer. In the current study, the preparation and structural characterization of some heterocyclic hydrazone compounds (7-12) and their anticancer capacities against HeLa cervical cancer and MCF-7 breast cancer cell lines were reported. The target compounds were characterized by some spectroscopic techniques (1H NMR, 13C NMR and FT-IR). The in vitro cytotoxic potentials of the target molecules were assessed by using MTT assay against two cancer cell lines. L929 mouse fibroblast cell lines were employed as normal cell. The results displayed that some of the tested molecules had varying anticancer activities. Among the tested compounds, compound 8 indicated anticancer activity against HeLa cells with IC50 value of 34.38 µM. On the other hand, of these tested compounds, compound 11 (IC50 = 26.84 µM) displayed anticancer activity against MCF-7 cells.

References

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  • [3] Küpeli Akkol E., Genç Y., Karpuz B., Sobarzo-Sánchez E., Capasso, R., Coumarins and coumarin-related compounds in pharmacotherapy of cancer, Cancers., 12(7) (2020) 1959.
  • [4] Kashyap D., Garg V.K., Sandberg E.N., Goel N., Bishayee, A., Oncogenic and tumor suppressive components of the cell cycle in breast cancer progression and prognosis, Pharmaceutics., 13(4) (2021) 569.
  • [5] Luna J.I., Grossenbacher S.K., Murphy W.J., Canter, R. J., Targeting cancer stem cells with natural killer cell immunotherapy, Expert Opin. Biol. Ther., 17(3) (2017) 313-324.
  • [6] Weiss, T., Weller M., Roth, P., Immunological effects of chemotherapy and radiotherapy against brain tumors, Expert Rev. Anticancer Ther., 16(10) (2016) 1087-1094.
  • [7] Scarpa E.S., Fabrizio G., Di Girolamo M., A role of intracellular mono‐ADP‐ribosylation in cancer biology, The FEBS J., 280(15) (2013) 3551-3562.
  • [8] Mansoori B., Mohammadi A., Davudian S., Shirjang S., Baradaran, B., The different mechanisms of cancer drug resistance: a brief review, Adv. Pharm. Bull., 7(3) (2017) 339-348.
  • [9] Longley D.B., Johnston P.G., Molecular mechanisms of drug resistance, J. Pathol., 205(2) (2005) 275-292.
  • [10] Goodman L.S., Wintrobe M.M., Dameshek W., Goodman M.J., Gilman A., McLennan M.T., Nitrogen mustard therapy: Use of methyl-bis (beta-chloroethyl) amine hydrochloride and tris (beta-chloroethyl) amine hydrochloride for hodgkin's disease, lymphosarcoma, leukemia and certain allied and miscellaneous disorders, JAMA, 132(3) (1946) 126-132.
  • [11] Barinaga M., From bench top to bedside, Sci., 278(5340) (1997) 1036-1039.
  • [12] Calabresi P., Welch A.D., Chemotherapy of neoplastic diseases, Annu. Rev. Med., 13(1) (1962) 147-202.
  • [13] Carter S.K., Slavik M., Chemotherapy of cancer, Annu. Rev. Pharmacol., 14(1) (1974) 157-179.
  • [14] Sung H., Ferlay J., Siegel R.L., Laversanne M., Soerjomataram I., Jemal A., Bray F., Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries, CA cancer J. Clin., 71(3) (2021) 209-249.
  • [15] Cancer, UK, How Chemotherapy Drugs Work. Available at: https://www.cancer.org/treatment/treatments-and-side-effects/treatment-types/chemotherapy/how-chemotherapy-drugs-work.html, 2021 (accessed 28 Mar 2022).
  • [16] Al-Mulla A., A review: biological importance of heterocyclic compounds, Der Pharma Chem., 9(13) (2017) 141-147.
  • [17] Çakmak R., Başaran E., Kaya S., Erkan S., Synthesis, spectral characterization, chemical reactivity and anticancer behaviors of some novel hydrazone derivatives: Experimental and theoretical insights, J. Mol. Struct., 1253 (2022) 132224.
  • [18] Başaran E., Haşimi N., Çakmak R., Çınar E., Synthesis, structural characterization, and biological evaluation of some hydrazone compounds as potential antioxidant agents, Russ. J. Bioorganic Chem., 48(1) (2022) 143-152.
  • [19] Tabbiche A., Bouchama A., Chafai N., Zaidi F., Chiter C., Yahiaoui M., Abiza A., New bis hydrazone: synthesis, x-ray crystal structure, DFT computations, conformational study and in silico study of the ınhibition activity of SARS-CoV-2, J. Mol. Struct., 1261 (2022) 132865.
  • [20] Aydin S., Kaushik-Basu N., Arora P., Basu A., Nichols D.B., Talele T.T., Akkurt M., Çelik I., Büyükgungör O., Kucukguzel Ş.G., Microwave assisted synthesis of some novel flurbiprofen hydrazide-hydrazones as anti-hcv ns5b and anticancer agents, Marmara Pharm. J., 17(1) (2013) 26-34.
  • [21] Şenkardeş S., Türe A., Ekrek S., Durak A.T., Abbak M., Çevik Ö., Kaşkatepe B., Küçükgüzel İ., Küçükgüzel G., Novel 2,6-disubstituted pyridine hydrazones: synthesis, anticancer activity, docking studies and effects on caspase-3-mediated apoptosis, J. Mol. Struct., 1223(2021) 128962-128969.
  • [22] Şenkardeş S., Han M.İ., Kulabaş N., Abbak M., Çevik Ö., Küçükgüzel İ., Küçükgüzel G., Synthesis, molecular docking and evaluation of novel sulfonyl hydrazones as anticancer agents and COX-2 ınhibitors, Mol. Divers., 24(3) (2020) 673-689.
  • [23] Şenkardeş S., Kaushik-Basu N., Durmaz I., Manvar D., Basu A., Atalay R., Kucukguzel, S.G., Synthesis of novel diflunisal hydrazide-hydrazones as anti-hepatitis c virus agents and hepatocellular carcinoma ınhibitors, Eur. J. Med. Chem., 108(27) (2016) 301-308.
  • [24] Aktar B.S.K., Sıcak Y., Tok T.T., Oruc-Emre E.E., Yağlıoğlu A.Ş., Iyidoğan A K., Öztürk M., Demirtaş I., Designing heterocyclic chalcones, benzoyl/sulfonyl hydrazones: An insight into their biological activities and molecular docking study, J. Mol. Struct., 1211 (2020) 128059.
  • [25] Karaman N., Sıcak Y., Taşkın-Tok T., Öztürk M., Karaküçük-İyidoğan A., Dikmen M., Oruç-Emre E.E., New piperidine-hydrazone derivatives: Synthesis, biological evaluations and molecular docking studies as AChE and BChE inhibitors, Eur. J. Med. Chem., 124 (2016) 270-283.
  • [26] Çakmak R., Başaran E., Şentürk M., Synthesis, characterization, and biological evaluation of some novel Schiff bases as potential metabolic enzyme inhibitors, Arch. Pharm., 355(4) (2022) 2100430.
  • [27] Qin H.L., Zhang Z.W., Ravindar L., Rakesh K.P., Antibacterial activities with the structure-activity relationship of coumarin derivatives, Eur. J. Med. Chem., 207 (2020) 112832.
  • [28] Çınar E., Başaran E., Erdoğan Ö., Çakmak R., Boğa M., Çevik Ö., Heterocyclic Schiff base derivatives containing pyrazolone moiety: Synthesis, characterization, and in vitro biological studies, J. Chin. Chem. Soc., 68(12) (2021) 2355-2367.
  • [29] Çakmak R., Başaran E., Boğa M., Erdoğan Ö., Çınar E., Çevik Ö., Schiff base derivatives of 4-aminoantipyrine as promising molecules: synthesis, structural characterization and biological activities, Russ. J. Bioorganic Chem., 48(2) (2022).
  • [30] Paşa S., Erdogan Ö., Cevik Ö., Design, synthesis and investigation of procaine based new Pd complexes as DNA methyltransferase inhibitor on gastric cancer cells, Inorg. Chem. Commun., 132 (2021) 108846.
  • [31] Sıcak Y., Investigation of antioxidant, anticholinesterase inhibitory, tyrosinase inhibitory and urease inhibitory activities of some hydrazone derivatives, Turk. J. Life Sci., 2(2) (2017) 165-170.
  • [32] Bozkurt E., Sıcak Y., Oruç-Emre E.E., Iyidoğan A.K., Öztürk, M., Design and bioevaluation of novel hydrazide-hydrazones derived from 4-acetyl-N-substituted benzenesulfonamide, Russ. J. Bioorganic Chem., 46(5) (2020) 702-714.
  • [33] Sıcak Y., Oruç‐Emre E.E., Öztürk M., Taşkın‐Tok T., Karaküçük‐Iyidoğan A., Novel fluorine‐containing chiral hydrazide‐hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, and in silico studies, Chirality., 31(8) (2019) 603-615.
  • [34] Aktar B.S.K., Sıcak Y., Tatar G., Emre E.E., Synthesis of benzoyl hydrazones having 4-hydroxy-3, 5-dimethoxy phenyl ring, theirbiological activities, and molecular modeling studies on enzyme inhibition activities, Turk. J. Chem., 46(1) (2022) 236-252.

Year 2022, Volume 43, Issue 3, 437 - 442, 30.09.2022
https://doi.org/10.17776/csj.1099217

Abstract

References

  • [1] De Silva D.D., Rapior S., Fons F., Bahkali A.H., Hyde, K.D., Medicinal mushrooms in supportive cancer therapies: an approach to anti-cancer effects and putative mechanisms of action, Fungal Divers., 55(1) (2012) 1-35.
  • [2] Atmaca H., Oğuz F., Ilhan S., Drug delivery systems for cancer treatment: a review of marine-derived polysaccharides, Curr. Pharm. Des., (2022).
  • [3] Küpeli Akkol E., Genç Y., Karpuz B., Sobarzo-Sánchez E., Capasso, R., Coumarins and coumarin-related compounds in pharmacotherapy of cancer, Cancers., 12(7) (2020) 1959.
  • [4] Kashyap D., Garg V.K., Sandberg E.N., Goel N., Bishayee, A., Oncogenic and tumor suppressive components of the cell cycle in breast cancer progression and prognosis, Pharmaceutics., 13(4) (2021) 569.
  • [5] Luna J.I., Grossenbacher S.K., Murphy W.J., Canter, R. J., Targeting cancer stem cells with natural killer cell immunotherapy, Expert Opin. Biol. Ther., 17(3) (2017) 313-324.
  • [6] Weiss, T., Weller M., Roth, P., Immunological effects of chemotherapy and radiotherapy against brain tumors, Expert Rev. Anticancer Ther., 16(10) (2016) 1087-1094.
  • [7] Scarpa E.S., Fabrizio G., Di Girolamo M., A role of intracellular mono‐ADP‐ribosylation in cancer biology, The FEBS J., 280(15) (2013) 3551-3562.
  • [8] Mansoori B., Mohammadi A., Davudian S., Shirjang S., Baradaran, B., The different mechanisms of cancer drug resistance: a brief review, Adv. Pharm. Bull., 7(3) (2017) 339-348.
  • [9] Longley D.B., Johnston P.G., Molecular mechanisms of drug resistance, J. Pathol., 205(2) (2005) 275-292.
  • [10] Goodman L.S., Wintrobe M.M., Dameshek W., Goodman M.J., Gilman A., McLennan M.T., Nitrogen mustard therapy: Use of methyl-bis (beta-chloroethyl) amine hydrochloride and tris (beta-chloroethyl) amine hydrochloride for hodgkin's disease, lymphosarcoma, leukemia and certain allied and miscellaneous disorders, JAMA, 132(3) (1946) 126-132.
  • [11] Barinaga M., From bench top to bedside, Sci., 278(5340) (1997) 1036-1039.
  • [12] Calabresi P., Welch A.D., Chemotherapy of neoplastic diseases, Annu. Rev. Med., 13(1) (1962) 147-202.
  • [13] Carter S.K., Slavik M., Chemotherapy of cancer, Annu. Rev. Pharmacol., 14(1) (1974) 157-179.
  • [14] Sung H., Ferlay J., Siegel R.L., Laversanne M., Soerjomataram I., Jemal A., Bray F., Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries, CA cancer J. Clin., 71(3) (2021) 209-249.
  • [15] Cancer, UK, How Chemotherapy Drugs Work. Available at: https://www.cancer.org/treatment/treatments-and-side-effects/treatment-types/chemotherapy/how-chemotherapy-drugs-work.html, 2021 (accessed 28 Mar 2022).
  • [16] Al-Mulla A., A review: biological importance of heterocyclic compounds, Der Pharma Chem., 9(13) (2017) 141-147.
  • [17] Çakmak R., Başaran E., Kaya S., Erkan S., Synthesis, spectral characterization, chemical reactivity and anticancer behaviors of some novel hydrazone derivatives: Experimental and theoretical insights, J. Mol. Struct., 1253 (2022) 132224.
  • [18] Başaran E., Haşimi N., Çakmak R., Çınar E., Synthesis, structural characterization, and biological evaluation of some hydrazone compounds as potential antioxidant agents, Russ. J. Bioorganic Chem., 48(1) (2022) 143-152.
  • [19] Tabbiche A., Bouchama A., Chafai N., Zaidi F., Chiter C., Yahiaoui M., Abiza A., New bis hydrazone: synthesis, x-ray crystal structure, DFT computations, conformational study and in silico study of the ınhibition activity of SARS-CoV-2, J. Mol. Struct., 1261 (2022) 132865.
  • [20] Aydin S., Kaushik-Basu N., Arora P., Basu A., Nichols D.B., Talele T.T., Akkurt M., Çelik I., Büyükgungör O., Kucukguzel Ş.G., Microwave assisted synthesis of some novel flurbiprofen hydrazide-hydrazones as anti-hcv ns5b and anticancer agents, Marmara Pharm. J., 17(1) (2013) 26-34.
  • [21] Şenkardeş S., Türe A., Ekrek S., Durak A.T., Abbak M., Çevik Ö., Kaşkatepe B., Küçükgüzel İ., Küçükgüzel G., Novel 2,6-disubstituted pyridine hydrazones: synthesis, anticancer activity, docking studies and effects on caspase-3-mediated apoptosis, J. Mol. Struct., 1223(2021) 128962-128969.
  • [22] Şenkardeş S., Han M.İ., Kulabaş N., Abbak M., Çevik Ö., Küçükgüzel İ., Küçükgüzel G., Synthesis, molecular docking and evaluation of novel sulfonyl hydrazones as anticancer agents and COX-2 ınhibitors, Mol. Divers., 24(3) (2020) 673-689.
  • [23] Şenkardeş S., Kaushik-Basu N., Durmaz I., Manvar D., Basu A., Atalay R., Kucukguzel, S.G., Synthesis of novel diflunisal hydrazide-hydrazones as anti-hepatitis c virus agents and hepatocellular carcinoma ınhibitors, Eur. J. Med. Chem., 108(27) (2016) 301-308.
  • [24] Aktar B.S.K., Sıcak Y., Tok T.T., Oruc-Emre E.E., Yağlıoğlu A.Ş., Iyidoğan A K., Öztürk M., Demirtaş I., Designing heterocyclic chalcones, benzoyl/sulfonyl hydrazones: An insight into their biological activities and molecular docking study, J. Mol. Struct., 1211 (2020) 128059.
  • [25] Karaman N., Sıcak Y., Taşkın-Tok T., Öztürk M., Karaküçük-İyidoğan A., Dikmen M., Oruç-Emre E.E., New piperidine-hydrazone derivatives: Synthesis, biological evaluations and molecular docking studies as AChE and BChE inhibitors, Eur. J. Med. Chem., 124 (2016) 270-283.
  • [26] Çakmak R., Başaran E., Şentürk M., Synthesis, characterization, and biological evaluation of some novel Schiff bases as potential metabolic enzyme inhibitors, Arch. Pharm., 355(4) (2022) 2100430.
  • [27] Qin H.L., Zhang Z.W., Ravindar L., Rakesh K.P., Antibacterial activities with the structure-activity relationship of coumarin derivatives, Eur. J. Med. Chem., 207 (2020) 112832.
  • [28] Çınar E., Başaran E., Erdoğan Ö., Çakmak R., Boğa M., Çevik Ö., Heterocyclic Schiff base derivatives containing pyrazolone moiety: Synthesis, characterization, and in vitro biological studies, J. Chin. Chem. Soc., 68(12) (2021) 2355-2367.
  • [29] Çakmak R., Başaran E., Boğa M., Erdoğan Ö., Çınar E., Çevik Ö., Schiff base derivatives of 4-aminoantipyrine as promising molecules: synthesis, structural characterization and biological activities, Russ. J. Bioorganic Chem., 48(2) (2022).
  • [30] Paşa S., Erdogan Ö., Cevik Ö., Design, synthesis and investigation of procaine based new Pd complexes as DNA methyltransferase inhibitor on gastric cancer cells, Inorg. Chem. Commun., 132 (2021) 108846.
  • [31] Sıcak Y., Investigation of antioxidant, anticholinesterase inhibitory, tyrosinase inhibitory and urease inhibitory activities of some hydrazone derivatives, Turk. J. Life Sci., 2(2) (2017) 165-170.
  • [32] Bozkurt E., Sıcak Y., Oruç-Emre E.E., Iyidoğan A.K., Öztürk, M., Design and bioevaluation of novel hydrazide-hydrazones derived from 4-acetyl-N-substituted benzenesulfonamide, Russ. J. Bioorganic Chem., 46(5) (2020) 702-714.
  • [33] Sıcak Y., Oruç‐Emre E.E., Öztürk M., Taşkın‐Tok T., Karaküçük‐Iyidoğan A., Novel fluorine‐containing chiral hydrazide‐hydrazones: Design, synthesis, structural elucidation, antioxidant and anticholinesterase activity, and in silico studies, Chirality., 31(8) (2019) 603-615.
  • [34] Aktar B.S.K., Sıcak Y., Tatar G., Emre E.E., Synthesis of benzoyl hydrazones having 4-hydroxy-3, 5-dimethoxy phenyl ring, theirbiological activities, and molecular modeling studies on enzyme inhibition activities, Turk. J. Chem., 46(1) (2022) 236-252.

Details

Primary Language English
Subjects Chemistry, Multidisciplinary
Journal Section Natural Sciences
Authors

Eyüp BAŞARAN> (Primary Author)
BATMAN ÜNİVERSİTESİ/TEKNİK BİLİMLER MESLEK YÜKSEKOKULU/KİMYA VE KİMYASAL İŞLEME TEKNOLOJİLERİ BÖLÜMÜ
0000-0002-7840-5919
Türkiye


Reşit ÇAKMAK>
BATMAN ÜNİVERSİTESİ
0000-0003-0401-7419
Türkiye


Ercan ÇINAR>
BATMAN ÜNİVERSİTESİ
0000-0003-0419-7798
Türkiye


Ozge CEVİK>
AYDIN ADNAN MENDERES ÜNİVERSİTESİ
0000-0002-9325-3757
Türkiye

Publication Date September 30, 2022
Application Date April 6, 2022
Acceptance Date September 7, 2022
Published in Issue Year 2022, Volume 43, Issue 3

Cite

APA Başaran, E. , Çakmak, R. , Çınar, E. & Cevik, O. (2022). Some Heterocyclic Hydrazone Compounds: Synthesis, Spectral Characterization and Anticancer Activity Study . Cumhuriyet Science Journal , 43 (3) , 437-442 . DOI: 10.17776/csj.1099217