Green Synthesis and Anticancer Evaluation of Novel Chrysin Hydrazone Derivatives

References

• L. Yount, Cancer (San Diego: Lucent Books, 1999).
   Google Scholar
• F. Bray, A. Jemal, N. Grey, J. Ferlay, and D. Forman, “Global Cancer Transitions according to the Human Development Index (2008–2030): A Population-Based Study,” The Lancet Oncology 13, no. 8 (2012): 790–801.
   PubMed Web of Science ®Google Scholar
• C. Stein, and G. Colditz, “Modifiable Risk Factors for Cancer,” British Journal of Cancer 90, no. 2 (2004): 299–303.
   PubMed Web of Science ®Google Scholar
• K. N. Moore, A. A. Secord, M. A. Geller, D. S. Miller, N. Cloven, G. F. Fleming, A. E. Wahner Hendrickson, M. Azodi, P. DiSilvestro, A. M. Oza, et al. “Niraparib Monotherapy for Late-Line Treatment of Ovarian Cancer (QUADRA): A Multicentre, Open-Label, Single-Arm, Phase 2 Trial,” The Lancet. Oncology 20, no. 5 (2019): 636–48.
   PubMed Web of Science ®Google Scholar
• S. De Placido, C. Gallo, M. De Laurentiis, G. Bisagni, G. Arpino, M. G. Sarobba, F. Riccardi, A. Russo, L. Del Mastro, A. A. Cogoni, et al. “Adjuvant Anastrozole versus Exemestane versus Letrozole, Upfront or after 2 Years of Tamoxifen, in Endocrine-Sensitive Breast Cancer (FATA-GIM3): A Randomised, Phase 3 Trial,” The Lancet Oncology 19, no. 4 (2018): 474–85.
   PubMed Web of Science ®Google Scholar
• J.-C. Soria, Y.-L. Wu, K. Nakagawa, S.-W. Kim, J.-J. Yang, M.-J. Ahn, J. Wang, J. C.-H. Yang, Y. Lu, S. Atagi, et al. “Gefitinib plus Chemotherapy versus Placebo plus Chemotherapy in EGFR-Mutation-Positive Non-Small-Cell Lung Cancer after Progression on First-Line Gefitinib (IMPRESS): A Phase 3 Randomised Trial,” The Lancet Oncology 16, no. 8 (2015): 990–8.
   PubMed Web of Science ®Google Scholar
• J. C.-H. Yang, Y.-L. Wu, M. Schuler, M. Sebastian, S. Popat, N. Yamamoto, C. Zhou, C.-P. Hu, K. O’Byrne, J. Feng, et al. “Afatinib versus Cisplatin-Based Chemotherapy for EGFR Mutation-Positive Lung Adenocarcinoma (LUX-Lung 3 and LUX-Lung 6): Analysis of Overall Survival Data from Two Randomised, Phase 3 Trials,” The Lancet Oncology 16, no. 2 (2015): 141–51.
   PubMed Web of Science ®Google Scholar
• Z. Xiao, S. L. Morris‐Natschke, and K. H. Lee, “Strategies for the Optimization of Natural Leads to Anticancer Drugs or Drug Candidates,” Medicinal Research Reviews 36, no. 1 (2016): 32–91.
   PubMed Web of Science ®Google Scholar
• A. Ghasemzadeh, and N. Ghasemzadeh, “Flavonoids and Phenolic Acids: Role and Biochemical Activity in Plants and Human,” Journal of Medicinal Plants Research 5, no. 31 (2011): 6697–703.
   Web of Science ®Google Scholar
• J.M. Awika, “Sorghum Flavonoids: Unusual Compounds with Promising Implications for Health,” in Advances in Cereal Science: Implications to Food Processing and Health Promotion (Washington, DC: ACS Publications, 2011), 171–200.
   Google Scholar
• A. Bertrand, and D. Olivier, “Acylated Flavone Glucosides: Synthesis, Conformational Investigation and Complexation Propertie,” Helvetica Chimica Acta 82, no. 12 (1999): 2201–12.
   Web of Science ®Google Scholar
• C. A. Rice-Evans, L. Packer, Flavonoids in Health and Disease (Boca Raton: CRC Press, 2003).
   Google Scholar
• P. Zanoli, R. Avallone, and M. Baraldi, “Behavioral Characterisation of the Flavonoids Apigenin and Chrysin,” Fitoterapia 71 (2000): S117–S123.
   PubMed Web of Science ®Google Scholar
• E. C. Chan, P. Pannangpetch, and O. L. Woodman, “Relaxation to Flavones and Flavonols in Rat Isolated Thoracic Aorta: Mechanism of Action and Structure-Activity Relationships,” Journal of Cardiovascular Pharmacology 35, no. 2 (2000): 326–33.
   PubMed Web of Science ®Google Scholar
• J. Lee, Y. Kim, C. Lee, H. Lee, and S. Han, “Use of Flavones, Coumarins and Related Compounds to Treat Infections,” Saengyak Hakhoe Chi 30 (1999): 34–9.
   Google Scholar
• J.-S. Shin, K.-S. Kim, M.-B. Kim, J.-H. Jeong, and B.-K. Kim, “Synthesis and Hypoglycemic Effect of Chrysin Derivatives,” Bioorganic & Medicinal Chemistry Letters 9, no. 6 (1999): 869–74.
   PubMed Web of Science ®Google Scholar
• S. C. Joshi, L. Strauss, S. Mäkelä, and R. Santti2, “Inhibition of 17beta-Estradiol Formation by Isoflavonoids and Flavonoids in Cultured JEG-3 Cells: Search for Aromatase-Targeting Dietary Compounds,” Journal of Medicinal Food 2, no. 3-4 (1999): 235–8.
   PubMedGoogle Scholar
• I. Kubo, I. Kinst-Hori, S. K. Chaudhuri, Y. Kubo, Y. Sánchez, and T. Ogura, “Flavonols from Heterotheca Inuloides: Tyrosinase Inhibitory Activity and Structural Criteria,” Bioorganic & Medicinal Chemistry 8, no. 7 (2000): 1749–55.
   PubMed Web of Science ®Google Scholar
• S. Habtemariam, “Flavonoids as Inhibitors or Enhancers of the Cytotoxicity of Tumor Necrosis Factor-Alpha in L-929 Tumor Cells,” Journal of Natural Products 60, no. 8 (1997): 775–8.
   PubMed Web of Science ®Google Scholar
• X. Zheng, W.-D. Meng, Y.-Y. Xu, J.-G. Cao, and F.-L. Qing, “Synthesis and Anticancer Effect of Chrysin Derivatives,” Bioorganic & Medicinal Chemistry Letters 13, no. 5 (2003): 881–4.
   PubMed Web of Science ®Google Scholar
• M. D. Altıntop, A. Özdemir, G. Turan-Zitouni, S. Ilgın, Ö. Atlı, G. İşcan, and Z. A. Kaplancıklı, “Synthesis and Biological Evaluation of Some Hydrazone Derivatives as New Anticandidal and Anticancer Agents,” European Journal of Medicinal Chemistry 58 (2012): 299–307.
   PubMed Web of Science ®Google Scholar
• V. T. Angelova, N. G. Vassilev, B. Nikolova-Mladenova, J. Vitas, R. Malbaša, G. Momekov, M. Djukic, and L. Saso, “Antiproliferative and Antioxidative Effects of Novel Hydrazone Derivatives Bearing Coumarin and Chromene Moiety,” Medicinal Chemistry Research 25, no. 9 (2016): 2082–92.
   Web of Science ®Google Scholar
• Z. A. Kaplancıklı, L. Yurttaş, A. Özdemir, G. Turan-Zitouni, G. A. Çiftçi, ŞU. Yıldırım, and U. A. Mohsen, “Synthesis and Antiproliferative Activity of New 1, 5-Disubstituted Tetrazoles Bearing Hydrazone Moiety,” Medicinal Chemistry Research 23, no. 2 (2014): 1067–75.
   Web of Science ®Google Scholar
• S. M. Gomha, T. A. Salah, and A. O. Abdelhamid, “Synthesis, Characterization, and Pharmacological Evaluation of Some Novel Thiadiazoles and Thiazoles Incorporating Pyrazole Moiety as Anticancer Agents,” Monatshefte für Chemie - Chemical Monthly 146, no. 1 (2015): 149–58.
   Google Scholar
• S. M. Riyadh, S. M. Gomha, E. A. Mahmmoud, and M. M. Elaasser, “Synthesis and Anticancer Activities of Thiazoles, 1, 3-Thiazines, and Thiazolidine Using Chitosan-Grafted-Poly (Vinylpyridine) as Basic Catalyst,” Heterocycles 91, no. 6 (2015): 1227–43.
   Web of Science ®Google Scholar
• S. M. Gomha, S. M. Riyadh, E. A. Mahmmoud, and M. M. Elaasser, “Synthesis and Anticancer Activity of Arylazothiazoles and 1, 3, 4-Thiadiazoles Using Chitosan-Grafted-Poly (4-Vinylpyridine) as a Novel Copolymer Basic Catalyst,” Chemistry of Heterocyclic Compounds 51, no. 11–12 (2015): 1030–8.
   Web of Science ®Google Scholar
• S. M. Gomha, N. A. Kheder, M. R. Abdelaziz, Y. N. Mabkhot, and A. M. Alhajoj, “A Facile Synthesis and Anticancer Activity of Some Novel Thiazoles Carrying 1,3,4-Thiadiazole Moiety,” Chemistry Central Journal 11, no. 1 (2017): 1–9.
   PubMedGoogle Scholar
• A. O. Abdelhamid, S. M. Gomha, N. A. Abdelriheem, and S. M. Kandeel, “Synthesis of New 3-Heteroarylindoles as Potential Anticancer Agents,” Molecules 21, no. 7 (2016): 929.
   PubMed Web of Science ®Google Scholar
• S. M. Gomha, Z. A. Muhammad, H. M. Abdel-Aziz, I. K. Matar, and A. A. El-Sayed, “Green Synthesis, Molecular Docking and Anticancer Activity of Novel 1, 4-Dihydropyridine-3, 5-Dicarbohydrazones under Grind-Stone Chemistry,” Green Chemistry Letters and Reviews 13, 1 (2020): 6–17. no
   Web of Science ®Google Scholar
• A. Gürsoy, N. Terzioglu, and G. Ötük, “Synthesis of Some New Hydrazide-Hydrazones, Thiosemicarbazides and Thiazolidinones as Possible Antimicrobials,” European Journal of Medicinal Chemistry 32, no. 9 (1997): 753–7.
   Web of Science ®Google Scholar
• R. Narang, B. Narasimhan, and S. Sharma, “A Review on Biological Activities and Chemical Synthesis of Hydrazide Derivatives,” Current Medicinal Chemistry 19, no. 4 (2012): 569–612.
   PubMed Web of Science ®Google Scholar
• B. K. Kaymakçıoğlu, and S. Rollas, “Synthesis, Characterization and Evaluation of Antituberculosis Activity of Some Hydrazones,” Il Farmaco 57, no. 7 (2002): 595–9.
   PubMedGoogle Scholar
• N. Terzioglu, and A. Gürsoy, “Synthesis and Anticancer Evaluation of Some New Hydrazone Derivatives of 2, 6-Dimethylimidazo [2,1-b][1,3,4] Thiadiazole-5-Carbohydrazide,” European Journal of Medicinal Chemistry 38, no. 7–8 (2003): 781–6.
   PubMed Web of Science ®Google Scholar
• V. Onnis, M. T. Cocco, R. Fadda, and C. Congiu, “Synthesis and Evaluation of Anticancer Activity of 2-Arylamino-6-Trifluoromethyl-3-(Hydrazonocarbonyl)pyridines,” Bioorganic & Medicinal Chemistry 17, no. 17 (2009): 6158–65.
   PubMed Web of Science ®Google Scholar
• A. Ayati, S. Moghimi, S. Salarinejad, M. Safavi, B. Pouramiri, and A. Foroumadi, “A Review on Progression of Epidermal Growth Factor Receptor (EGFR) Inhibitors as an Efficient Approach in Cancer Targeted Therapy,” Bioorganic Chemistry 99 (2020): 103811.
   PubMed Web of Science ®Google Scholar
• B. Pouramiri, E. T. Kermani, and M. Khaleghi, “One-Pot, Three-Component Synthesis and in Vitro Antibacterial Evaluation of Novel 3-amino-N-Benzyl-1-Aryl-1H-Benzo [f] Chromene-2-Carboxamide Derivatives,” Journal of the Iranian Chemical Society 14, no. 11 (2017): 2331–7.
   Web of Science ®Google Scholar
• B. Pouramiri, S. Moghimi, M. Mahdavi, H. Nadri, A. Moradi, E. Tavakolinejad‐Kermani, L. Firoozpour, A. Asadipour, and A. Foroumadi, “Synthesis and Anticholinesterase Activity of New Substituted Benzo[d]oxazole-Based Derivatives,” Chemical Biology & Drug Design 89, no. 5 (2017): 783–9.
   PubMed Web of Science ®Google Scholar
• M. J. Earle, S. P. Katdare, and K. R. Seddon, “Paradigm Confirmed: The First Use of Ionic Liquids to Dramatically Influence the Outcome of Chemical Reactions,” Organic Letters 6, no. 5 (2004): 707–10.
   PubMed Web of Science ®Google Scholar
• E. Mizushima, T. Hayashi, and M. Tanaka, “Palladium-Catalysed Carbonylation of Aryl Halides in Ionic Liquid Media: High Catalyst Stability and Significant Rate-Enhancement in Alkoxycarbonylation,” Green Chemistry 3, no. 2 (2001): 76–9.
   Web of Science ®Google Scholar
• R. Vijayaraghavan, and D. R. MacFarlane, “Charge Transfer Polymerization in Ionic Liquids,” Australian Journal of Chemistry 57, no. 2 (2004): 129–33.
   Web of Science ®Google Scholar
• Y. Chauvin, L. Mussmann, and H. Olivier, “A Novel Class of Versatile Solvents for Two‐Phase Catalysis: Hydrogenation, Isomerization, and Hydroformylation of Alkenes Catalyzed by Rhodium Complexes in Liquid 1, 3‐Dialkylimidazolium Salts,” Angewandte Chemie International Edition in English 34, no. 2324 (1996): 2698–700.
   Google Scholar
• M. Johansson, A. A. Lindén, and J.-E. Bäckvall, “Osmium-Catalyzed Dihydroxylation of Alkenes by H2O2 in Room Temperature Ionic Liquid co-Catalyzed by VO(Acac)2 or MeReO3,” Journal of Organometallic Chemistry 690, no. 15 (2005): 3614–9.
   Web of Science ®Google Scholar
• J. S. Wilkes, “A Short History of Ionic Liquids—From Molten Salts to Neoteric Solvents,” Green Chemistry 4, no. 2 (2002): 73–80.
   Web of Science ®Google Scholar
• M. Raeiszadeh, M. Esmaeili-Tarzi, K. Bahrampour-Juybari, S. N. Nematollahi-Mahani, A. Pardakhty, M. H. Nematollahi, M. Mehrabani, and M. Mehrabani, “Evaluation the Effect of Myrtus Communis L. extract on Several Underlying Mechanisms Involved in Wound Healing: An in Vitro Study,” South African Journal of Botany 118 (2018): 144–50.
   Web of Science ®Google Scholar
• M. Mehrabani, M. H. Nematollahi, M. E. Tarzi, K. B. Juybari, M. Abolhassani, A. M. Sharifi, H. Paseban, M. Saravani, and S. Mirzamohammadi, “Protective Effect of Hydralazine on a Cellular Model of Parkinson’s Disease: A Possible Role of Hypoxia-Inducible Factor (HIF)-1α,” Biochemistry and Cell Biology = Biochimie et Biologie Cellulaire 98, no. 3 (2020): 405–14.
   PubMedGoogle Scholar
• S. Rollas, and S. G. Küçükgüzel, “Biological Activities of Hydrazone Derivatives,” Molecules (Basel, Switzerland) 12, no. 8 (2007): 1910–39.
   PubMed Web of Science ®Google Scholar
• M. Bingul, O. Tan, C. R. Gardner, S. K. Sutton, G. M. Arndt, G. M. Marshall, B. B. Cheung, N. Kumar, and D. S. Black, “Synthesis, Characterization and Anticancer Activity of Hydrazide Derivatives Incorporating a Quinoline Moiety,” Molecules 21, no. 7 (2016): 916.
   PubMed Web of Science ®Google Scholar
• A. El-Faham, M. Farooq, S. N. Khattab, N. Abutaha, M. A. Wadaan, H. A. Ghabbour, and H.-K. Fun, “Synthesis, Characterization, and Anti-Cancer Activity of Some New N′-(2-Oxoindolin-3-ylidene)-2-Propylpentane Hydrazide-Hydrazones Derivatives,” Molecules (Basel, Switzerland) 20, no. 8 (2015): 14638–55.
   PubMed Web of Science ®Google Scholar
• T. Nasr, S. Bondock, and M. Youns, “Anticancer Activity of New Coumarin Substituted hydrazide-hydrazone derivatives,” European Journal of Medicinal Chemistry 76 (2014): 539–48.
   PubMed Web of Science ®Google Scholar
• M. T. Abdel‐Aal, W. A. El‐Sayed, and E. S. H. El‐Ashry, “Synthesis and Antiviral Evaluation of Some Sugar Arylglycinoylhydrazones and Their Oxadiazoline Derivatives,” Archiv der Pharmazie 339, no. 12 (2006): 656–63.
   PubMed Web of Science ®Google Scholar
• P. Cozzini, G. E. Kellogg, F. Spyrakis, D. J. Abraham, G. Costantino, A. Emerson, F. Fanelli, H. Gohlke, L. A. Kuhn, G. M. Morris, et al. “Target Flexibility: An Emerging Consideration in Drug Discovery and Design,” Journal of Medicinal Chemistry 51, no. 20 (2008): 6237–55.
   PubMed Web of Science ®Google Scholar
• M. O. Puskullu, H. Shirinzadeh, M. Nenni, H. Gurer-Orhan, and S. Suzen, “Synthesis and Evaluation of Antioxidant Activity of New Quinoline-2-Carbaldehyde Hydrazone Derivatives: Bioisosteric Melatonin Analogues,” Journal of Enzyme Inhibition and Medicinal Chemistry 31, no. 1 (2016): 121–5.
   PubMed Web of Science ®Google Scholar