Exploring 3-Benzyloxyflavones as new lead cholinesterase inhibitors: synthesis, structure–activity relationship and molecular modelling simulations

References

• Agbo, E. N., Gildenhuys, S., & Mphahlele, M. J. (2019). Inhibitory effects of novel 7-substituted 6-iodo-3-o-flavonol glycosides against cholinesterases and β-secretase activities, and evaluation for potential antioxidant properties. Molecules, 24(19), 3500–3553. https://doi.org/https://doi.org/10.3390/molecules24193500
   Web of Science ®Google Scholar
• Anand, P., & Singh, B. (2013). Flavonoids as lead compounds modulating the enzyme targets in Alzheimer’s disease. Medicinal Chemistry Research, 22(7), 3061–3075. https://doi.org/https://doi.org/10.1007/s00044-012-0353-y
   Web of Science ®Google Scholar
• Asghar, A., Yousuf, M., Fareed, G., Nazir, R., Hassan, A., Maalik, A., Noor, T., Iqbal, N., & Rasheed, L. (2020). Synthesis, acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) activities, and molecular docking studies of a novel compound based on combination of flurbiprofen and isoniazide. RSC Advances, 10(33), 19346–19352. https://doi.org/https://doi.org/10.1039/D0RA02339F
   PubMed Web of Science ®Google Scholar
• Bajda, M., Guzior, N., Ignasik, M., & Malawska, B. (2011). Multi-target-directed ligands in Alzheimer's disease treatment. Current Medicinal Chemistry, 18(32), 4949–4975. https://doi.org/https://doi.org/10.2174/092986711797535245
   PubMed Web of Science ®Google Scholar
• Barai, P., Raval, N., Acharya, S., Borisa, A., Bhatt, H., & Acharya, N. (2019). Neuroprotective effects of bergenin in Alzheimer’s disease: Investigation through molecular docking, in vitro and in vivo studies. Behavioural Brain Research, 356, 18–40. https://doi.org/https://doi.org/10.1016/j.bbr.2018.08.010
   PubMed Web of Science ®Google Scholar
• Bhatt, D., Soni, R., Sharma, G. K., & Dashora, A. (2016). Synthesis and pharmacological activities of flavones: A review. American Journal of Pharmaceutical Research, 6(02), 4345.
   Google Scholar
• Bozdag-Dundar, O., Ceylan-Unlusoy, M., Altanlar, N., & Ertan, R. (2005). Synthesis and biological activity of some new flavone derivatives. Arzneimittel-Forschung, 55(2), 102–106. https://doi.org/https://doi.org/10.1055/s-0031-1296830
   PubMed Web of Science ®Google Scholar
• Cavdar, H., Senturk, M., Guney, M., Durdagi, S., Kayik, G., Supuran, C. T., & Ekinci, D. (2019). Inhibition of acetylcholinesterase and butyrylcholinesterase with uracil derivatives: Kinetic and computational studies. Journal of Enzyme Inhibition and Medicinal Chemistry, 34(1), 429–437. https://doi.org/https://doi.org/10.1080/14756366.2018.1543288
   PubMed Web of Science ®Google Scholar
• Chen, Y., Lin, H., Yang, H., Tan, R., Bian, Y., Fu, T., Li, W., Wu, L., Pei, Y., & Sun, H. (2017). Discovery of new acetylcholinesterase and butyrylcholinesterase inhibitors through structure-based virtual screening. RSC Advances, 7(6), 3429–3438. https://doi.org/https://doi.org/10.1039/C6RA25887E
   Web of Science ®Google Scholar
• Daglia, M. (2012). Polyphenols as antimicrobial agents. Current Opinion in Biotechnology, 23(2), 174–181. https://doi.org/https://doi.org/10.1016/j.copbio.2011.08.007
   PubMed Web of Science ®Google Scholar
• Díaz, J. E., Martinez, D. C., López, L. V., Mendez, G. M., Vera, R., & Loaiza, A. E. (2017). Synthesis and in vitro antiproliferative activity of flavone and 6-hydroxyflavone oxime ethers derivatives. Journal of the Brazilian Chemical Society, 29(1), 177–184. https://doi.org/https://doi.org/10.21577/0103-5053.20170128
   Web of Science ®Google Scholar
• Dymarska, M., Janeczko, T., & Kostrzewa-Susłow, E. (2018). Glycosylation of 3-hydroxyflavone, 3-methoxyflavone, quercetin and baicalein in fungal cultures of the genus Isaria. Molecules, 23(10), 2477. https://doi.org/https://doi.org/10.3390/molecules23102477
   Web of Science ®Google Scholar
• Faraji, L., Nadri, H., Moradi, A., Bukhari, S. N. A., Pakseresht, B., Moghadam, F. H., Moghimi, S., Abdollahi, M., Khoobi, M., & Foroumadi, A. (2019). Aminoalkyl-substituted flavonoids: Synthesis, cholinesterase inhibition, β-amyloid aggregation, and neuroprotective study. Medicinal Chemistry Research, 28(7), 974–983. https://doi.org/https://doi.org/10.1007/s00044-019-02350-4
   Web of Science ®Google Scholar
• Genoux, E., Nicolle, E., & Boumendjel, A. (2011). Flavonoids as anticancer agents: Recent progress and state of the art?. Current Organic Chemistry, 15(15), 2608–2615. https://doi.org/https://doi.org/10.2174/138527211796367363
   Web of Science ®Google Scholar
• Graf, B. A., Milbury, P. E., & Blumberg, J. B. (2005). Flavonols, flavones, flavanones, and human health: Epidemiological evidence. Journal of Medicinal Food, 8(3), 281–290. https://doi.org/https://doi.org/10.1089/jmf.2005.8.281
   PubMed Web of Science ®Google Scholar
• Gunduz, S., Goren, A. C., & Ozturk, T. (2012). Facile syntheses of 3-hydroxyflavones. Organic Letters, 14(6), 1576–1579. https://doi.org/https://doi.org/10.1021/ol300310e
   PubMed Web of Science ®Google Scholar
• Gupta, V. K., Mergu, N., & Singh, A. K. (2014). Fluorescent chemosensors for Zn2+ ions based on flavonol derivatives. Sensors and Actuators B: Chemical, 202, 674–682. https://doi.org/https://doi.org/10.1016/j.snb.2014.05.133
   Web of Science ®Google Scholar
• Harborne, J. B., & Williams, C. A. (2000). Advances in flavonoid research since 1992. Phytochemistry, 55(6), 481–504. https://doi.org/https://doi.org/10.1016/S0031-9422(00)00235-1
   PubMed Web of Science ®Google Scholar
• Hostetler, G. L., Ralston, R. A., & Schwartz, S. J. (2017). Flavones: Food sources, bioavailability, metabolism, and bioactivity. Advances in Nutrition (Bethesda, MD), 8(3), 423–435. https://doi.org/https://doi.org/10.3945/an.116.012948
   PubMed Web of Science ®Google Scholar
• Ibrahim, N. S. (2014). Antimicrobial activities of some synthetic flavonoids. IOSR Journal of Applied Chemistry, 7(5), 01–06., & Ahmed, F. https://doi.org/https://doi.org/10.9790/5736-07520106
   Google Scholar
• Imran, S., Taha, M., Ismail, N. H., Kashif, S. M., Rahim, F., Jamil, W., Wahab, H., & Khan, K. M. (2016). Synthesis, in vitro and docking studies of new flavone ethers as α‐glucosidase inhibitors. Chemical Biology & Drug Design, 87(3), 361–373. https://doi.org/https://doi.org/10.1111/cbdd.12666
   PubMed Web of Science ®Google Scholar
• Jin, L., Wang, M. L., Lv, Y., Zeng, X.-Y., Chen, C., Ren, H., Luo, H., & Pan, W. D. (2019). Design and synthesis of flavonoidal ethers and their anti-cancer activity in vitro. Molecules, 24(9), 1749. https://doi.org/https://doi.org/10.3390/molecules24091749
   Web of Science ®Google Scholar
• Kamboj, R. C., Pratibha, P., Kumar, D., Sharma, G., Arora, R., Kumar, P., Kumar, S., Kumar, R., & Kamal, R. (2013). Intramolecular cyclization of photolabile thienylchromenones (I): Synthesis of angular tetracyclic compounds (II). ChemInform, 44(46), no–249. https://doi.org/https://doi.org/10.1002/chin.201346136
   Google Scholar
• Kamlesh, K., Sivakumar, T., & Afroze, A. (2017). Antimicrobial activity of flavone analogues. Journal of Applied Pharmacy, 09 (01), 2. https://doi.org/https://doi.org/10.21065/1920-4159.1000232
   Google Scholar
• Kavitha, P. (2012). Ultrasonic studies on molecular interactions in binary mixtures of sesame oil with organic solvents. Indian Journal of Advances in Chemical Science, 5(12), 148–154.
   Google Scholar
• Khanna, R., Kumar, R., Dalal, A., & Kamboj, R. C. (2015). Absorption and fluorescent studies of 3-hydroxychromones. Journal of Fluorescence, 25(5), 1159–1163. https://doi.org/https://doi.org/10.1007/s10895-015-1623-0
   PubMed Web of Science ®Google Scholar
• Li, X., Lee, M., Chen, G., Zhang, Q., Zheng, S., Wang, G., & Chen, Q.-H. (2017). 3-O-Substituted-3′, 4′, 5′-trimethoxyflavonols: Synthesis and cell-based evaluation as anti-prostate cancer agents. Bioorganic & Medicinal Chemistry, 25(17), 4768–4777. https://doi.org/https://doi.org/10.1016/j.bmc.2017.07.022
   PubMed Web of Science ®Google Scholar
• Liu, H. L., Jiang, W. B., & Xie, M. X. (2010). Flavonoids: Recent advances as anticancer drugs. Recent Patents on anti-Cancer Drug Discovery, 5(2), 152–164. https://doi.org/https://doi.org/10.2174/157489210790936261
   PubMed Web of Science ®Google Scholar
• Loizzo, M. R., Tundis, R., Menichini, F., & Menichini, F. (2008). Natural products and their derivatives as cholinesterase inhibitors in the treatment of neurodegenerative disorders: An update. Current Medicinal Chemistry, 15(12), 1209–1228. https://doi.org/https://doi.org/10.2174/092986708784310422
   PubMed Web of Science ®Google Scholar
• Mahmoud, M. R., Abu El-Azm, F. S., Ali, A. T., & Ali, Y. M. (2017). Synthesis and antimicrobial evaluation of some novel dithiolane, thiophene, coumarin, and 2-pyridone derivatives. Synthetic Communications, 47(17), 1591–1600. https://doi.org/https://doi.org/10.1080/00397911.2017.1336776
   Web of Science ®Google Scholar
• Mathew, B., Parambi, D. G., Mathew, G. E., Uddin, M. S., Inasu, S. T., Kim, H., Marathakam, A., Unnikrishnan, M. K., & Carradori, S. (2019). Emerging therapeutic potentials of dual‐acting MAO and AChE inhibitors in Alzheimer's and Parkinson's diseases. Archiv Der Pharmazie, 352(11), 1900177. https://doi.org/https://doi.org/10.1002/ardp.201900177
   PubMed Web of Science ®Google Scholar
• Mishra, C. B., Kumari, S., Manral, A., Prakash, A., Saini, V., Lynn, A. M., & Tiwari, M. (2017). Design, synthesis, in-silico and biological evaluation of novel donepezil derivatives as multi-target-directed ligands for the treatment of Alzheimer's disease. European Journal of Medicinal Chemistry, 125, 736–750. https://doi.org/https://doi.org/10.1016/j.ejmech.2016.09.057
   PubMed Web of Science ®Google Scholar
• Mishra, B. B., & Tiwari, V. K. (2011). Natural products: An evolving role in future drug discovery. European Journal of Medicinal Chemistry, 46(10), 4769–4807. https://doi.org/https://doi.org/10.1016/j.ejmech.2011.07.057
   PubMed Web of Science ®Google Scholar
• Mphahlele, M. J., Agbo, E. N., & Gildenhuys, S. (2018). Synthesis and evaluation of the 4-substituted 2-hydroxy-5-iodochalcones and their 7-substituted 6-iodoflavonol derivatives for inhibitory effect on cholinesterases and β-secretase. International Journal of Molecular Sciences, 19(12), 4112. https://doi.org/https://doi.org/10.3390/ijms19124112
   Web of Science ®Google Scholar
• Mughal, E. U., Ayaz, M., Hussain, Z., Hasan, A., Sadiq, A., Riaz, M., Malik, A., Hussain, S., & Choudhary, M. I. (2006). Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones. Bioorganic & Medicinal Chemistry, 14(14), 4704–4711. https://doi.org/https://doi.org/10.1016/j.bmc.2006.03.031
   PubMed Web of Science ®Google Scholar
• Mughal, E. U., Javid, A., Sadiq, A., Murtaza, S., Zafar, M. N., Khan, B. A., Sumrra, S. H., Tahir, M. N., & Khan, K. M. (2018). Synthesis, structure-activity relationship and molecular docking studies of 3-O-flavonol glycosides as cholinesterase inhibitors. Bioorganic & Medicinal Chemistry, 26(12), 3696–3706.
   PubMed Web of Science ®Google Scholar
• Mughal, E. U., Sadiq, A., Ashraf, J., Zafar, M. N., Sumrra, S. H., Tariq, R., Mumtaz, A., Javid, A., Khan, B. A., Ali, A., & Javed, C. O. (2019). Flavonols and 4-thioflavonols as potential acetylcholinesterase and butyrylcholinesterase inhibitors: Synthesis, structure-activity relationship and molecular docking studies. Bioorganic Chemistry, 91, 103124https://doi.org/https://doi.org/10.1016/j.bioorg.2019.103124
   PubMed Web of Science ®Google Scholar
• Mughal, E. U., Sadiq, A., Khan, B. A., Zafar, M. N., Ahmed, I., & Zubair, M. (2017). Synthesis, molecular docking studies and biological evaluation of 3-iminoaurones as acetylcholinesterase and butyrylcholinesterase inhibitors. Letters in Drug Design & Discovery, 14(9), 1035–1041. https://doi.org/https://doi.org/10.2174/1570180814666170106123959
   Web of Science ®Google Scholar
• Mughal, E. U., Sadiq, A., Murtaza, S., Rafique, H., Zafar, M. N., Riaz, T., Khan, B. A., Hameed, A., & Khan, K. M. (2017). Synthesis, structure-activity relationship and molecular docking of 3-oxoaurones and 3-thioaurones as acetylcholinesterase and butyrylcholinesterase inhibitors. Bioorganic & Medicinal Chemistry, 25(1), 100–106. https://doi.org/https://doi.org/10.1016/j.bmc.2016.10.016
   PubMed Web of Science ®Google Scholar
• Nhu, D., Hawkins, B. C., & Burns, C. J. (2015). Phase transfer catalysis extends the scope of the Algar–Flynn–Oyamada synthesis of 3-hydroxyflavones. Australian Journal of Chemistry, 68(7), 1102–1107. https://doi.org/https://doi.org/10.1071/CH14620
   Web of Science ®Google Scholar
• Özil, M., Balaydın, H. T., & Şentürk, M. (2019). Synthesis of 5-methyl-2, 4-dihydro-3H-1, 2, 4-triazole-3-one’s aryl Schiff base derivatives and investigation of carbonic anhydrase and cholinesterase (AChE, BuChE) inhibitory properties. Bioorganic Chemistry, 86, 705–713. https://doi.org/https://doi.org/10.1016/j.bioorg.2019.02.045
   PubMed Web of Science ®Google Scholar
• Patel, S., & Shah, U. (2017). Synthesis of flavones from 2-hydroxy acetophenone and aromatic aldehyde derivatives by conventional methods and green chemistry approach. Asian Journal of Pharmaceutical and Clinical Research, 10(2), 403–576. https://doi.org/https://doi.org/10.22159/ajpcr.2017.v10i2.15928
   Google Scholar
• Peres, B., Nasr, R., Zarioh, M., Lecerf, F., Di Pietro, A., Baubichon, H., & Boumendjel, A. (2017). Ferrocene-embedded flavonoids targeting the Achilles heel of multidrug-resistant cancer cells through collateral sensitivity. European Journal of Medicinal Chemistry, 130, 346–353. https://doi.org/https://doi.org/10.1016/j.ejmech.2017.02.064
   PubMed Web of Science ®Google Scholar
• Rampa, A., Bisi, A., Valenti, P., Recanatini, M., Cavalli, A., Andrisano, V., Cavrini, V., Fin, L., Buriani, A., & Giusti, P. (1998). Acetylcholinesterase inhibitors: Synthesis and structure-activity relationships of ω-[N-Methyl-N-(3-alkylcarbamoyloxyphenyl)-methyl] aminoalkoxyheteroaryl derivatives. Journal of Medicinal Chemistry, 41(21), 3976–3986. https://doi.org/https://doi.org/10.1021/jm9810046
   PubMed Web of Science ®Google Scholar
• Rao, M. L., & Kumar, A. (2014). Pd-catalyzed atom-economic couplings of triarylbismuth reagents with 2-bromo-and 2, 6-dibromochromones and synthesis of medicinally important fisetin. Tetrahedron Letters, 55(42), 5764–5770. https://doi.org/https://doi.org/10.1016/j.tetlet.2014.08.081
   Web of Science ®Google Scholar
• Rice-Evans, C. (2001). Flavonoid antioxidants. Curr. Med. Chem, 8(7), 797–807. https://doi.org/https://doi.org/10.2174/0929867013373011
   PubMed Web of Science ®Google Scholar
• Sarbu, L., Bahrin, L., Babii, C., Stefan, M., & Birsa, M. (2019). Synthetic flavonoids with antimicrobial activity: A review. Journal of Applied Microbiology, 127(5), 1282–1290. https://doi.org/https://doi.org/10.1111/jam.14271
   PubMed Web of Science ®Google Scholar
• Sashidhara, K. V., Kumar, M., & Kumar, A. (2012). A novel route to synthesis of flavones from salicylaldehyde and acetophenone derivatives. Tetrahedron Letters, 53(18), 2355–2359. https://doi.org/https://doi.org/10.1016/j.tetlet.2012.02.108
   Web of Science ®Google Scholar
• Saxena, M., & Dubey, R. (2019). Target enzyme in Alzheimer’s disease: Acetylcholinesterase inhibitors. Current Topics in Medicinal Chemistry, 19(4), 264–275. https://doi.org/https://doi.org/10.2174/1568026619666190128125912
   PubMed Web of Science ®Google Scholar
• Shaik, J. B., Palaka, B. K., Penumala, M., Kotapati, K. V., Devineni, S. R., Eadlapalli, S., Darla, M. M., Ampasala, D. R., Vadde, R., & Amooru, G. D. (2016). Synthesis, pharmacological assessment, molecular modeling and in silico studies of fused tricyclic coumarin derivatives as a new family of multifunctional anti-Alzheimer agents. European Journal of Medicinal Chemistry, 107, 219–232. https://doi.org/https://doi.org/10.1016/j.ejmech.2015.10.046
   PubMed Web of Science ®Google Scholar
• Shaikh, S., Dhavan, P., Ramana, M., & Jadhav, B. (2020). Design, synthesis and evaluation of new chromone-derived aminophosphonates as potential acetylcholinesterase inhibitor. Molecular Diversity, 1–15.
   PubMed Web of Science ®Google Scholar
• Shakhatreh, M. A. K., Al-Smadi, M. L., Khabour, O. F., Shuaibu, F. A., Hussein, E. I., & Alzoubi, K. H. (2016). Study of the antibacterial and antifungal activities of synthetic benzyl bromides, ketones, and corresponding chalcone derivatives. Drug Design, Development and Therapy, 10, 3653–3660. https://doi.org/https://doi.org/10.2147/DDDT.S116312
   PubMedGoogle Scholar
• Singh, A. K., Saxena, G., & Arshad, M. (2017). Synthesis, characterization and biological evaluation of ruthenium flavanol complexes against breast cancer. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 180, 97–104. https://doi.org/https://doi.org/10.1016/j.saa.2017.02.056
   PubMed Web of Science ®Google Scholar
• Sun, K., Bai, Y., Zhao, R., Guo, Z., Su, X., Li, P., & Yang, P. (2019). Neuroprotective effects of matrine on scopolamine-induced amnesia via inhibition of AChE/BuChE and oxidative stress. Metabolic Brain Disease, 34(1), 173–181. https://doi.org/https://doi.org/10.1007/s11011-018-0335-y
   PubMed Web of Science ®Google Scholar
• Tapas, A. R., Sakarkar, D., & Kakde, R. (2008). Flavonoids as nutraceuticals: A review. Tropical Journal of Pharmaceutical Research, 7(3), 1089–1099. https://doi.org/https://doi.org/10.4314/tjpr.v7i3.14693
   Web of Science ®Google Scholar
• Uriarte-Pueyo, I., & I Calvo, M. (2011). Flavonoids as acetylcholinesterase inhibitors. Current Medicinal Chemistry, 18(34), 5289–5302. https://doi.org/https://doi.org/10.2174/092986711798184325
   PubMed Web of Science ®Google Scholar
• Wang, T. Y., Li, Q., & Bi, K. S. (2018). Bioactive flavonoids in medicinal plants: Structure, activity and biological fate. Asian Journal of Pharmaceutical Sciences, 13(1), 12–23. https://doi.org/https://doi.org/10.1016/j.ajps.2017.08.004
   PubMed Web of Science ®Google Scholar
• Xie, S.-S., Lan, J.-S., Wang, X., Wang, Z.-M., Jiang, N., Li, F., Wu, J.-J., Wang, J., & Kong, L.-Y. (2016). Design, synthesis and biological evaluation of novel donepezil–coumarin hybrids as multi-target agents for the treatment of Alzheimer’s disease. Bioorganic & Medicinal Chemistry, 24(7), 1528–1539. https://doi.org/https://doi.org/10.1016/j.bmc.2016.02.023
   PubMed Web of Science ®Google Scholar
• Yerdelen, K. O., Koca, M., Anil, B., Sevindik, H., Kasap, Z., Halici, Z., Turkaydin, K., & Gunesacar, G. (2015). Synthesis of donepezil-based multifunctional agents for the treatment of Alzheimer’s disease. Bioorganic & Medicinal Chemistry Letters, 25(23), 5576–5582. https://doi.org/https://doi.org/10.1016/j.bmcl.2015.10.051
   PubMed Web of Science ®Google Scholar
• You, J., Fu, H., Zhao, D., Hu, T., Nie, J., & Wang, T. (2020). Flavonol dyes with different substituents in photopolymerization. Journal of Photochemistry and Photobiology A: Chemistry, 386, 112097. https://doi.org/https://doi.org/10.1016/j.jphotochem.2019.112097
   Web of Science ®Google Scholar