Synthesis and Biological Evaluation of Flavonoids as Antiacetyl- cholinesterase Agent
DOI:
https://doi.org/10.11113/jt.v69.2588Keywords:
Flavonoids, chalcone, flavone, flavanone, acetylcholinesteraseAbstract
A series of chalcones, a flavone and one flavanone were synthesized and elucidated structurally by IR and 1H NMR spectroscopies. The synthetic compounds were then screened for acetylcholinesterase inhibitory activity using thin layer chromatography (TLC) and microplate assays. In the TLC assay, only 2′-hydroxy-4-methoxychalcone and 2′-hydroxy-4′-O-prenyl-2,6-dichlorochalcone were found to show moderate and weak activity respectively against acetylcholinesterase (AchE) at 0.1 mM concentration compared to the control galanthamine. 4′-Hydroxy-2,6-dichlorochalcone, 2′-hydroxy-4-nitrochalcone, 2′-hydroxy-4-(dimethyl)aminochalcone and 2′-hydroxy-4-methoxychalcone showed moderate AchE inhibitory activity with percentage inhibition of 54.24, 46.14 and 49.32 % respectively in the microplate assay.
References
Kutaiba, I. A., Mohamed, A. M. 2012. Chemistry, Biochemistry and Antioxidant Activity. Journal of Pharmacy Research. 5(8): 4013–4020.
Srinivasa, M. R., Kotesh, J., Narukulla, R., Duddeck., H. 2004. Synthesis and Spectroscopic Characterization of Some Chromanochalcones and Their Dihydro Derivatives. Archive of Organic Chemistry. 14: 96–102.
Reddy, C. S., Nagaraj, A. 2008. Synthesis and Biological Study of Novel Bis-chalcones, Bis-thiazines and Bis-pyrimidines. Journal of the Iranian Chemical Society. Soc. 5: 262–267.
Hamdi, N., Fischmeister, C., Puerta, M. C., Valerga, P. 2010. A Rapid Access to New Coumarinylchalcone and Substituted Chromeno [4,3-c]pyrazol-4(1H)-ones and Their Antibacterial and DPPH Radical Scavenging Activities. Medicinal Chemistry Research. 19: 1–16.
Kamal, A., Prabhakar, S., Ramaiah, M. J., Reddy, P. V., Reddy, C. R., Mallareddy, A., Shankaraiah, Lakshmi, Narayan, Reddy, T. L. N., Pushpavalli, S. N. C. V. L., Pal-Bhadra, M. 2011. Synthesis and Anticancer Activity of Chalcone-pyrrolobenzodiazepine Conjugates Linked Via 1,2,3-Triazole Ring Side-armed with Alkane Spacers. European Journal of Medicinal Chemistry. 46: 3820–3831.
Niti, G. G., Rajput, P. R., Banewar, V. W., Raut, A. R. 2012. Synthesis and Antimicrobial Activity of Some Chalcones and Flavones Having 2-Hydroxy Acetophenone Moiety. International Journal of Pharma and Bio Science. 3(3): 389–395.
Prashar, H., Chawla, A., Sharma, A. K., Kharb, R. 2012. Chalcone as a Versatile Moiety for Diverse Pharmacological Activities. International Journal of Pharmaceutical Sciences and Research. Sci. Res. 3(7): 1913–1927.
Bano, S., Javed, K., Ahmad, S., Rathish, I. G., Singh, S., Chaitanya, M., Arunasree, K. M., Alam, M. S. 2013. Synthesis of Some Novel Chalcones, Flavanones and Flavones and Evaluation of Their Anti-inflammatory Activity. European Journal of Medicinal Chemistry. 65: 51–59.
Dimmock, J. R., Kandepu, N. M., Hetherington, M., Quail, J. W., Pugazhenthi, U., Sudom, A. M., Chamankhah, M., Rose, P., Pass, E., Allen, T. M., Halleran, S., Szydlowski, J., Mutus, B., Tannous, M., Manavathur, E. K., Myers, T. G., De Clercq, E., Balzarini, J. 1998. Cytotoxic Activities of Mannich Bases of Chalcones and Related Compounds. Journal of Medicinal Chemistry. 41: 1014–1026.
Bakthir, H., Ali, N. A. A., Arnold, N., Teichert, A., Wessjohann, L. 2011. Anticholinesterase Activity of Endemic Plant Extracts from Soqotra. African Journal of Traditional Complement and Alternative Medicine. 8(3): 296–299.
Sugamoto, K., Matsusita, Y., Matsui, K., Kurogi, C., Matsui, T. 2011. Synthesis and Antibacterial Activity of Chalcones Bearing Prenyl or Geranyl Groups from Angelica keiskei. Tetrahedron Letters. 67: 5346–5359.
Huang, W., Chien, P., Yang, C., Lee, A., 2003. Novel synthesis of flavonoids of Scutellaria baicelensis. Chemical and Pharmaceutical Bulletin. 51: 339–340.
Sharma, A., Anand, N., Sharma, R., Chaturvedi, U., Khanna, A. K., Bhatia, G., Tripathi, R. P. 2012. Synthesis of 5-aryl-6-cinnamoyl-7-methyl-Flavanones as Novel Antioxidants and Antihyperlipidemics. Journal of Enzyme Inhibition and Medicinal Chemistry. 27(2): 211–22.
Kamboj, R. C., Arora, R., Sharma, G., Kumar, D., Sharma, C., Joshi, R. Aneja, K. R. 2010. Eco-friendly Synthesis and Antimicrobial Activity of Chalcones. Der PharmaChemica. 2(3): 157–170.
Singh, H. P., Pandeya, S. N., Chauhan, C. S., Chandra, Shekhar, Sharma, C. S. 2011. Synthesis and Pharmacological Screening of Some Novel Chalconyl Derivatives of Substituted Phenyl Semicarbazide. Medicinal Chemistry Research. 20: 74–80.
Ahmed, N., Ali, H., van Lier, J. E. 2005. Silica Gel Supported InBr3 and InCl3: New Catalysts for the Facile and Rapid Oxidation of 2-Hydroxychalcones and Flavanones to Their Corresponding Flavones Under Solvent Free Conditions. Tetrahedron Letters. 46: 253–256.
Ohkatsu, Y., Satoh, T. 2008. Antioxidant and Photo-antioxidant Activities of Chalcone Derivatives. Journal of the Japan Petroleum Institute. 51(5): 298–308.
Bombardelli, E., Valenti, P. 2002. Preparation of Chalcones having Antiproliferative Activity. US 6423740 B1 20020723. 1–10.
Kumar, D., Patel, G., Kumar, A., Roy, Ram, K. 2009. Ionic liquid catalyzed expeditious synthesis of 2-aryl-2,3-dihydroquinolin-4(1H)-ones and 2-aryl-2,3-dihydro-4H-chromen-4-ones Under Microwave Irradiation. Journal of Heterocyclic Chemistry. 46(4): 791–795.
Ellman, G. L., Courtney, D., Andles, V., Featherstone, R. M. 1961. Biochem. Pharm. 7: 88–95.
Rhee, I. K., van Rijn, R. M., Verpoorte, R. 2003. Qualitative Determination of False-positive Effects in the Acetylcholinesterase Assay Using Thin Layer Chromatography. Phytochemical Analysis. 14: 127–131.
Yoon, Y. K., Mohamed Ashraf Ali, A. A., Wei, A. C., Tan Soo Choon,T. S., Khaw, K. Y., Murugaiyah, V., Osman, H., Masand, V. H. 2013. Synthesis, Characterization, and Molecular Docking Analysis of Novel Benzimidazole Derivatives as Cholinesterase inhibitors. Bioorganic Chemistry. 49: 33–39.
Downloads
Published
Issue
Section
License
Copyright of articles that appear in Jurnal Teknologi belongs exclusively to Penerbit Universiti Teknologi Malaysia (Penerbit UTM Press). This copyright covers the rights to reproduce the article, including reprints, electronic reproductions, or any other reproductions of similar nature.