A Review on Chemistry, Synthesis and Biological Applications of Chalcone-based Schiff Bases
Abstract
Heterocyclic compounds are an important class of compounds in the field of pharmaceutical and synthetic organic chemistry. The Schiff bases contain azomethine linkages which are obtained by the condensation of aldehyde/ketone with amines. Among the various types of Schiff bases, the chalcone-based Schiff bases play a vital role in the treatment of various ailments and various applications, which can be synthesized by using different types of chalcones as the starting materials. These types of compounds were synthesized by using various techniques like conventional means of synthesis, microwave-assisted reaction, heterocyclic catalyst-mediated synthesis and also by means of trituration. The chalcone or bis-chalcone-based Schiff bases and their derivatives contain -C=N linkage which exhibits various activities including antimicrobial, anticancer, antioxidant, antidiabetic and immunosuppressant activities. Beyond these activities, these types of Schiff bases are also used in various chemical industries and fluorescent sensors, which also play a major role in the field of synthetic organic chemistry and coordination chemistry as intermediates. This review discusses the numerous synthetic strategies along with their applications in the field of medicine. Thus, this review will be helpful in developing more effective drug-like scaffolds for use in future drug design.
Keywords: Schiff bases, Chalcone-based Schiff bases, Antimicrobial, Anticancer, Antioxidant, Biological Applications
Keywords:
Schiff bases, Chalcone-based Schiff bases, Antimicrobial, Anticancer, Antioxidant, Biological ApplicationsDOI
https://doi.org/10.22270/jddt.v13i3.5969References
Raju SK, Sekar P, Kumar S, Murugesan M, Karthikeyan, Arthanari M. Biological applications of imidazothiazole scaffolds: A current review. J Adv Chem Sci. 2022; 8(1):756–69. https://doi.org/10.30799/jacs.244.22080101.
Majeed NS, Mohsen HF, Radhiyah Abdul Baqi Aldujaili RAB. Synthesis, characterization and biological activity of some new heterocyclic compounds derived from 4- aminoacetophenone. Biochem Cell Arch. 2018; 18(1):1107-16.
Raju SK, Settu A, Thiyagarajan A, Rama D, Sekar P, Kumar S. Biological applications of Schiff bases: An overview. GSC Biol Pharm Sci. 2022; 21(03):203–215. https://doi.org/10.30574/gscbps.2022.21.3.0484.
Aiwonegbe AE, Usifoh CO. Synthesis, infrared characterization and antimicrobial evaluation of Schiff bases derived from 1, 3-diphenylprop-2-en-1-one and 1-phenyl-3-(4-chlorophenyl)-prop-2-en-1-one. J Chem Soc of Niger. 2021; 46(2):0197-204. https://doi.org/10.46602/jcsn.v46i2.596
Badal MMR, Hossain MZ, Maniruzzaman M, Yousuf MA. Synthesis, identification and computational studies of novel Schiff bases N-(2,6-dibenzylidenecyclohexylidene)-N′-(2,4-dinitrophenyl)hydrazine derivatives. SN Appl Sci. 2020; 2:1914. https://doi.org/10.1007/s42452-020-03745-4.
Ahmed, AA, Mahmood, IQ, Aziz HS, Synthesis and Characterization of Few New Substituted 1,3,4-Oxadiazoles 1,2,4-Triazoles and Schiff Bases via Chalcone Compounds. Int J Drug Deliv Technol. 2022; 12(3):1087-1092. https://doi.org/10.25258/ijddt.12.3.27
Hassan SY. Synthesis, Antibacterial and Antifungal Activity of Some New Pyrazoline and Pyrazole Derivatives. Molecules. 2013; 18(3):2683-2711. https://doi.org/10.3390/molecules18032683.
Meena SK, Kumar Y. Spectral, analytical and biological studies of zinc metal complexes with substituted chalcone thiosemicarbazones. J Res Chem. 2022; 3(2):01-05.
Ibrahim TS, Almalki AJ, Moustafa AH, Allam RM, Abuo-Rahma GEA, Subbagh HIE, Mohamed MFA. Novel 1,2,4-oxadiazole-chalcone/oxime hybrids as potential antibacterial DNA gyrase inhibitors: Design, synthesis, ADMET prediction and molecular docking study. Bioorg Chem. 2021; 111:104885. https://doi.org/10.1016/j.bioorg.2021.104885.
Fandaklı S, Doğan IS & Sellitepe HE. Yaşar A. Yaylı N. Synthesis, Theoretical Calculation and α-glucosidase inhibition of new chalcone oximes. Org Commun. 2018; 11(1):23-34. https://doi.org/10.25135/acg.oc.38.18.02.067.
Muleta F, Desalegn T. Synthesis, In Silico, and Biological Applications of Novel Heteroleptic Copper (II) Complex of Natural Product-Based Semicarbazone Ligands. J Chem. 2022; 2022(1497117):1-17. https://doi.org/10.1155/2022/1497117.
Soman S, Jain P. Design, Synthesis and Study of Calamitic Liquid Crystals containing Chalcone and Schiff Base Linkages along with Terminal Alkoxy Chain. J Adv Sci Res. 2022; 13(04):59-68. https://doi.org/10.55218/jasr.202213411.
Siddiqui EJ, Azad I, Khan AR, Khan T, Thiosemicarbazone complexes as versatile medicinal chemistry agents: a review. Journal of Drug Delivery and Therapeutics, 2019; 9(3):689-703. https://doi.org/10.22270/jddt.v9i3.2888
Thakare AP, Mandlik PR. Co(II), Ni(II), Cu(II) And Cr(III) Complexes Of Heterocyclic Schiff Base Ligand: Synthesis, Spectroscopic And Thermal Study. Int J Adv Res Publ. 2017; 1(2):1-5.
Liu YT, Sheng J, Yin DW, Xin H, Yang XM, Qiao QY, Yang ZJ. Ferrocenyl chalcone-based Schiff bases and their metal complexes: Highly efficient, solvent-free synthesis, characterization, biological research. J Organometal Chem. 2018; 856:27-33. https://doi.org/10.1016/j.jorganchem.2017.12.022.
Dangwal KL, Semwal AR. Microwave-assisted synthesis and characterization of oxime derivative of substituted chalcone and its nickel(II) complex. Curr Sci. 2018; 115(3):476-481. https://doi.org/10.18520/cs/v115/i3/475-481.
Ajani OO, Jolayemi EG, Owolabi FE, Tolubolaji OO, Audu OY. Heterogeneous Acid Catalyzed Synthesis and Spectroscopic Characterization of Schiff Bases Derived from Chalcone Derivatives. Egypt J Chem. 2016; 64(1):193-200. https://doi.org/10.21608/ejchem.2020.20610.2233.
Vyas SP, Daraji KM, Darji PP, Patel PA, Goswami TK, Goswami KV. Preparation and Characterizations of (2e)-1-(4-{(E)- [(3,4,5-Trimethoxy Phenyl) Methylidene]Amino}Phenyl)- 3-Phenylprop-2-En-1-One. World J Pharm Res. 2016; 5(5):928-31. https://doi.org/10.20959/wjpr20165-6095.
Lone IH, Khan KZ, Fozdar BI, Hussain F. Synthesis antimicrobial and antioxidant studies of new oximes of steroidal chalcones. Steroids. 2013; 78(9):945-50. https://doi.org/10.1016/j.steroids.2013.05.015.
Mukhlus AA, Al-rawi MS, Tomma JH, Al-Dujaili AH. Synthesis and Characterization of New Schiffs Bases Derived from D-Erythroascorbic Acid and Pyrimidines. Ibn Al-Haitham J Pure Appl Sci. 2011; 24(2).
Patange AN, Yadav UM, Desai PA, Singare PU. Synthesis and Antimicrobial Activities of Novel Palladium (II) Complexes of Active Schiff’s Base Ligand Derived from 5-Bromo Isatin. Int Lett Chem Phys Astron. 2015; 52:22-7. https://doi.org/10.56431/p-gb7jf1.
Kalanithi M, Rajarajan M, Tharmaraj P, Sheela CD. Spectral, biological screening of metal chelates of chalcone based Schiff bases of N-(3-aminopropyl) imidazole. Spectrochim Acta A Mol Biomol Spectrosc. 2012; 87:155-62. https://doi.org/10.1016/j.saa.2011.11.031.
Rachmale PM. Synthesis and Antimicrobial Activity of Some Chalcone Derivatives and their Copper complexes. Int J Pharm Sci Res. 2012; 3(3):901-08.
Bukhari SNA. Synthesis and evaluation of new chalcones and oximes as anticancer agents. RSC Adv. 2022; 12(17):10307-20. https://doi.org/10.1039/d2ra01198k.
Luo Y, Song R, Li Y, Zhang S, Liu ZJ, Fu J, et al. Design, synthesis, and biological evaluation of chalcone oxime derivatives as potential immunosuppressive agents. Bioorg Med Chem Lett. 2012; 22(9):3039-43. https://doi.org/10.1016/j.bmcl.2012.03.080.
Radhakrishnan SK, Shimmon RG, Conn C, Baker AT. Evaluation of Novel Chalcone Oximes as Inhibitors of Tyrosinase and Melanin Formation in B16 Cells. Arch Pharm Chem Life Sci. 2016; 349(1):20-9. https://doi.org/10.1002/ardp.201500298.
Özbek N, Alp H, Çelik G, Ak T, Çağılcı OC, Yaylı N, Ocak Ü, Ocak M. A Simple Spectrofluorimetric Method for Iron Determination with a Chalcone-Based Schiff Base. J Fluoresc. 2017; 27(2):635-641. https://doi.org/10.1007/s10895-016-1992-z.
Dangwal KL, Semwal AR. Microwave Assisted Synthesis and Characterization of Oxime Derivatives of Substituted Chalcones. Int J Sci Res. 2016; 5(7):356-8.
Thakare A, Mandlik PR. Synthesis, Spectroscopic and Thermal Studies of Fe(III) and VO(IV) Complexes of Heterocyclic Schiff Base Ligand. Indian J Adv Chem Sci. 2021; 5(4):318-23. https://doi.org/10.22607/IJACS.2017.504013.
Rohini C, Arasan KT, Jagadeeshbabu V, Saritha M. Synthesis and IR Spectroscopic Characterization of some synthesized Chalcone linked Isatin Derivatives -Based Schiff Bases. Int J Curr Res. 2021; 13(10):19355-7. https://doi.org/10.24941/ijcr.42508.10.2021.
Jamel NM, Hussein DF, Tomma JH. Synthesis and Characterization New Schiff Bases,Pyrazole and Pyrazoline Compounds Derived From Acid Hydrazide Containing Isoxazoline Ring. Ibn Al-Haitham J Pure Appl Sci. 2014; 27(3):435-46.
Vyas SP. Synthesis and Characterization of New Schiff-Base Derived from (2Z)-1-(2,4- Dimethylphenyl)-3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-En-1-One. J Chem Pharm Res. 2018; 10(1):200-202.
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