ABSTRACT:

Despite their discovery in the early nineteenth century, chalcone compounds have evolved and played a significant role in medical and industrial applications. The most important feature of these compounds is that they contain two active groups (C=O and C=C), which give high biological effectiveness to pharmaceutical compounds. In both their synthetic and natural forms, chalcones have demonstrated a variety of biological properties, including antifungal, antibacterial, antioxidant, antimitotic, antimalarial, and antiviral properties. This review included preparation methods, cofactors used, chemical reactions, and biological applications for the last years.

KEYWORDS :

Chalcones: Preparation methods, Reactions, Biological activities

REFERENCES : 

1) Steffi I. Gonsalves, Shaikh A. R.;(2012). 2D QSAR Analysis of 3’, 4’, 5’-Trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation, Journal of Computational Methods in Molecular Design, 2(1), 24-38.
2) Thanh-Dao T., Haeil P., Gerhard F. Ecker, Khac-Minh T., (2008) 2′-Hydroxychalcone Analogues: Synthesis and Structure-PGE2 Inhibitory Activity Relationship, International electronic conference on synthetic organic chemistry, 1-7.
3) Straub TS. (1995). Epoxidation of α, β-unsaturated ketones with sodium perborate. Tetrahedron Lett, 1995; 36(5):663–4.
4) Opletalova V, Hartl J, Palat KJr, Patel A. (2000) Conformational analysis of 2-hydroxy-2¢,5¢- diazachalcones.J Pharm Biomed Anal 23: 55-59.
5) Benouda H, Bouchal B, Challioui A, Oulmidi A, Harit T, Malek F, Riahi A, Bellaoui M, Bouammali B. (2019). Synthesis of a series of chalcones and related flavones and evaluation of their antibacterial and antifungal activities. Lett Drug Des Discov, 16(1):93–100.
6) Choudhary AN, Kumar A, Juygal V. (2012). Design, Synthesis and evaluation of chalcone derivatives as anti-inflammatory, antioxidant and antiulcer agents. Lett Drug Des Discov, 9(5):479–88.
7) Bandgar BP, Gawande SS, Bodade RG, Totre JV, Khobragade CN., (2010) Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. Bioorg Med Chem; 18(3):1364–70.
8) Dhar R, Kimseng R, Chokchaisiri R, Hiransai P, Utaipan T, Suksamrarn A, Chunglok W. (2018). 2′, 4-Dihydroxy-3′, 4′, 6′-trimethoxychalcone from chromolaena odorata possesses anti-inflammatory effects via inhibition of NF-κB and p38 MAPK in lipopolysaccharide-activated RAW 264.7 macrophages. Immunopharmacol Immunotoxicol, 40(1):43–51.
9) Fu ZY, Jin QH, Qu YL, Guan LP. (2019). Chalcone derivatives bearing chromen or benzo [f] chromen moieties: design, synthesis and evaluations of anti-inflammatory, analgesic, selective COX-2 inhibitory activities. Bioorg Med Chem Lett, 29:1909–12
10) Pingaew R, Saekee A, Mandi P, Nantasenamat C, Prachayasittikul S, Ruchirawat S, Prachayasittikul V. (2014). Synthesis, biological evaluation and molecular docking of novel chalcone–coumarin hybrids as anticancer and antimalarial agents. Euro J Med Chem, 85:65–76.
11) Hofmann E, Webster J, Do T, Kline R, Snider L, Hauser Q, Higginbottom G, Campbell A, Ma L, Paula S. (2016). Hydroxylated chalcones with dual properties: xanthine oxidase inhibitors and radical scavengers. Bioorg Med Chem, 24(4):578–87.
12) Padaratz P, Fracasso M, De Campos-Buzzi F, Corrêa R, Niero R, Monache FD, Cechinel-Filho V. (2009) Antinociceptive activity of a new benzofuranone derived from a chalcone. Basic Clin Pharmacol Toxicol, 105(4):257–61.
13) Gan FF, Zhang R, Ng HL, Karuppasamy M, Seah W, Yeap WH, Ong SM, Hadadi E, Wong SC, Chui WK, Chew EH. (2018) Novel dual-targeting anti-proliferative dihydrotriazine chalcone derivatives display suppression of cancer cell invasion and inflammation by inhibiting the NF-κB signaling pathway. Food Chem Toxicol, 116:238–48.
14) Insuasty B, Ramírez J, Becerra D, Echeverry C, Quiroga J, Abonia R, Robledo SM, Vélez ID, Upegui Y, Munoz JA, Ospina V. (2015) An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo [3, 4-b] [1, 4] diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents. Euro J Med Chem, 93:401–13.
15) Wan Z, Hu D, Li P, Xie D, Gan X. (2015). Synthesis, antiviral bioactivity of novel 4-thioquinazoline derivatives containing chalcone moiety. Molecules, 20(7):11861–74.
16) Balu P, Jas JS, Govindaraj M. (2019). Design and evaluation of chalconeimine derivatives as α-amylase inhibitors. Bioinformation, 15(7):523–9.
17) Reddy AK, Kathale NE. (2018) Synthesis, Characterization and anti-inflammatory activity of chalcone derivatives linked with Apocynin and 5-nitrofuran moiety. Asian J Chem; 30(2):312–6.
18) Hassan, A.S., Moustafa, G.O., Morsy, N.M., Abdou, A.M. and Hafez, T.S., (2020). Design, Synthesis and antibacterial activity of N-aryl-3-(arylamino)-5-(((5-substituted furan-2-yl) methylene) amino)-1H-pyrazole-4-carboxamide as Nitrofurantoin® analogues. Egypt. J. Chem., 63 (11): 4469-4481.
19) Bianco A, Cavarischia C, Farina A, Guiso M, Marra C. (2003). A new synthesis of flavonoids via Heck reaction. Tetrahedron Lett, ; 44(51):9107–9.
20) Braun RU, Ansorge M, Mueller TJ. (2006). Coupling–isomerization synthesis of chalcones. Chemistry, ; 12(35):9081–94.
21) Ötvös, S., Hsieh, C.T., Wu, Y.C., Li, J.H., Chang, F.R. and Fülöp, F., (2016), Continuous-Flow Synthesis of Deuterium-Labeled Antidiabetic Chalcones: Studies towards the Selective Deuteration of the Alkynone Core. Molecules, 21 (3): 318-329.
22) Rueping, M., Bootwicha, T., Baars, H. and Sugiono, E., (2011), Continuous-flow hydration-condensation reaction: Synthesis of α, β-unsaturated ketones from alkynes and aldehydes by using a heterogeneous solid acid catalyst. Beilstein J. Org. Chem., 7: 1680-1687 DOI: 10.3762/bjoc.7.198
23) Kamakshi, R. and Reddy, B.S.R., (2008), Synthesis of chalcone-based fluorescent polymers: Diels-Alder reaction of chalcones and their polymerization through ROMP. J. Polym. Sci., 46 (4): 1521-1531.
24) Hery S., Kautsar U., Nia N. Dinia Rahmah, Alfinda N. Kristanti, (2017), Ni N. Tri Puspaningsih;4-({4-[(2E)-3-(2,5-Dimethoxyphenyl) prop-2-enoyl] phenyl} amino)-4-oxobutanoic Acid, Molbank ,2,1-4.
25) Nimisha S., Pandey S. K., Rama P. Tripathi; (2010), ”Regioselective [3+2] cycloaddition of chalcones with a sugar azide: easy access to 1-(5-deoxy-d-xylofuranos-5-yl)-4,5-disubstituted-1H-1,2,3-triazoles’‘, Carbohydrate Research,345(12), 1641-1648.
26) Suwito, H., Jumina, Mustofa, Kristanti, A.N. and Puspaningsih, N.N.T., (2014). Chalcones: Synthesis, structure diversity and pharmacological aspects. J. Chem. Pharm. Res., 6 (5): 1076-1088.
27) Joshi, D., Kshirsagair, M.D. and Singhal, S.,(2012). Synthesis and Biological Evaluation of Some Novel Isoxazoles and Benzodiazepines. J. Chem. Pharm., 4 (6): 3234-3238.
28) Ebraheem, H. A., (2013). Synthesis of some Pyrimidine-2-one and Pyrimidine-2-thione Compounds. Raf. J. Sci., 24 (1): 120-127.
29) Thy, C. K., Lee, Y. K., Abdullah, I., Abd Rahman, N., & Chee, C. F. (2024). Asymmetric Diels–Alder reaction of chalcone and isoprene mediated by titanium-based complexes. Synthetic Communications, 54(8), 636-644.
30) ‏Aksöz, B. E., & Ertan, R. (2011). Chemical and structural properties of chalcones I. Fabad J Pharm Sci, 36, 223-242.‏
31) Dos Santos, A. T. L., de Araújo-Neto, J. B., da Silva, M. M. C., da Silva, M. E. P., Carneiro, J. N. P., Fonseca, V. J. A., … & Morais-Braga, M. F. B. (2023). Synthesis of chalcones and their antimicrobial and drug potentiating activities. Microbial Pathogenesis, 180, 106129.‏
32) Tandel, S. N., Kasundra, D. V., & Patel, P. N. (2023). Design and synthesis of chalcone mediated novel pyrazoline scaffolds: Discovery of benzothiophene comprising antimicrobial inhibitors. Results in Chemistry, 6, 101119.‏
33) Uddin, J., Shah, S. W. A., Zahoor, M., Ullah, R., & Alotaibi, A. (2023). Chalcones: The flavonoid derivatives synthesis, characterization, their antioxidant and in vitro/in vivo antidiabetic potentials. Heliyon, 9(11).‏
34) Siddiqui, A.A., Rahman, M.A., Shaharyar, M. and Mishra, R., (2010). Synthesis And Anticonvulsant Activity Of Some Substituted 3,5-Diphenyl-2-Pyrazoline-1-Carboxamide Derivatives. Chem. Sci. J., 1 (1): 1-10 .
35) Bukhari SN, Butt AM, Amjad MW, Ahmad W, Shah VH, Trivedi AR. (2013).Synthesis and evaluation of chalcone analogues based pyrimidines as angiotensin converting enzyme inhibitors. Pak J Biol Sci, ; 16(21):1368–72.
36) Lucia Wiwid Wijayanti, Respati Tri Swasono, Wonkoo Lee and Jumina Jumina,(2021) Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent , Molecules , 26, 2698.