Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities
Asian Journal of Chemical Sciences,
Page 1-16
DOI:
10.9734/ajocs/2019/v6i318996
Abstract
Chalcones are useful intermediates in the synthesis of heterocyclic compound and the unique reagents in organic synthesis. The usual approach to obtain chalcones is through Claisen-Schmidt condensation. Several novel heterocyclic chalcone analogs have emerged. Chalcones are multifunctional molecules that possess promising pharmacological activities. Chalcones are known for anti-cancer, antioxidant, anti-inflammatory, anti-microbial, anti-tubercular, antileishmanial, antimalarial, anthelmintic, osteogenic activities. This review article focuses on recent applications of Claisen-Schmidt condensation reaction employed in the synthesis of chalcone, its transformation to heterocyclic compounds and pharmacological activities.
Keywords:
- Chalcone
- heterocycles
- synthesis
- pharmacological activities.
How to Cite
Ovonramwen, O., Owolabi, B., & Oviawe, A. (2019). Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities. Asian Journal of Chemical Sciences, 6(3), 1-16. https://doi.org/10.9734/ajocs/2019/v6i318996
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Guchhait SK, Hura N, Shah AP. Synthesis of polysubstituted 2-aminoimidazoles via alkene-diamination of guanidine with conjugated α-bromoalkenones. J Org Chem. 2017;82:2745-2752.
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Williams IS, Joshicd P, Gatchie L, Sharma M, Sattie NK, Vishwakarma RA, Chaudhuri B, Bharate SB. Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance. Bioorg. Med. Chem. Lett. 2017;27(16):3683-3687.
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Gupta S, Maurya P, Upadhyay A, Kushwaha P, Krishna S, Siddiqi MI, Sashidhara KV, Banerjee D. Synthesis and bio-evaluation of indole-chalcone based benzopyrans as promising anti ligase and antiproliferative agents. Eur J Med Chem. 2018;143:1981-1996.
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Lahsasni SA, Al Korbi FH, Aljaber NAA. Synthesis, characterization, and evaluation of antioxidant activities of some novel chalcones analogs. Chem Cent J. 2014;8(32):1-10.
DOI: 10.1186/1752-153X-8-32
Díaz-Carrillo JT, Díaz-Camacho SP, Delgado-Vargas F, Rivero IA, López-Angulo G, Sarmiento-Sánchez JI, Montes-Avila J. Synthesis of leading chalcones with high antiparasitic, against Hymenolepis nana, and antioxidant activities. Braz J Pharm Sci. 2018;54(3): e17343.
DOI: 10.1590/s2175-97902018000317343
Stepanic´ V, Matijašic´ M, Horvat T, Verbanac D, -Chlupácˇová MK, Saso L, Žarkovic´N. Antioxidant activities of alkyl substituted pyrazine derivatives of chalcones—In vitro and In silico study. Antioxidants. 2019;8(90):1-11.
DOI: 10.3390/antiox8040090
Wang J, Huang L, Cheng C, Li G, Xie J, Shen M, Chen Q, Li W, He W, Qiu P, Wu J. Design, synthesis and biological evaluation of chalcone analogs with novel dual antioxidant mechanisms as potential anti-ischemic stroke agents. Acta Pharm Sin B. 2019;9(2):335–350.
DOI: 10.1016/j.apsb.2019.01.003
Rücker H, Al-Rifai N, Rascle A, Gottfried E, Brodziak-Jarosz L, Gerhäuser C, Dickd TP, Amslinger S. Enhancing the anti-inflammatory activity of chalcones by tuning the Michael acceptor site. Org Biomol. Chem. 2015;13(1):3040-3047.
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Debarshi KM, Ruchi SS. Anti-inflammatory potential of a novel imidazole containing murrayanine based chalcone. Mod Appl Pharm Pharmacol. 2018;2(2). MAPP.000533.
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Shih TL, Liu MH, Li CW, Kuo CF. Halo-substituted chalcones and azachalcones inhibited lipopolysaccharited-stimulated pro-inflammatory responses through the TLR4-mediated pathway. Molecules. 2018;23(3):597.
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Thasneem CK, Biju CR, Babu G. Synthesis and antimicrobial study of chalcone linked 1,3,4-oxadiazole derivatives. World J Pharm Pharm. Sc. 2015;4(1):643-655.
Burmaoglu S, Algul O, Gobek A, Anil DA, Ulger M, Erturk BG, Kaplan E, Dogen A, Aslan G. Design of potent fluoro-substituted chalcones as antimicrobial agents. J Enzyme Inhib Med Chem. 2017;32(1):490-495.
DOI: 10.1080/14756366.2016.1265517
Bathelemy N, Charles FN, Pantaleon A, Azeh NN, Estella T, Hortense GK, Aghem FK, Ronel TA, Olivier AK, Ngadjui BT. Synthesis and evaluation of antimicrobial properties of some chalcones. Br J Pharm Res. 2016;14(2):1-11.
DOI: 10.9734/BJPR/2016/28243
Osmaniye D, Kaya Çavuşoğlu B, Sağlık BN, Levent S, Acar Çevik U, Atlı Ö, Özkay Y, Kaplancıklı ZA. Synthesis and anticandidal activity of new imidazole-chalcones. Molecules. 2018;23(4)pii:E831.
DOI: 10.3390/molecules23040831
Alam S, Panda R, Kachroo M. Anti-tubercular, antioxidant, and in the vitro anti-inflammatory activity of some newly synthesized chalcones. Ind J Chem. 2014;53B:440-443.
Solankee A, Tailor R. An efficient synthesis of some new chalcone, acetyl pyrazoline and aminopyrimidine bearing 1,3,5-triazine nucleus as a potential antimicrobial and antitubercular agent. Chem Int. 2016;2(4): 189-200.
Gupta S, Shivahare R, Korthikunta V, Singh R, Gupta S, Tadigoppula N. Synthesis and biological evaluation of chalcones as potential antileishmanial agents. Eur J Med Chem. 2014;23(81): 359-66.
Syahri J, Yuanita E, Nurohmah BA, Armunanto R, Purwono B. Chalcone analog as potent anti-malarial compounds against Plasmodium falciparum: Synthesis, biological evaluation and docking simulation study. Asian Pac. J. Trop. Biomed. 2017;7(8):675–679.
DOI: 10.1016/j.apjtb.2017.07.004
Yadav N, Dixit SK, Bhattacharya A, Mishra LC, Sharma M, Awasthi SK, Bhasin VK. Antimalarial activity of newly synthesised chalcone derivatives in vitro. Chem Biol Drug Des. 2016;80(2):340–34.
DOI: 10.1111/j.1747-0285.2012.01383.x
Epub 2012 Apr 13.
Tomar N, Singh SV, Cl J, Verma G, Pal A, Sing V. Synthesis and antiplasmodial activity of some novel chalcone derivatives. Asian J. Pharm. Clin. Res. 2015;8(2):47-50.
Maurya SW, Dev K, Prakash R, John AA, Siddiqui IR, Singh D, Maurya R. Design and synthesis of indolyl chalcone analogues and evaluation of their osteogenic activity. J. Pharmacol. Pharm. Res. 2018;1(2):006.
Ali MF, Khlafulla AM, Mohamed R. Synthesis of benzimidazole derived chalcones and their heterocyclic derivatives. I.J.E.A.S. 2016;3(6):13-16.
Rajkumar T, Siva SRL, Shah F, Anwar HS. Insilico design, synthesis, characterization and biological evaluation of some hydroxynapthelene-2-yl derivatives. Int J Curr Res. 2017;9(5):51384-51391.
Dhananjayulu M, Prasad SS, Swarupa CH, Seenu Naik M, Sreedhar NY. Synthesis characterization and electrochemical behavior of 2-hydroxy chalcones using silica gel supported piperidine. I. J. I. R. S. E. T. 2014;3(5):12496-12501.
Perrin CL, Chang KL. The complete mechanism of an Aldol condensation. J Org Chem.; 2016.
DOI: 10.1021/acs.joc.6b00959
Zhu Y, Li C, Zhang J, She M, Sun W, Wan K, Wang Y, Yin B, Liu P, Li J. A facile FeCl3/I2-catalyzed aerobic oxidative coupling reaction: Synthesis of tetrasubstituted imidazoles from amidines and chalcone. Org Lett. 2015;17:3872-3875.
DOI: 10.1021/acs.orglett.5b01854
DOI: 10.1021/jo501844x
Ding Y, Zhang T, Chen Q-Y, Zhu C. Visible-light photocatalytic aerobic annulation for the green synthesis of pyrazoles. Org Lett. 2016;18:4206-4209.
DOI: 10.1021/acs.orglett.6b01867
Imbri D, Netz N, Kucukdisli M, Kammer LM, Jung P, Kretzschmann A, Opatz T. One-Pot synthesis of Pyrrole-2-carboxylates and -carboxamides via an electrocyclization/oxidation sequence. J Org Chem. 2014;79:11750-11758.
DOI: 10.1021/jo5021823
Wang Y, Jiang C-M, Li H-L, He F-S, Luo X, Deng W-P. Regioselective iodine-catalyzed construction of polysubstituted pyrroles from allenes and enamines. J Org Chem. 2016;81:8653-8658.
DOI: 10.1021/acs.joc.6b01737
Chen D, Chen Y, Ma Z, Zou L, Li J, Liu Y. One-pot synthesis of indole-3-acetic acid derivatives through the cascade Tsuji-Trost reaction and heck coupling. J Org Chem. 2018;83:6805-6814.
DOI: 10.1021/acs.joc.8b01056
Osman ABM, Nour AH, Ali DMH, Osman HA, Saeed AEM. Design and synthesis of 2-pyrazoline derivatives. Pharm Lettre. 2016;8(1):8-11.
Dou G, Xu P, Li Q, Xi Y, Huang Z, Shi D. Clean and efficient synthesis of isoxazole derivatives in aqueous media. Molecules. 2013;18:13645-13653.
DOI: 10.3390/molecules181113645
de Souza AAN, Xavier VF, Coelho GS, Junior PAS, Romanha AJ, Murta SMF, Carneiroc CM, Taylor JG. Synthesis of 3,5-diarylisoxazole derivatives and evaluation of in vitro trypanocidal activity. J Braz Chem Soc. 2018;29(2):269-277.
DOI: 10.21577/0103-5053.20170137
Kalirajan R, Rafick MHM, Sankar S, Gowramma B. Green synthesis of some novel chalcone and isoxazole substituted 9-anilino acridine derivatives and evaluation of their biological and larvicidal activities. Indian J Chem B. 2018;57B:583-590.
Aswin K, Mansoor SS, Logaiya K, Sudhan SPN. Triphenylphosphine: An efficient catalyst for the synthesis of 4,6-diphenyl-3,4-dihydropyrimidine-2(1H)-thione under thermal conditions. J. K. S. U. S. 2014;26(12):141–148.
Sahoo BM, Rajeswari M, Jnyanaranjan P, Binayani S. Green expedient synthesis of pyrimidine derivatives via chalcones and evaluation of their anthelmintic activity. Indian J Pharm Educ. 2017;51(4S):S700-S6.
Huang H, Cai J, Tang L, Wang Z, Li F, Deng G-J. Metal-free assembly of polysubstituted pyridines from oximes and acroleins. J Org Chem. 2016;81:1499-1505.
DOI: 10.1021/acs.joc.5b02624
Song Z, Huang X, Yi W, Zhang W. One-pot reactions for modular synthesis of polysubstituted and fused pyridines. Org Lett. 2016;18:5640-5643.
DOI: 10.1021/acs.orglett.6b02883
Chen G, Wang Z, Zhang X, Fan X. Synthesis of functionalized pyridines via Cu(II)-catalyzed one-pot cascade reactions of inactivated saturated ketones with electron-deficient enamines. J Org Chem. 2017;82:11230-11237.
DOI: 10.1021/acs.joc.7b01901
Cheng G, Xue L, Weng Y, Cui X. Transition-metal-free cascade approach toward 2-Alkoxy/2-Sulfenylpyridines and Dihydrofuro[2,3-b]pyridines by trapping in situ generated 1,4-Oxazepine. J Org Chem. 2017;82:9515-9524.
DOI: 10.1021/acs.joc.7b01541
Abd El-Sattar NEA, Badawy EHK, Abdel-Mottale MSA. Synthesis of some pyrimidine, pyrazole, and pyridine derivatives and their reactivity descriptors. J Chem. 2018;11. Article ID: 8795061.
DOI: 10.1155/2018/8795061
Yang L, Wu Y, Yang Y, Wen C, Wan JP. Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide. Beilstein J Org Chem. 2018;14:2348-2353.
DOI: 10.3762/bjoc.14.210
Wan J-P, Cao S, Liu Y. Base-promoted synthesis of N-substituted 1,2,3-Triazoles via enaminone-azide cycloaddition involving regitz diazo transfer. Org Lett. 2016;18:6034-6037.
DOI: 10.1021/acs.orglett.6b03016
Rajaguru K, Suresh R, Mariappan A, Muthusubramanian S, Bhuvanesh N. Erbium triflate promoted the multicomponent synthesis of highly substituted imidazoles. Org Lett. 2014;16(3):744-747.
DOI: 10.1021/ol403456b
Guchhait SK, Hura N, Shah AP. Synthesis of polysubstituted 2-aminoimidazoles via alkene-diamination of guanidine with conjugated α-bromoalkenones. J Org Chem. 2017;82:2745-2752.
DOI: 10.1021/acs.joc.6b03021
Jayaseelan D, Ganapathi M, Guhanathan S. Microwave-assisted synthesis of 4,6-diphenyl substituted thiazine derivatives and its characterization. Organic Chemistry: An Indian Journal (O.C.A.I.J.). 2015;11(8):305-311.
El-Gaml KM. Application of chalcone in synthesis of new heterocycles containing 1,5-benzodiazepine derivatives. American Journal of Organic Chemistry. 2014;4(1): 14-19.
DOI: 10.5923/j.ajoc.20140401.03
Özdemir A, Altıntop MD, Sever B, Gençer HK, Kapkaç HA, Atlı Ö, Baysal MA. New series of pyrrole-based chalcones: Synthesis and evaluation of antimicrobial activity, cytotoxicity, and genotoxicity. Molecules. 2017;22:2112.
DOI: 10.3390/molecules22122112
Williams IS, Joshicd P, Gatchie L, Sharma M, Sattie NK, Vishwakarma RA, Chaudhuri B, Bharate SB. Synthesis and biological evaluation of pyrrole-based chalcones as CYP1 enzyme inhibitors, for possible prevention of cancer and overcoming cisplatin resistance. Bioorg. Med. Chem. Lett. 2017;27(16):3683-3687.
DOI: 10.1016/j.bmcl.2017.07.010
Gupta S, Maurya P, Upadhyay A, Kushwaha P, Krishna S, Siddiqi MI, Sashidhara KV, Banerjee D. Synthesis and bio-evaluation of indole-chalcone based benzopyrans as promising anti ligase and antiproliferative agents. Eur J Med Chem. 2018;143:1981-1996.
DOI: 10.1016/j.ejmech.2017.11.015
Lahsasni SA, Al Korbi FH, Aljaber NAA. Synthesis, characterization, and evaluation of antioxidant activities of some novel chalcones analogs. Chem Cent J. 2014;8(32):1-10.
DOI: 10.1186/1752-153X-8-32
Díaz-Carrillo JT, Díaz-Camacho SP, Delgado-Vargas F, Rivero IA, López-Angulo G, Sarmiento-Sánchez JI, Montes-Avila J. Synthesis of leading chalcones with high antiparasitic, against Hymenolepis nana, and antioxidant activities. Braz J Pharm Sci. 2018;54(3): e17343.
DOI: 10.1590/s2175-97902018000317343
Stepanic´ V, Matijašic´ M, Horvat T, Verbanac D, -Chlupácˇová MK, Saso L, Žarkovic´N. Antioxidant activities of alkyl substituted pyrazine derivatives of chalcones—In vitro and In silico study. Antioxidants. 2019;8(90):1-11.
DOI: 10.3390/antiox8040090
Wang J, Huang L, Cheng C, Li G, Xie J, Shen M, Chen Q, Li W, He W, Qiu P, Wu J. Design, synthesis and biological evaluation of chalcone analogs with novel dual antioxidant mechanisms as potential anti-ischemic stroke agents. Acta Pharm Sin B. 2019;9(2):335–350.
DOI: 10.1016/j.apsb.2019.01.003
Rücker H, Al-Rifai N, Rascle A, Gottfried E, Brodziak-Jarosz L, Gerhäuser C, Dickd TP, Amslinger S. Enhancing the anti-inflammatory activity of chalcones by tuning the Michael acceptor site. Org Biomol. Chem. 2015;13(1):3040-3047.
DOI: 10.1039/C4OB02301C
Debarshi KM, Ruchi SS. Anti-inflammatory potential of a novel imidazole containing murrayanine based chalcone. Mod Appl Pharm Pharmacol. 2018;2(2). MAPP.000533.
DOI: 10.31031/MAPP.2018.02.000533
Shih TL, Liu MH, Li CW, Kuo CF. Halo-substituted chalcones and azachalcones inhibited lipopolysaccharited-stimulated pro-inflammatory responses through the TLR4-mediated pathway. Molecules. 2018;23(3):597.
DOI: 10.3390/molecules23030597
Thasneem CK, Biju CR, Babu G. Synthesis and antimicrobial study of chalcone linked 1,3,4-oxadiazole derivatives. World J Pharm Pharm. Sc. 2015;4(1):643-655.
Burmaoglu S, Algul O, Gobek A, Anil DA, Ulger M, Erturk BG, Kaplan E, Dogen A, Aslan G. Design of potent fluoro-substituted chalcones as antimicrobial agents. J Enzyme Inhib Med Chem. 2017;32(1):490-495.
DOI: 10.1080/14756366.2016.1265517
Bathelemy N, Charles FN, Pantaleon A, Azeh NN, Estella T, Hortense GK, Aghem FK, Ronel TA, Olivier AK, Ngadjui BT. Synthesis and evaluation of antimicrobial properties of some chalcones. Br J Pharm Res. 2016;14(2):1-11.
DOI: 10.9734/BJPR/2016/28243
Osmaniye D, Kaya Çavuşoğlu B, Sağlık BN, Levent S, Acar Çevik U, Atlı Ö, Özkay Y, Kaplancıklı ZA. Synthesis and anticandidal activity of new imidazole-chalcones. Molecules. 2018;23(4)pii:E831.
DOI: 10.3390/molecules23040831
Alam S, Panda R, Kachroo M. Anti-tubercular, antioxidant, and in the vitro anti-inflammatory activity of some newly synthesized chalcones. Ind J Chem. 2014;53B:440-443.
Solankee A, Tailor R. An efficient synthesis of some new chalcone, acetyl pyrazoline and aminopyrimidine bearing 1,3,5-triazine nucleus as a potential antimicrobial and antitubercular agent. Chem Int. 2016;2(4): 189-200.
Gupta S, Shivahare R, Korthikunta V, Singh R, Gupta S, Tadigoppula N. Synthesis and biological evaluation of chalcones as potential antileishmanial agents. Eur J Med Chem. 2014;23(81): 359-66.
Syahri J, Yuanita E, Nurohmah BA, Armunanto R, Purwono B. Chalcone analog as potent anti-malarial compounds against Plasmodium falciparum: Synthesis, biological evaluation and docking simulation study. Asian Pac. J. Trop. Biomed. 2017;7(8):675–679.
DOI: 10.1016/j.apjtb.2017.07.004
Yadav N, Dixit SK, Bhattacharya A, Mishra LC, Sharma M, Awasthi SK, Bhasin VK. Antimalarial activity of newly synthesised chalcone derivatives in vitro. Chem Biol Drug Des. 2016;80(2):340–34.
DOI: 10.1111/j.1747-0285.2012.01383.x
Epub 2012 Apr 13.
Tomar N, Singh SV, Cl J, Verma G, Pal A, Sing V. Synthesis and antiplasmodial activity of some novel chalcone derivatives. Asian J. Pharm. Clin. Res. 2015;8(2):47-50.
Maurya SW, Dev K, Prakash R, John AA, Siddiqui IR, Singh D, Maurya R. Design and synthesis of indolyl chalcone analogues and evaluation of their osteogenic activity. J. Pharmacol. Pharm. Res. 2018;1(2):006.
Ali MF, Khlafulla AM, Mohamed R. Synthesis of benzimidazole derived chalcones and their heterocyclic derivatives. I.J.E.A.S. 2016;3(6):13-16.
Rajkumar T, Siva SRL, Shah F, Anwar HS. Insilico design, synthesis, characterization and biological evaluation of some hydroxynapthelene-2-yl derivatives. Int J Curr Res. 2017;9(5):51384-51391.
Dhananjayulu M, Prasad SS, Swarupa CH, Seenu Naik M, Sreedhar NY. Synthesis characterization and electrochemical behavior of 2-hydroxy chalcones using silica gel supported piperidine. I. J. I. R. S. E. T. 2014;3(5):12496-12501.
Perrin CL, Chang KL. The complete mechanism of an Aldol condensation. J Org Chem.; 2016.
DOI: 10.1021/acs.joc.6b00959
Zhu Y, Li C, Zhang J, She M, Sun W, Wan K, Wang Y, Yin B, Liu P, Li J. A facile FeCl3/I2-catalyzed aerobic oxidative coupling reaction: Synthesis of tetrasubstituted imidazoles from amidines and chalcone. Org Lett. 2015;17:3872-3875.
DOI: 10.1021/acs.orglett.5b01854
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