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A Laconic Review on Chalcones: Synthesis, Antimicrobial and Antioxidant activities


Affiliations
1 1Department of Pharmaceutical Analysis and Quality Assurance, Laureate Institute of Pharmacy, Kathog, H.P., India, India
2 Department of Pharmacology, Maharaja Ranjit Singh Punjab Technical University, Bathinda, Punjab, India., India
3 Department of Pharmaceutical Analysis and Quality Assurance, Laureate Institute of Pharmacy, Kathog, H.P., India, India
4 Department of Pharmaceutics, Laureate Institute of Pharmacy, Kathog, H.P., India, India
5 Department of Pharmaceutical Analysis and Quality Assurance, Laureate Institute of Pharmacy, Kathog, H.P., India., India
     

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Chalcones and their derivatives have been an area of great interest for several researchers in recent years. Several number of research publications have been published and chalcones continue to show promising effect for novel drug investigations. Chalcone is an advantaged moiety with therapeutic importance as it comprises of receptive ketoethylenic moiety – CO–CH=CH– having a place with flavonoids. Chalcones (1, 3-Diphenyl-prop-2-en-1-one) consists of a three carbon α, β-unsaturated carbonyl system and two or more aromatic rings and acts as precursors for the biosynthesis of flavonoids in plants. The presence of a highly reactive α, β-unsaturated carbonyl system in chalcone and its derivatives is the justification for its pharmacological potencies. However, synthesis in laboratory of broad range of chalcones has also been reported. Chalcones show a wide range of pharmacological impacts like anthelmintic, antileishmanial, antifungal, antimalarial, antioxidant, antiviral, antibacterial, antiulcer, antimycobacterial, insecticidal, antigout, antihistaminic, antiprotozoal, insecticidal, anticancer, antidiabetic, anti-inflammatory, analgesic etc. Chalcones can be synthesized through Claisen–Schmidt's condensation, Heck's reaction, Aldol condensation reaction, Suzuki's reaction, from cinnamic acid, Sonogashira Isomerization Coupling reaction, Microwave assisted synthesis etc. The purpose of the present review is to centralize the various and widely employed methods of synthesis of chalcone and their various derivatives and their antimicrobial and antioxidant activities.

Keywords

Chalcones, Antimicrobial activity, Antioxidant activity, Claisen–Schmidt condensation, Microwave assisted synthesis.
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  • Kostanecki SV. Tambor. Synthesis, Characterization and Biological Evaluation of Some Novel Chalcone Derivatives Containing Imidazo [1, 2-a] Pyridine. Moiety J Chem. Ber. 1899; 32: 1921-9.
  • Elias DW, Beazely MA, Kandepu NM. Bioactivities of chalcones. Current Medicinal Chemistry. 1999;6(12):1125.
  • Go ML, Wu X, Liu XL. Chalcones: an update on cytotoxic and chemoprotective properties. Current Medicinal Chemistry. 2005; 12(4): 483-99.
  • Di Carlo G, Mascolo N, Izzo AA, Capasso F. Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sciences. 1999; 65(4): 337-53.
  • Monga V, Goyal K, Steindel M, Malhotra M, Rajani DP, Rajani SD. Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents. Medicinal Chemistry Research. 2014; 23(4): 2019-32.
  • Singh P, Anand A, Kumar V. Recent developments in biological activities of chalcones: a mini review. European Journal of Medicinal Chemistry. 2014; 85:758-77.
  • Singh PP, Jayalakshmi B, Kumar NS. Synthesis, Characterization and Antimicrobial Evaluation of Some New Chalcones. Asian Journal of Research in Chemistry. 2013;6(12):1133-6.
  • Dawane BS, Shaikh BM, Khandare NT, Mandawad GG, Chobe SS, Konda SG. Synthesis of Some Novel Substituted Pyrazole Based Chalcones and Their In-Vitro Antimicrobial Activity. Asian Journal of Research in Chemistry. 2010;3(1):90-3.
  • Beena KP, Rajesh P, Nathiya S. Synthesis of some novel substituted isoxazoline based chalcones and their in-vitro antimicrobial activity. Asian Journal of Research in Chemistry. 2010;3(4):1080-2.
  • Parveen P, Usha P, Naik VV, Sultana SS, Ramya MG. Synthesis of Chalcones and Evaluation of Their Anti-Microbial Activity. Research Journal of Pharmaceutical Dosage Forms and Technology. 2014;6(1):26.
  • Rao GE, Rahaman SA, Rani AP, Rao CM. Synthesis, Characterization and Antimicrobial Activity of Novel Chalcones from 1-[4-(1H-imidazol-1-yl) Phenyl] Ethanone. Asian Journal of Research in Chemistry. 2013;6(7):7.
  • Sharma VP, Kumar R. Synthesis, Characterization and Antimicrobial Screening of Some Novel Chromonyl Chalcones. Asian Journal of Research in Chemistry. 2014;7(7):649-52.
  • Lunkad AS, Kothawade SN, Jadhav DV, Chaudhari PS, Bornare SP. Synthesis and Antimicrobial Activity of Some New Chalcones Containing Benzofuran and Benzofuran Schiff Bases. Research Journal of Pharmacy and Technology. 2015;8(3):276.
  • Kumar P, Kumar A, D'Souza S. Synthesis and Antimicrobial Evaluation of Different Substituted Phenylpropenone Pyrrolyl Chalcones. Research Journal of Pharmacy and Technology. 2017;10(5):1426-8.
  • Baviskar B, Patel S, Baviskar B, Khadabadi SS, Shiradkar M. Design and synthesis of some novel chalcones as potent antimicrobial agent. Asian Journal of Research in Chemistry. 2008;(2):67-9.
  • Polo E, Ibarra-Arellano N, Prent-Peñaloza L, Morales-Bayuelo A, Henao J, Galdámez A, Gutiérrez M. Ultrasound-assisted synthesis of novel chalcone, heterochalcone and bis-chalcone derivatives and the evaluation of their antioxidant properties and as acetylcholinesterase inhibitors. Bioorganic Chemistry. 2019; 90:103034.
  • Pola S, Banoth KK, Sankaranarayanan M, Ummani R, Garlapati A. Design, synthesis, in silico studies, and evaluation of novel chalcones and their pyrazoline derivatives for antibacterial and antitubercular activities. Medicinal Chemistry Research. 2020;(10):1819-35.
  • de Mello MV, de Azevedo Abrahim-Vieira B, Domingos TF, de Jesus JB, de Sousa AC, Rodrigues CR, de Souza AM. A comprehensive review of chalcone derivatives as antileishmanial agents. European Journal of Medicinal Chemistry. 2018;150:920- 9.
  • Maguire CJ, Carlson GJ, Ford JW, Strecker TE, Hamel E, Trawick ML, Pinney KG. Synthesis and biological evaluation of structurally diverse α-conformationally restricted chalcones and related analogues. Medicinal Chemistry Communications. 2019;10(8):1445-56.
  • Sharma A, Anghore D, Awasthi R, Kosey S, Jindal S, Gupta N, Raj D, Sood R. A Review on Current Carbon Nanomaterials and Other Nanoparticles Technology and Their Applications in Biomedicine. World Journal of Pharmacy and Pharmaceutical Science. 2015;4(12):1088-113.
  • Shukla P, Satyanarayana M, Verma PC, Tiwari J, Dwivedi AP, Srivastava R, Rehuja N, Srivastava SP, Gautam S, Tamrakar AK, Dwivedi AK. Chalcone-based aryloxypropanolamine as a potential antidiabetic and antidyslipidaemic agent. Current Science. 2017:1675-89.
  • Mahapatra DK, Shivhare RS, Kumar P. Murrayanine-chalcone transformed into novel pyrimidine compounds demonstrated promising anti-inflammatory activity. Asian Journal of Pharmaceutical Research. 2018;8(1):6-10.
  • Lin YM, Zhou Y, Flavin MT, Zhou LM, Nie W, Chen FC. Chalcones and flavonoids as anti-tuberculosis agents. Bioorganic and Medicinal Chemistry. 2002;10(8):2795-802.
  • Heim KE, Tagliaferro AR, Bobilya DJ. Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. The Journal of Nutritional Biochemistry. 2002;13(10):572-84.
  • Kakati D, Sarma JC. Microwave assisted solvent free synthesis of 1, 3-diphenylpropenones. Chemistry Central Journal. 2011;5(1):1- 5.and nonprenylated chalcones and flavanones in vitro. Journal of Agricultural and Food Chemistry. 2000;48(9):3876-84.
  • Ni L, Meng CQ, Sikorski JA. Recent advances in therapeutic chalcones. Expert Opinion on Therapeutic Patents. 2004; 14(12): 1669-91.
  • Downs LE, Wolfe DM, Schreiner PR. Organic Base‐Mediated Condensation of Pyridinecarboxaldehydes to Azachalcones. Advanced Synthesis and Catalysis. 2005;347(2‐3):235-8.
  • Prakash O, Kumar A, Sadana A, Prakash R, Singh SP, Claramunt RM, Sanz D, Alkorta I, Elguero J. Study of the reaction of chalcone analogs of dehydroacetic acid and o-aminothiophenol: synthesis and structure of 1, 5-benzothiazepines and 1, 4-benzothiazines. Tetrahedron. 2005;61(27):6642-51.
  • Prasad YR, Rao AL, Prasoona L, Murali K, Kumar PR. Synthesis and antidepressant activity of some 1, 3, 5-triphenyl-2-pyrazolines and 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines. Bioorganic and Medicinal Chemistry Letters. 2005;15(22):5030-4.
  • 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 antiligase and antiproliferative agents. European Journal of Medicinal Chemistry. 2018;143:1981-96.
  • Goyal K, Kaur R, Goyal A, Awasthi R. Chalcones: A review on synthesis and pharmacological activities. Journal of Applied Pharmaceutical Science. 2021;1 (Supp 1):001–014.
  • Gaonkar SL, Vignesh UN. Synthesis and pharmacological properties of chalcones: a review. Research on Chemical Intermediates. 2017;43(11):6043-77.
  • Smith HE, Paulson MC. The Preparation of Chalcones from Hydroxy and Methoxy Aldehydes and Ketones1. Journal of the American Chemical Society. 1954;76(17):4486-7.
  • Palaniandavar M, Natarajan C. Cobalt (II), nickel (II) and copper (II) complexes of some 2'-hydroxychalcones. Australian Journal of Chemistry. 1980;33(4):737-45.
  • Morrison RT, Boyd RN. Organic Chemistry, 6th edn., Pearson Education Publishers. 2004; 971–990, 997–1020.
  • Eddarir S, Cotelle N, Bakkour Y, Rolando C. An efficient synthesis of chalcones based on the Suzuki reaction. Tetrahedron letters. 2003;44(28):5359-63.
  • Bianco A, Cavarischia C, Farina A, Guiso M, Marra C. A new synthesis of flavonoids via Heck reaction. Tetrahedron letters. 2003;44(51):9107-9.
  • Braun RU, Ansorge M, Müller TJ. Coupling–Isomerization synthesis of chalcones. Chemistry–A European Journal. 2006;12(35):9081-94.
  • Müller TJ, Ansorge M, Aktah D. An Unexpected Coupling–Isomerization Sequence as an Entry to Novel Three‐Component‐Pyrazoline Syntheses. Angewandte Chemie International Edition. 2000;39(7):1253-6.
  • Bora U, Saikia A, Boruah RC. A new protocol for synthesis of alpha, beta-unsaturated ketones using zirconium tetrachloride under microwave irradiation. Indian Journal of Chemistry Section B. 2005;44(12):2523.
  • Ramakrishnan VT, Kagan J. Photochemical conversion of phenyl epoxycinnamate to flavonoids and the synthesis of 2'-hydroxyepoxychalcone. The Journal of Organic Chemistry. 1970;35(9):2898-900.
  • Baba T, Kizuka H, Handa H, Ono Y. Reaction of ketones or aldehydes with 1-alkynes over solid-base catalysts. Applied Catalysis A: General. 2000; 194:203-11.
  • Burmaoglu S, Algul O, Anıl DA, Gobek A, Duran GG, Ersan RH, Duran N. Synthesis and anti-proliferative activity of fluoro-substituted chalcones. Bioorganic and Medicinal Chemistry Letters. 2016;26(13):3172-6.
  • Passalacqua TG, Dutra LA, de Almeida L, Velásquez AM, Torres FA, Yamasaki PR, dos Santos MB, Regasini LO, Michels PA, da Silva Bolzani V, Graminha MA. Synthesis and evaluation of novel prenylated chalcone derivatives as anti-leishmanial and anti-trypanosomal compounds. Bioorganic and Medicinal Chemistry Letters. 2015;25(16):3342-5.
  • Cheng MS, Li RS, Kenyon G. A solid phase synthesis of chalcones by Claisen-Schmidt condensations. Chinese Chemical Letters. 2000;11(10):851-4.
  • Watanabe KI, Imazawa A. Aldol condensations catalyzed by Co (II) complexes of pyridine-containing copolymers. Bulletin of the Chemical Society of Japan. 1982;55(10):3208-11.
  • Rammohan A, Reddy JS, Sravya G, Rao CN, Zyryanov GV. Chalcone synthesis, properties and medicinal applications: a review. Environmental Chemistry Letters. 2020;18(2):433-58.
  • Ananthnag GS, Adhikari A, Balakrishna MS. Iron-catalyzed aerobic oxidative aromatization of 1, 3, 5-trisubstituted pyrazolines. Catalysis Communications. 2014;43:240-3.
  • Zhang Z, Wang Y, Wang M, Lu J, Zhang C, Li L, Jiang J, Wang F. The cascade synthesis of α, β-unsaturated ketones via oxidative C–C coupling of ketones and primary alcohols over a ceria catalyst. Catalysis Science and Technology. 2016;6(6):1693-700.
  • Jagdale AR, Sudalai A. p-Toluenesulfonic acid mediated hydroarylation of cinnamic acids with anisoles and phenols under metal and solvent-free conditions. Tetrahedron Letters. 2007;48(28):4895-8.
  • Schramm OG, Mueller TJ. Microwave‐Accelerated Coupling‐Isomerization Reaction (MACIR)–A General Coupling‐Isomerization Synthesis of 1, 3‐Diarylprop‐2‐en‐1‐ones. Advanced Synthesis and Catalysis. 2006;348(18):2565-70.
  • Mistry RN, Desai KR. Microwave Studies on Synthesis of Some New Heterocyclic Chalcone and Pyrimidine-2-thione Derivatives and Their Antibacterial Activity. Asian Journal of Chemistry. 2004;16(1):201.
  • Gall EL, Texier-Boullet F, Hamelin J. Simple access to α, β unsaturated ketones by acid-catalyzed solvent-free reactions. Synthetic Communications. 1999;29(20):3651-7.
  • Baviskar BA, Baviskar B, Shiradkar MR, Deokate UA, Khadabadi SS. Synthesis and Antimicrobial Activity of Some Novel Benzimidazolyl Chalcones. E-Journal of Chemistry. 2009; 6(1): 196-200.
  • Prasad YR, Kumar PP, Kumar PR, Rao AS. Synthesis and antimicrobial activity of some new chalcones of 2-acetyl pyridine. E-Journal of Chemistry. 2008;5(1):144-8.
  • Rathore MM, Rajput PR, Parhate VV. Synthesis and antimicrobial activity of some chalcones and flavones. International Journal of Chemical and Physical Sciences. 2015; 4:473-77.
  • Rajput SS, Sayyed RA. Synthesis and Evaluation of Antimicrobial Activity of Some Novel Chalcones of 2, 6-Dichloro-4-Trifluoro Methyl Aniline. Heterocyclic Letters. 2017;7(2):333-9.
  • Özdemir A, Altıntop MD, Sever B, Gençer HK, Kapkaç HA, Atlı Ö, Baysal M. A new series of pyrrole-based chalcones: synthesis and evaluation of antimicrobial activity, cytotoxicity, and genotoxicity. Molecules. 2017;22(12):2112.
  • Lal K, Yadav P, Kumar A, Kumar A, Paul AK. Design, synthesis, characterization, antimicrobial evaluation and molecular modeling studies of some dehydroacetic acid-chalcone-1, 2, 3-triazole hybrids. Bioorganic Chemistry. 2018; 77:236-44.
  • Kalaiselvi E, Arunadevi R, Sashikala S. Synthesis, Characterization and Antimicrobial Activity of a Chalcone Derivative. Journal of Science and Technology. 2020;5(4):335-43.
  • Radwan MA, Alshubramy MA, Abdel-Motaal M, Hemdan BA, El-Kady DS. Synthesis, molecular docking and antimicrobial activity of new fused pyrimidine and pyridine derivatives. Bioorganic Chemistry. 2020; 96:103516.
  • da Silva PT, da Cunha Xavier J, Freitas TS, Oliveira MM, Coutinho HD, Leal AL, Barreto HM, Bandeira PN, Nogueira CE, Sena Jr DM, Almeida-Neto FW. Synthesis, spectroscopic characterization and antibacterial evaluation by chalcones derived of acetophenone isolated from Croton anisodontus Müll. Arg. Journal of Molecular Structure. 2021; 1226:129403.
  • Kumar CS, Loh WS, Ooi CW, Quah CK, Fun HK. Structural correlation of some heterocyclic chalcone analogues and evaluation of their antioxidant potential. Molecules. 2013;18(10):11996-2011.
  • Murti Y, Goswam A, Mishra P. Synthesis and antioxidant activity of some chalcones and flavanoids. International Journal of PharmTech Research. 2013; 5:811-8.
  • Miranda CL, Stevens JF, Ivanov V, McCall M, Frei B, Deinzer ML, Buhler DR. Antioxidant and prooxidant actions of prenylated
  • Lahsasni SA, Al Korbi FH, Aljaber NA. Synthesis, characterization and evaluation of antioxidant activities of some novel chalcones analogues. Chemistry Central Journal. 2014;8(1):1-10.
  • Aly MR, Fodah HH, Saleh SY. Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes. European Journal of Medicinal Chemistry. 2014;76:517-30.
  • Sivakumar PM, Prabhakar PK, Doble M. Synthesis, antioxidant evaluation, and quantitative structure–activity relationship studies of chalcones. Medicinal Chemistry Research. 2011;20(4):482-92.
  • Qian YP, Shang YJ, Teng QF, Chang J, Fan GJ, Wei X, Li RR, Li HP, Yao XJ, Dai F, Zhou B. Hydroxychalcones as potent antioxidants: structure–activity relationship analysis and mechanism considerations. Food chemistry. 2011;126(1):241-8.
  • Akhtar MS, Rehman AU, Arshad H, Malik A, Fatima M, Tabassum T, Raza AR, Bukhsh M, Murtaza MA, Mehmood MH, Sultan A. In Vitro Antioxidant Activities and the Therapeutic Potential of Some Newly Synthesized Chalcones Against 4-Acetaminophenol Induced Hepatotoxicity in Rats. Dose-Response. 2021;19(1):1559325821996955.

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  • A Laconic Review on Chalcones: Synthesis, Antimicrobial and Antioxidant activities

Abstract Views: 106  |  PDF Views: 0

Authors

Vishal Kaundal
1Department of Pharmaceutical Analysis and Quality Assurance, Laureate Institute of Pharmacy, Kathog, H.P., India, India
Dheeraj Singh
1Department of Pharmaceutical Analysis and Quality Assurance, Laureate Institute of Pharmacy, Kathog, H.P., India, India
Vipasha
Department of Pharmacology, Maharaja Ranjit Singh Punjab Technical University, Bathinda, Punjab, India., India
Arti Devi
Department of Pharmaceutical Analysis and Quality Assurance, Laureate Institute of Pharmacy, Kathog, H.P., India, India
Shammy Jindal
Department of Pharmaceutics, Laureate Institute of Pharmacy, Kathog, H.P., India, India
Amar Deep Ankalgi
Department of Pharmaceutical Analysis and Quality Assurance, Laureate Institute of Pharmacy, Kathog, H.P., India., India
Kamya Goyal
Department of Pharmaceutical Analysis and Quality Assurance, Laureate Institute of Pharmacy, Kathog, H.P., India., India

Abstract


Chalcones and their derivatives have been an area of great interest for several researchers in recent years. Several number of research publications have been published and chalcones continue to show promising effect for novel drug investigations. Chalcone is an advantaged moiety with therapeutic importance as it comprises of receptive ketoethylenic moiety – CO–CH=CH– having a place with flavonoids. Chalcones (1, 3-Diphenyl-prop-2-en-1-one) consists of a three carbon α, β-unsaturated carbonyl system and two or more aromatic rings and acts as precursors for the biosynthesis of flavonoids in plants. The presence of a highly reactive α, β-unsaturated carbonyl system in chalcone and its derivatives is the justification for its pharmacological potencies. However, synthesis in laboratory of broad range of chalcones has also been reported. Chalcones show a wide range of pharmacological impacts like anthelmintic, antileishmanial, antifungal, antimalarial, antioxidant, antiviral, antibacterial, antiulcer, antimycobacterial, insecticidal, antigout, antihistaminic, antiprotozoal, insecticidal, anticancer, antidiabetic, anti-inflammatory, analgesic etc. Chalcones can be synthesized through Claisen–Schmidt's condensation, Heck's reaction, Aldol condensation reaction, Suzuki's reaction, from cinnamic acid, Sonogashira Isomerization Coupling reaction, Microwave assisted synthesis etc. The purpose of the present review is to centralize the various and widely employed methods of synthesis of chalcone and their various derivatives and their antimicrobial and antioxidant activities.

Keywords


Chalcones, Antimicrobial activity, Antioxidant activity, Claisen–Schmidt condensation, Microwave assisted synthesis.

References