A Review on Chalcones Synthesis and their Biological Activity

  • Shipra Verma Mahatma Gandhi P. G. College
  • Alok Kumar Srivastava Mahatma Gandhi P. G. College
  • O.P. Pandey D.D.U. Gorakhpur University
Keywords: Chalcones, synthesis, biological activity

Abstract

Chalcones are a valuable molecule of medicinal importance due to presence of reactive ketoethylenic group –CO–CH=CH–, belonging to the flavonoid family. These reactive α,β-unsatutated keto function in chalcones are  responsible for their biological activity. Chalcone can be synthesized by several methods using aldehydes and ketones as starting material. This review is focused about different methods of synthesis and versatile biological activity of chalcones including antimicrobial, anticancer, antioxidant, antimalarial, antituberculosis etc.

Author Biographies

Shipra Verma, Mahatma Gandhi P. G. College

Department of Chemistry,
Mahatma Gandhi P. G. College, Gorakhpur,
U. P., India

Alok Kumar Srivastava, Mahatma Gandhi P. G. College

Department of Chemistry,
Mahatma Gandhi P. G. College, Gorakhpur,
U. P., India

O.P. Pandey, D.D.U. Gorakhpur University

Department of Chemistry,
D.D.U. Gorakhpur University, Gorakhpur,
U.P., India

References

1. Avila-Villarreal, G.; Hernández-Abreu, O.; Hidalgo-Figueroa, S.; Navarrete-Vázquez, G.; Escalante-Erosa, F.; Pe˜na-Rodríguez, L.M.; Villalobos-Molina, R.; Estrada-Soto, S. (2013), “Antihypertensive and vasorelaxant effects of dihydrospinochalcone-Aisolated from Lonchocarpus xuul Lundell by NO production:Computational and ex vivo approaches”, Phytomedicine, (20), 1241-1246.
2. Barot, V.M.; Gandhi, S. A.; Mahato, A.; Mehta, N.B. (2013), “Synthesis, X-ray diffraction study and Antimicrobial study of1-(4-butoxy-2-hydroxyphenyl)-3-(2,5-dimethoxyphenyl) prop-2-en-1-one”, International Journal of Scientific and Research Publications, (3).
3. Belsare, D.P.; Pal, S.C.; Kazi, A.A.; Kankate, R.S.V.; Anjari S.S. (2010), “Evaluation of Antioxidant Activity of Chalcones and Flavonoids” International Journal of ChemTech Research, (2), 1080-1089.
4. Bhuiyan, M.M.H.; Hossain, M.I.; Mahmud, M.M.; Mohammad, A.A. (2011) “Microwave-assisted Efficient Synthesis of Chalcones as Probes for Antimicrobial Activities”, Chemistry Journal, (01), 21-28.
5. Bukhari, S.N.A.; Butt, A.M.; Amjad, M.W.B. (2013), “Synthesis and evaluation of chalcone analogues based pyrimidines as angiotensinconverting enzyme inhibitors”, Pakistan Journal of Biological Science, 16(21), 1368-1372.
6. Burmaoglu, S.; Algul, O.; Gobek, A.; Aktas, D.A.; Ulger, M.; Erturk, B.G.; Kaplan, E.; Dogen, A.; Aslan, G.(2017), “Design of potent fluoro-substituted chalcones as antimicrobial agents”, Journal Of Enzyme Inhibition And Medicinal Chemistry, 32(1), 490–495.
7. Chaudhary, N.A.; Juyal V. (2011), “Synthesis of chalcone and their derivatives as antimicrobial agents”, International Journal of Pharmacy and Pharmaceutical Sciences; (3).
8. Chen, J.J.; Cheng, M.J.; Shu, C.W.; Sung, P.J. (2017), “A New Chalcone and Antioxidant Constituents of Glycyrrhiza glabra”, Chemistry of Natural Compounds, 53(4), 632-634.
9. Chen, Y.H.; Wang, W.H.; Wang, Y.H.; Lin, Z.Y.; Wen, C.C.; Chern, C.Y. (2013), “Evaluation of the Anti-Inflammatory Effect of Chalcone and Chalcone Analogues in a Zebrafish Model”, Molecules, (18), 2052-2060.
10. Cheng, J.H.; Hung, C.F.; Yang, S.C.; Wangc, J.P.; Wond, S.J.; Lin, C.N. (2008), “Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2’,5’ dialkoxylchalcones as cancer chemopreventive agents”, Bioorganic & Medicinal Chemistry, (16), 7270–7276.
11. Chidan Kumar, C. S.; Loh, W.S.; Ooi ,C.W.; Quah, C.K.; Fun, H.K. (2013), Structural Correlation of Some Heterocyclic Chalcone Analogues and Evaluation of Their Antioxidant Potential”, Molecules, (18), 11996-12011.
12. Davood, A.; Maseud, S. (2013), “Synthesis and Glucosylation of Chalcone-3'-Carboxylic Acids using Glucosyl Donor”, Quest Journal of Research in Pharmaceutical Science, (1), 01-08.
13. Dhivare, R.S.; Rajput, S.S. (2016), “Microwave assisted solvent free synthesis and antifungal evaluation of3, 5-bis-(4-hydroxy-3-methoxybenzylidene)-Nphenylpiperidine- 2, 6-dionederived from N-phenyl glutarimides”, International Journal of ChemTech Research, 9(3), 325-331.
14. Do, T.H.; Nguyen, D.M.; Truong, V.D.; Do, T.H.T.; Le, M.T.; Pham, T.Q.; Thai, K.M.; Tran, T.D. (2016), “Synthesis and Selective Cytotoxic Activities on Rhabdomyosarcoma and Noncancerous Cells of Some Heterocyclic Chalcones”, Molecules, (21), 1-10.
15. Echeverria, C.; Santibanez, J.F.; Donoso-Tauda, O.; Escobar, C.A.; Ramirez-Tagle, R. (2009), “Structural Antitumoral Activity Relationships of Synthetic Chalcones”, International Journal of Molecular Sciences, (10), 221-231.
16. Emayavaramban, M.; Santhi, N.; Gopi, C.; Manivannan, C.; Raguraman, A. (2013), “Synthesis, Characterization and Anti-diabetic activity of 1,3,5-triaryl-2-pyrazolines in acetic acid under Ultrasound Irradiation, International Letters of Chemistry”, Physics and Astronomy, (14), 172-185.
17. Gaur, R.; Yadav, K.S.; Verma, R.K.; Yadav, N.P.; Bhakuni, R.S. (2014), “In Vivo anti-diabetic activity of derivatives of isoliquiritigenin and liquiritigenin”, Phytomedicine, (21), 415-422.
18. Hasan, S.A.; Elias, A.N.; Jwaied, A.H.; Khuodaer, A.R.; Hussain, S.A. (2012), “Synthesis of new fluorinated chalcone derivative with anti-inflammatoryActivity”, International Journal of Pharmacy and Pharmaceutical Sciences, 4(5), 430-434.
19. Jian-Zhang, W.; Chan-Chan, C.; Lai-Lai, S.; Zhan-Kun W.; Shou-Biao, W.; Wu-Lan, Li.; Su-Hua, C.; Rong-Ping, Z.; Pei-Hong, Q. (2014), “Synthetic Chalcones with Potent Antioxidant Ability on H2O2-Induced Apoptosis in PC12 Cells”. International Journal of Molecular Science, (15), 18525-18539.
20. Ketabforoosh, S. H. M. E.; Kheirollahi, A.; Safavi, M.; Esmati, N.; Ardestani, S.K.; Emami, S., Firoozpour, L.; Shafiee, A.; Foroumadi, A. (2014), “Synthesis and Anti-Cancer Activity Evaluation of New Dimethoxylated Chalcone and Flavanone Analogs”, Arch. Pharm. Chem. Life Sci, (347), 1–8.
21. Kotra, V.; Ganapaty, S.; Adapa, S.R. (2010), “Synthesis of a new series of quinolinyl chalcones as anticancer and anti- inflammatory agents”, Indian Journal of Chemistry, (49B), 1109-1116.
22. Kumar, H.; Devaraji, V.; Joshi, R.; Jadhao, M.K.; Ahirkar, P.; Prasath, R.; Bhavanac, P.; Ghosha, S.K. (2015), “Antihypertensive Activity of a Quinoline Appended Chalcone Derivative and its Site Specific Binding Interaction with Relevant Target Carrier Protein”, RSC Advances.
23. Kumar, N.; Chauhan, L.S. (2015), “Synthesis and anticonvulsant activity of some chalcones incorporated hydrazide derivatives”, Journal of Chemical and Pharmaceutical Research, 7(6), 775-780.
24. Marcelo, N.; Gomes, Rodolpho, C.; Braga, Edyta, M.; Grzelak, Bruno, J.; Neves, Muratov, E.; Ma,R. (2017) “QSAR-driven design, synthesis and discovery of potent chalcone derivatives with antitubercular activity”, Medicinal Chemistry.
25. Murti, Y.; Goswami, A.; Mishra, P. (2013), “Synthesis and Antioxidant Activity of Some Chalcones and Flavanoids”, International Journal of PharmTech Research, 5(2): 811-818.
26. Ngameni, B.; Kuete, V.; Ambassa, P.; Justin, K.; Marlyse, M.L.; Tchoukoua, A.; Roy, R.; Ngadjui, B.T.; Tetsuya, M. (2013), “Synthesis and Evaluation of Anticancer Activity of O-allylchalcone Derivatives”, medicinal chemistry, 3(3): 233-237.
27. Pandey, A.K.; Sharma, R.; Purohit, P.; Dwivedi, R.; Chaturvedi, V.; Chauhan, P.M.S. (2016), “Synthesis of pyrido[1,2-a]imidazo-chalcone via 3-component Groebke-Blackburn-Bienayme reaction and their bioevaluation as potent Antituberculosis Agents”, Chemistry & Biology Interface, (6), 290-299.
28. Prasad, Y.R.; Kumar, P.P.; Kumar, P.R.; Rao, A.S. (2008) “Synthesis and Antimicrobial Activity of Some New Chalcones of 2-Acetyl Pyridine”, E-Journal of Chemistry, (5), 144-148.
29. Rajput, S.S.; Sayyed, R.A.M.A. (2017), “Synthesis And Evaluation of Antimicrobial Activity of Some Novel Chalcones of 2, 6-Dichloro-4-Trifluoro Methyl Aniline”, Heterocyclic Letters, 7(2), 333-339.
30. Rathore, M.M.; Rajput, P. R.; Parhate, V.V. (2015), “Synthesis and Antimicrobial Activity of Some Chalcones and Flavones”, International Journal of Chemical and Physical Sciences, (4), 473-477.
31. Sharma,C. S.; Shekhawat, K. S.; Chauhan, C. S.; Kumar, N. (2013), “Synthesis and anticonvulsant activity of some chalcone derivatives”, Journal of Chemical and Pharmaceutical Research, 5(10): 450-454.
32. Shukla, P.; Satyanarayana, M.; Verma, P.C.; Tiwari, J.; Dwivedi, A.P. (2017), “Chalcone-based aryloxypropanolamine as a potential antidiabetic and antidyslipidaemic agent”,Current Science, (112), 1675-1689.
33. Siddiqui, A.A.; Rahman, M.A.; Shaharyar, M.; Mishra, R. (2010), “Synthesis And Anticonvulsant Activity Of Some Substituted 3,5-Diphenyl-2-Pyrazoline-1-Carboxamide Derivatives”, Chemical Sciences Journal, (2010) 1-10.
34. Sirsat, S.B.; Halikar, N.K.; Pund, M.M.; Vartale, S.P. (2012), “Synthesis and biological screening of some novel hetero aryl chalcone and their complexes”, Research journal of pharmaceutical,biological and chemical sciences, (3), 242.
35. Sulistyowaty, M.I.; Nofianti, K.A.; Suzana, B. T. (2014), “In Vitro Antimalarial Activity Of Chalcone And Its Derivatives”, International Journal of Pharmacy and Pharmaceutical Sciences, (6), 669-671.
36. Suvitha, S.; Ibrahim, S.; Abdelwahab., Mohammed Ali, A.M.; Syam, M. (2012), “Synthesis of Chalcones with Anticancer Activities”, Molecules, (17), 6179-6195.
37. Suwito, H.; Jumina, Mustofa, Pudjiastuti P.; Fanani, M.Z.; Kimata-Ariga, Y.; Katahira, R.; Kawakami, T.; Fujiwara, T.; Hase, T.; Sirat, H.M.; Puspaningsih, N.N.T. (2014) “Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase”, Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents”, Molecules, (19), 21473-21488.
38. Tiwari, B.; Pratapwar, A.R.; Tapas, S.R.; Butle Vatkar, B.S. (2010), “Synthesis and Antimicrobial Activity of Some Chalcone Derivatives”, International Journal of ChemTech Research, (2), 499-503.
39. Turkar, S.S.; Rodge, A.H.; Hatnapure, G.D.; Keche, A.P.; Gaikwad, G.S. (2010), “Synthesis and anti-bacterial, anti-fungal activity of some novel chalcone derivatives”, Journal of Chemical and Pharmaceutical Research, 2(5), 348-355.
40. Umaa, K.; Kavithamani, A.; Maida Engels, S.E.; Geetha, G. (2013), “Quantitative structure activity studies on the anti-mycobacterial potentials of certain chalcone derivatives”, International Journal of Research in Organic Chemistry, 3(2), 6-10.
41. Venkataramireddy,V.; Shankaraiah, V.; Rao, A.T.; Kalyani, C.; Narasu, M.L.; Varala, R.; Jayashree, A. (2016) “Synthesis and anti-cancer activity of novel 3- aryl thiophene-2-carbaldehydes and their aryl/heteroaryl chalcone derivatives”, Rasayan journal of Chemistry, 9(1), 31 – 39.
42. Venkatesh, T.; Bodke, Y.D.; Kenchappa, R.; Telkar, S. (2016), “Synthesis, Antimicrobial and Antioxidant Activity of Chalcone Derivatives Containing Thiobarbitone Nucleus”, Medicinal Chemistry, 6(7), 440-448.
43. Wani, Z.A.; Pathania, A.S.; Mahajan, G.; Behl, A.; Mintoo, M.J.; Guru, S.K.; Viswanath, A.; Malik, F.; Kamal, A.; Mondhe, D.M. (2015), “Anticancer activity of a novel quinazolinone-chalcone derivative through cell cycle arrest in pancreatic cancer cell line”, Journal of Solid Tumors, (5), 73-85.
44. Yadav, N.; Dixit, S.K.; Bhattacharya, A.; Mishra, L.C.; Sharma, M.; Awasthi, S.K.; Bhasin V.K. (2012), “Antimalarial Activity of Newly Synthesized Chalcone Derivatives In Vitro”, Chem Biol Drug Des, (80), 340–347.
Published
2018-06-06
How to Cite
[1]
Verma, S., Srivastava, A.K. and Pandey, O. 2018. A Review on Chalcones Synthesis and their Biological Activity. PharmaTutor. 6, 2 (Jun. 2018), 22-39. DOI:https://doi.org/10.29161/PT.v6.i2.2018.22.
Section
Articles