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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Mini-Review Article

Recent Progress in Environmentally-Friendly Methods for Chalcone Synthesis

Author(s): Jeky C. Makwana, Ranjitsinh C. Dabhi, Pranav S. Shrivastav and Jayesh J. Maru*

Volume 21, Issue 1, 2024

Published on: 29 August, 2023

Page: [29 - 39] Pages: 11

DOI: 10.2174/1570178620666230713154616

Price: $65

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Abstract

Chalcones are important scaffolds in the field of medicinal chemistry due to the presence of α,β-unsaturated ketone functionality. They are usually synthesized by reacting an aldehyde with acetophenone in the presence of acid or base using the Claisen-Schmidt condensation reaction. Numerous chalcone derivatives have been developed due to the simplicity of their synthesis, and they have intriguing biological activity that has clinical implications for a range of disorders. The review article discusses the advancements made since 2005 for the synthesis of chalcones derivatives using environmentally friendly methods such as the use of green catalysts and solvents, ultrasonic radiation, microwave energy, and methodologies involving grinding in the absence of solvents.

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[1]
Di Carlo, G.; Mascolo, N.; Izzo, A.A.; Capasso, F. Life Sci., 1999, 65(4), 337-353.
[http://dx.doi.org/10.1016/S0024-3205(99)00120-4] [PMID: 10421421]
[2]
Xue, C.X.; Cui, S.Y.; Liu, M.C.; Hu, Z.D.; Fan, B.T. Eur. J. Med. Chem., 2004, 39(9), 745-753.
[http://dx.doi.org/10.1016/j.ejmech.2004.05.009] [PMID: 15337287]
[3]
Sivakumar, P.M.; Geetha Babu, S.K.; Mukesh, D. Chem. Pharm. Bull. (Tokyo), 2007, 55(1), 44-49.
[http://dx.doi.org/10.1248/cpb.55.44] [PMID: 17202700]
[4]
Gacche, R.; Khsirsagar, M.; Kamble, S.; Bandgar, B.; Dhole, N.; Shisode, K.; Chaudhari, A. Chem. Pharm. Bull. (Tokyo), 2008, 56(7), 897-901.
[http://dx.doi.org/10.1248/cpb.56.897] [PMID: 18591798]
[5]
Bello, M.L.; Chiaradia, L.D.; Dias, L.R.S.; Pacheco, L.K.; Stumpf, T.R.; Mascarello, A.; Steindel, M.; Yunes, R.A.; Castro, H.C.; Nunes, R.J.; Rodrigues, C.R. Bioorg. Med. Chem., 2011, 19(16), 5046-5052.
[http://dx.doi.org/10.1016/j.bmc.2011.06.023] [PMID: 21757358]
[6]
de Oliveira, G.R.; de Oliveira, H.C.B.; Silva, W.A.; da Silva, V.H.C.; Sabino, J.R.; Martins, F.T. Struct. Chem., 2012, 23(6), 1667-1676.
[http://dx.doi.org/10.1007/s11224-012-9972-7]
[7]
Downs, L.E.; Wolfe, D.M.; Schreiner, P.R. Adv. Synth. Catal., 2005, 347(2-3), 235-238.
[http://dx.doi.org/10.1002/adsc.200404318]
[8]
Saleem, F. Kanwal; Khan, K.M.; Chigurupati, S.; Solangi, M.; Nemala, A.R.; Mushtaq, M.; Ul-Haq, Z.; Taha, M.; Perveen, S. Bioorg. Chem., 2021, 106, 104489.
[http://dx.doi.org/10.1016/j.bioorg.2020.104489] [PMID: 33272713]
[9]
Prakash, O.; Kumar, A.; Sadana, A.; Prakash, R.; Singh, S.P.; Claramunt, R.M.; Sanz, D.; Alkorta, I.; Elguero, J. Tetrahedron, 2005, 61(27), 6642-6651.
[http://dx.doi.org/10.1016/j.tet.2005.03.035]
[10]
Prasad, Y.R.; Rao, A.L.; Prasoona, L.; Murali, K.; Kumar, P.R. Bioorg. Med. Chem. Lett., 2005, 15(22), 5030-5034.
[http://dx.doi.org/10.1016/j.bmcl.2005.08.040] [PMID: 16168645]
[11]
Devi, L.; Sharma, G.; Kant, R.; Shukla, S.K.; Rastogi, N. Org. Biomol. Chem., 2021, 19(18), 4132-4136.
[http://dx.doi.org/10.1039/D1OB00274K] [PMID: 33870359]
[12]
Gupta, S.; Maurya, P.; Upadhyay, A.; Kushwaha, P.; Krishna, S.; Siddiqi, M.I.; Sashidhara, K.V.; Banerjee, D. Eur. J. Med. Chem., 2018, 143, 1981-1996.
[http://dx.doi.org/10.1016/j.ejmech.2017.11.015] [PMID: 29146133]
[13]
Zhuang, C.; Zhang, W.; Sheng, C.; Zhang, W.; Xing, C. Miao. Z. Chem. Rev., 2017, 117(12), 7762-7810.
[http://dx.doi.org/10.1021/acs.chemrev.7b00020] [PMID: 28488435]
[14]
Pereira, R.; Silva, A.M.S.; Ribeiro, D.; Silva, V.L.M.; Fernandes, E. Eur. J. Med. Chem., 2023, 252, 115280.
[http://dx.doi.org/10.1016/j.ejmech.2023.115280] [PMID: 36966653]
[15]
Ni, L.; Meng, C.Q.; Sikorski, J.A. Expert Opin. Ther. Pat., 2004, 14(12), 1669-1691.
[http://dx.doi.org/10.1517/13543776.14.12.1669]
[16]
Sahu, K. Curr. Med. Chem., 2012, 19(2), 209-225.
[http://dx.doi.org/10.2174/092986712803414132] [PMID: 22320299]
[17]
Rathore, S.; Mishra, S.; Mahapatra, D.K.; Patil, S.; Patil, A.G. Curr. Bioact. Compd., 2020, 16(6), 747-808.
[http://dx.doi.org/10.2174/1573407215666190411150734]
[18]
Claisen, L.; Claparède, A. Ber. Dtsch. Chem. Ges., 1881, 14(2), 2460-2468.
[http://dx.doi.org/10.1002/cber.188101402192]
[19]
Guida, A.; Lhouty, M.H.; Tichit, D.; Figueras, F.; Geneste, P. Appl. Catal. A Gen., 1997, 164(1-2), 251-264.
[http://dx.doi.org/10.1016/S0926-860X(97)00175-0]
[20]
Nielsen, S.F.; Christensen, S.B.; Cruciani, G.; Kharazmi, A.; Liljefors, T. J. Med. Chem., 1998, 41(24), 4819-4832.
[http://dx.doi.org/10.1021/jm980410m] [PMID: 9822551]
[21]
Jaiswal, P.; Pathak, D.P.; Bansal, H.; Agarwal, U. J. Chem. Pharm. Res., 2018, 10(4), 160-173. [https://www.jocpr.com/articles/chalcone--their-heterocyclic-analogue-a-review-article.pdf
[22]
Climent, M.J.; Corma, A.; Iborra, S.; Primo, J. J. Catal., 1995, 151(1), 60-66.
[http://dx.doi.org/10.1006/jcat.1995.1008]
[23]
Eddarir, S.; Cotelle, N.; Bakkour, Y.; Rolando, C. Tetrahedron Lett., 2003, 44(28), 5359-5363.
[http://dx.doi.org/10.1016/S0040-4039(03)01140-7]
[24]
Kumar, A.; Sharma, S.; Tripathi, V.D.; Srivastava, S. Tetrahedron, 2010, 66(48), 9445-9449.
[http://dx.doi.org/10.1016/j.tet.2010.09.089]
[25]
Nasir Abbas Bukhari, S.; Jasamai, M.; Jantan, I. Mini Rev. Med. Chem., 2012, 12(13), 1394-1403.
[http://dx.doi.org/10.2174/138955712804586648] [PMID: 22876958]
[26]
Boeck, P.; Leal, P.C.; Yunes, R.A.; Filho, V.C.; López, S.; Sortino, M.; Escalante, A.; Furlán, R.L.E.; Zacchino, S. Arch. Pharm. (Weinheim), 2005, 338(2-3), 87-95.
[http://dx.doi.org/10.1002/ardp.200400929] [PMID: 15799012]
[27]
Konduru, N.K.; Dey, S.; Sajid, M.; Owais, M.; Ahmed, N. Eur. J. Med. Chem., 2013, 59, 23-30.
[http://dx.doi.org/10.1016/j.ejmech.2012.09.004] [PMID: 23202847]
[28]
Kucerova-Chlupacova, M.; Kunes, J.; Buchta, V.; Vejsova, M.; Opletalova, V. Molecules, 2015, 20(1), 1104-1117.
[http://dx.doi.org/10.3390/molecules20011104] [PMID: 25587786]
[29]
López, S.N.; Castelli, M.V.; Zacchino, S.A.; Domínguez, J.N.; Lobo, G.; Charris-Charris, J.; Cortés, J.C.G.; Ribas, J.C.; Devia, C.; Rodríguez, A.M.; Enriz, R.D. Bioorg. Med. Chem., 2001, 9(8), 1999-2013.
[http://dx.doi.org/10.1016/S0968-0896(01)00116-X] [PMID: 11504637]
[30]
Go, M.; Wu, X.; Liu, X. Curr. Med. Chem., 2005, 12(4), 483-499.
[http://dx.doi.org/10.2174/0929867053363153] [PMID: 15720256]
[31]
Nowakowska, Z. Eur. J. Med. Chem., 2007, 42(2), 125-137.
[http://dx.doi.org/10.1016/j.ejmech.2006.09.019] [PMID: 17112640]
[32]
Kotra, V.; Ganapaty, S.; Adapa, S.R. Indian J. Chem., 2010, 49B, 1109-1116. nopr.niscpr.res.in/handle/123456789/10082
[33]
Vogel, S.; Ohmayer, S.; Brunner, G.; Heilmann, J. Bioorg. Med. Chem., 2008, 16(8), 4286-4293.
[http://dx.doi.org/10.1016/j.bmc.2008.02.079] [PMID: 18343123]
[34]
Kim, B.T.; Chun, J.C.; Hwang, K.J. Bull. Korean Chem. Soc., 2008, 29(6), 1125-1130.
[http://dx.doi.org/10.5012/bkcs.2008.29.6.1125]
[35]
Kumar, S.K.; Hager, E.; Pettit, C.; Gurulingappa, H.; Davidson, N.E.; Khan, S.R. J. Med. Chem., 2003, 46(14), 2813-2815.
[http://dx.doi.org/10.1021/jm030213+] [PMID: 12825923]
[36]
Leon-Gonzalez. J. Curr. Med. Chem., 2015, 22(30), 3407-3425.
[http://dx.doi.org/10.2174/0929867322666150729114829] [PMID: 26219392]
[37]
Hseu, Y.C.; Chiang, Y.C.; Vudhya Gowrisankar, Y.; Lin, K.Y.; Huang, S.T.; Shrestha, S.; Chang, G.R.; Yang, H.L. Cancers (Basel), 2020, 12(10), 2936.
[http://dx.doi.org/10.3390/cancers12102936] [PMID: 33053749]
[38]
Wan, Z.; Hu, D.; Li, P.; Xie, D.; Gan, X. Molecules, 2015, 20(7), 11861-11874.
[http://dx.doi.org/10.3390/molecules200711861] [PMID: 26132908]
[39]
Marinov, R.; Markova, N.; Krumova, S.; Yotovska, K.; Zaharieva, M.M.; Genova-Kalou, P. Pharmacia, 2020, 67(4), 325-337.
[http://dx.doi.org/10.3897/pharmacia.67.e53842]
[40]
Elkhalifa, D.; Al-Hashimi, I.; Al Moustafa, A.E.; Khalil, A. J. Drug Target., 2021, 29(4), 403-419.
[http://dx.doi.org/10.1080/1061186X.2020.1853759] [PMID: 33232192]
[41]
Bandgar, B.P.; Gawande, S.S. Bioorg. Med. Chem., 2010, 18(5), 2060-2065.
[http://dx.doi.org/10.1016/j.bmc.2009.12.077] [PMID: 20138527]
[42]
Karthikeyan, C.; Moorthy, N.S.; Ramasamy, S.; Vanam, U.; Manivannan, E.; Karunagaran, D.; Trivedi, D. Recent Anti-Cancer Drug Discov, 2015, 10(1), 97-115.
[http://dx.doi.org/10.2174/1574892809666140819153902] [PMID: 25138130]
[43]
Khanapure, S.; Jagadale, M.; Bansode, P.; Choudhari, P.; Rashinkar, G. J. Mol. Struct., 2018, 1173, 142-147.
[http://dx.doi.org/10.1016/j.molstruc.2018.06.091]
[44]
Yang, J.L.; Ma, Y.H.; Li, Y.H.; Zhang, Y.P.; Tian, H.C.; Huang, Y.C.; Li, Y.; Chen, W.; Yang, L.J. ACS Omega, 2019, 4(23), 20381-20393.
[http://dx.doi.org/10.1021/acsomega.9b03077] [PMID: 31815242]
[45]
Chouiter, M.I.; Boulebd, H.; Pereira, D.M.; Valentão, P.; Andrade, P.B.; Belfaitah, A.; Silva, A.M.S. Future Med. Chem., 2020, 12(6), 493-509.
[http://dx.doi.org/10.4155/fmc-2019-0342] [PMID: 32100558]
[46]
Shaik, A.; Bhandare, R.R.; Palleapati, K.; Nissankararao, S.; Kancharlapalli, V.; Shaik, S. Molecules, 2020, 25(5), 1047.
[http://dx.doi.org/10.3390/molecules25051047] [PMID: 32110945]
[47]
Ouyang, Y.; Li, J.; Chen, X.; Fu, X.; Sun, S.; Wu, Q. Biomolecules, 2021, 11(6), 894.
[http://dx.doi.org/10.3390/biom11060894] [PMID: 34208562]
[48]
Lagu, S.B.; Yejella, R.P.; Bhandare, R.R.; Shaik, A.B. Pharmaceuticals (Basel), 2020, 13(11), 375.
[http://dx.doi.org/10.3390/ph13110375] [PMID: 33182305]
[49]
Zheng, C.J.; Jiang, S.M.; Chen, Z.H.; Ye, B.J.; Piao, H.R. Arch. Pharm. (Weinheim), 2011, 344(10), 689-695.
[http://dx.doi.org/10.1002/ardp.201100005] [PMID: 21887800]
[50]
Chu, W.C.; Bai, P.Y.; Yang, Z.Q.; Cui, D.Y.; Hua, Y.G.; Yang, Y.; Yang, Q.Q.; Zhang, E.; Qin, S. Eur. J. Med. Chem., 2018, 143, 905-921.
[http://dx.doi.org/10.1016/j.ejmech.2017.12.009] [PMID: 29227931]
[51]
Tang, Y.L.; Li, Y.K.; Li, M.X.; Gao, H.; Yang, X.B.; Mao, Z.W. Curr. Org. Synth., 2020, 17(2), 136-143.
[http://dx.doi.org/10.2174/1570179417666191227115207] [PMID: 32418516]
[52]
Xu, M.; Wu, P.; Shen, F.; Ji, J.; Rakesh, K.P. Bioorg. Chem., 2019, 91, 103133.
[http://dx.doi.org/10.1016/j.bioorg.2019.103133] [PMID: 31374524]
[53]
Anastas, P.T.; Warner, J.C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
[54]
Anastas, P.T.; Kirchhoff, M.M. Acc. Chem. Res., 2002, 35(9), 686-694.
[http://dx.doi.org/10.1021/ar010065m] [PMID: 12234198]
[55]
Anastas, P.; Eghbali, N. Chem. Soc. Rev., 2010, 39(1), 301-312.
[http://dx.doi.org/10.1039/B918763B] [PMID: 20023854]
[56]
Abdussalam-Mohammed, W.; Ali, A.Q.; Errayes, A.O. Chemical Methodologies, 2020, 4(4), 408-423.
[http://dx.doi.org/10.33945/SAMI/CHEMM.2020.4.4]
[57]
Chauhan, P.; Chimni, S.S. Beilstein J. Org. Chem., 2012, 8(1), 2132-2141.
[http://dx.doi.org/10.3762/bjoc.8.240] [PMID: 23243475]
[58]
Banerjee, M.; Panjikar, P.C.; Das, D.; Iyer, S.; Bhosle, A.A.; Chatterjee, A. Tetrahedron, 2022, 112, 132753.
[http://dx.doi.org/10.1016/j.tet.2022.132753]
[59]
Saini, K.E-J. Chem, 2005, 2(4), 224-227.
[http://dx.doi.org/10.1155/2005/294094]
[60]
Kumar, S.; Lamba, M.S.; Makrandi, J.K. Green Chem. Lett. Rev., 2008, 1(2), 123-125.
[http://dx.doi.org/10.1080/17518250802325993]
[61]
Rateb, N.M.; Zohdi, H.F. Synth. Commun., 2009, 39(15), 2789-2794.
[http://dx.doi.org/10.1080/00397910802664244]
[62]
Mason, T.J.; Vinatoru, M. Sonochemistry: Fundamentals and Evolution; Walter de Gruyter GmbH & Co KG: Berlin, Germany, 2023.
[63]
Bassyouni, F.A.; Abu-Bakr, S.M.; Rehim, M.A. Res. Chem. Intermed., 2012, 38(2), 283-322.
[http://dx.doi.org/10.1007/s11164-011-0348-1]
[64]
Majumder, A.; Gupta, R.; Jain, A. Green Chem. Lett. Rev., 2013, 6(2), 151-182.
[http://dx.doi.org/10.1080/17518253.2012.733032]
[65]
Horikoshi, S.; Serpone, N. Catal. Sci. Technol., 2014, 4(5), 1197-1210.
[http://dx.doi.org/10.1039/c3cy00753g]
[66]
Gadkari, Y.U.; Hatvate, N.T.; Takale, B.S.; Telvekar, V.N. New J. Chem., 2020, 44(20), 8167-8170.
[http://dx.doi.org/10.1039/D0NJ01351J]
[67]
Calvino, V.; Picallo, M.; López-Peinado, A.J.; Martín-Aranda, R.M.; Durán-Valle, C.J. Appl. Surf. Sci., 2006, 252(17), 6071-6074.
[http://dx.doi.org/10.1016/j.apsusc.2005.11.006]
[68]
Asiri, A.M.; Marwani, H.M.; Alamry, K.A.; Al-Amoudi, M.S.; Khan, S.A.; El-Daly, S.A. Int. J. Electrochem. Sci., 2014, 9(2), 799-809.
[69]
Khan, S.A.; Asiri, A.M. Arab. J. Chem., 2017, 10, S2890-S2895.
[http://dx.doi.org/10.1016/j.arabjc.2013.11.018]
[70]
Jadhav, N.L.; Gondhalekar, K.A.; Doltade, S.B.; Pinjari, D.V. Sol. Energy, 2018, 171, 769-773.
[http://dx.doi.org/10.1016/j.solener.2018.07.027]
[71]
Khan, S.A.; Asiri, A.M.; Al-Ghamdi, N.S.M.; Asad, M.; Zayed, M.E.M.; Elroby, S.A.K.; Aqlan, F.M.; Wani, M.Y.; Sharma, K. J. Mol. Struct., 2019, 1190, 77-85.
[http://dx.doi.org/10.1016/j.molstruc.2019.04.046]
[72]
Bhatt, K.; Vishal Rana, V.; Patel, N.; Parikh, J.; Pillai, S. Biointerface Res. Appl. Chem., 2022, 13(2), 130.
[http://dx.doi.org/10.33263/BRIAC132.130]
[73]
Marion, P.; Bernela, B.; Piccirilli, A.; Estrine, B.; Patouillard, N.; Guilbot, J.; Jérôme, F. Green Chem., 2017, 19(21), 4973-4989.
[http://dx.doi.org/10.1039/C7GC02006F]
[74]
Federsel, H.J. Synthesis, 2022, 54(19), 4257-4271.
[http://dx.doi.org/10.1055/a-1752-5471]
[75]
Dabhi, R.C.; Patel, U.P.; Rathod, V.B.; Shah, S.N.; Maru, J.J. Current. Chem. Lett., 2023, 12(1), 133-140.
[http://dx.doi.org/10.5267/j.ccl.2022.8.010]
[76]
Saravanamurugan, S.; Palanichamy, M.; Arabindoo, B.; Murugesan, V. Catal. Commun., 2005, 6(6), 399-403.
[http://dx.doi.org/10.1016/j.catcom.2005.03.005]
[77]
Shen, J.; Wang, H.; Liu, H.; Sun, Y.; Liu, Z. J. Mol. Catal. Chem., 2008, 280(1-2), 24-28.
[http://dx.doi.org/10.1016/j.molcata.2007.10.021]
[78]
Xu, Q.; Yang, Z.; Yin, D.; Zhang, F. Catal. Commun., 2008, 9(7), 1579-1582.
[http://dx.doi.org/10.1016/j.catcom.2008.01.007]
[79]
Tamuly, C.; Saikia, I.; Hazarika, M.; Bordoloi, M.; Hussain, N.; Das, M.R.; Deka, K. RSC Advances, 2015, 5(12), 8604-8608.
[http://dx.doi.org/10.1039/C4RA14225J]
[80]
Yin, H.; Shi, X.; Wang, H.; Liu, G.; Ma, L. Processes (Basel), 2019, 7(4), 236.
[http://dx.doi.org/10.3390/pr7040236]
[81]
Chand, S.; Sandhu, J.S. Indian J. Chem., 2015, 54, 1350-1354. nopr.niscpr.res.in/handle/123456789/33037
[82]
Ghorbani, P.; Nasr-Esfahani, M.; Eftekhari Far, B. Russ. J. Org. Chem., 2022, 58(12), 1812-1820.
[http://dx.doi.org/10.1134/S1070428022120107]
[83]
Cvjetko Bubalo, M. Vidović, S.; Radojčić Redovniković, I.; Jokić,. S. J. Chem. Technol. Biotechnol., 2015, 90(9), 1631-1639.
[http://dx.doi.org/10.1002/jctb.4668]
[84]
Byrne, F.P.; Jin, S.; Paggiola, G.; Petchey, T.H.M.; Clark, J.H.; Farmer, T.J.; Hunt, A.J.; Robert McElroy, C.; Sherwood, J. Sustainable Chemical Processes, 2016, 4(1), 7.
[http://dx.doi.org/10.1186/s40508-016-0051-z]
[85]
Vieira, L.C.C.; Paixão, M.W.; Corrêa, A.G. Tetrahedron Lett., 2012, 53(22), 2715-2718.
[http://dx.doi.org/10.1016/j.tetlet.2012.03.079]
[86]
Ritter, M.; Martins, R.M.; Rosa, S.A.; Malavolta, J.L.; Lund, R.G.; Flores, A.F.C.; Pereira, C.M.P. J. Braz. Chem. Soc., 2015, 26, 1201-1210.
[http://dx.doi.org/10.5935/0103-5053.20150084]
[87]
Suwito, H. Jumina; Mustofa; Suwito, H.; Pudjiastuti, P.; Fanani, M.Z.; Kimata-Ariga, Y.; Katahira, R.; Kawakami, T.; Fujiwara, T.; Hase, T.; Sirat, H.M.; Puspaningsih, N.N. Molecules, 2014, 19(12), 21473-21488.
[http://dx.doi.org/10.3390/molecules191221473] [PMID: 25532844]

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