Synthesis, Characterization and Biological Evaluation of Newer Chalcones by Microwave irradiation
Keywords:Pyridazine, Microwave, Chalcones, Antifungal, Antibacterial, Acetophenone
Chalcones are a common natural pigment & one of the most important classes of flavonoids & iso-flavonoids across the whole edible plant kingdom. This α, β- unsaturated carbonyl is an important and versatile intermediate for the preparation of various heterocycles. Their utility lies in their usefulness as synthons. Many research articles on chalcones were found in the literature. In this article, a series of pyridazine Chalcone derivatives were synthesized by Claisen-Schmidt condensation of 6-(3-Acetyl phenylamino) pyridazin-3(2H)-one with substituted benzaldehyde with potassium hydroxide in microwave assessed irradiation. All the synthesized derivatives(3a-o) were screened for their anti-bacterial and anti-fungal activities. Several compounds throughout the series showed moderate to good anti-bacterial and anti-fungal activity against human pathogens.
Sahu N. K., Balbhadra S. S., Choudhary J., Kohli D. V. Exploring Pharmacological significance of chalcone scaffold: A review. Curr. Med. Chem. 2012; 19:209-225. Doi:10.2174/092986712803414132 PMid:22320299
A. R. Kartizsky, A. F. Pozharskii (Hand book of heterocyclic Chemistry-II-edition) Pergamon press; New York, 2000.
D. N. Dhar, V. P. Gupta, J. Ind. Chem. Soc., 1971, 9, 818., Dhar, D. N., The Chemistry of chalcones & related compounds, edited by (John Wiley & Sons, New York) 1951.
Salman A. Khan, Abdullah M. Asiri, Green synthesis, characterization and biological evaluation of novel chalcones as antibacterial agents, Arabian Journal of Chemistry, 2017, 10, S2890-2895. (2893), DOI: 10.1016/j.arabjc.2013.11.018.
J. F. Ballesteros, M. J. Sanz, M. A. Miranda, S. Iborra M. Paya, M. J. Alcarz Synthesis and Pharmacological Evaluation of 2’-Hydroxychalcones and Flavones as Inhibitors of Inflammatory Mediators Generation, J. Med. Chem., 1995, 38, 14, 2794-2797. https://doi.org/10.1021/jm00014a032
Nilesh L. Jadhav, Aniruddha B. Pandit, Dipak V. Pinjari, Green Approach for synthesis of Chalcones (3- (4-flurophenyl)-1- (4-Methoxyphenyl) prop-2-en—1-one) using concentrated solar radiation, Solar Energy 147 (2017)232-239 .https://doi.org/10.1016/j. solener. 2017. 03. 047.
Marina Ritter, Rosiane M. Martins, Silnana, Rosa, Juliana L. Malavolta, Rafael G. Lund, Alex F. C. Flores, Claudio M. P. Pereira, Green Synthesis of Chalcones & Microbiological Evaluation, J. Braz. Chem. Soc., Vol. 26, No. 6, 1201-1210,2015, Printed in Brazil - © 2015 Sociedade Brasileira de Química 0103 - 5053 $6.00+0.00.
S. Zangade, S. Mokle, A. Vibhute, Y. Vibhute, An efficient and Operationally Simple Synthesis of Some New Chalcones By using Grinding Technique, Chemical Science Journal, 2011, Vol. 2011: CSJ-13 1, E-ISSN: 21503494. DOI: 10.4172/2150-3494.1000011.
Rajendra Sandipan Shinde, Satish Ashruba Dake,, Rajendra Pundalikrao Pawar, Design, Synthesis and Antimicrobial Activity of Some Triazine Chalcone Derivatives; Anti-Infective Agents, 2019,17,17. DOI:10.2174/22113525176661907101151111. Hijova E., Bioavailability of Chalcones, Bratisl Lek Listy, 2006,107: 80-84.
Pawan kumar Padarthi & Elangovan Namasivayam, Synthesis and Biological evaluation of Chalcones from 2-Acetyl-5- Methyl furan, International Journal of Pharmaceutical Science and Research, 2013; Vol. 4(7); 2629-2638. https://doi.org/10.13040/IJPSR.0975-8232.4(7).2629-38
Mohammed Rayees Ahmada, V. Girija Sastrya, Nasreen Banob, Syed, Synthesis of novel chalcone derivatives by conventional and microwave irradiation method and their pharmacological activities, Arabian Journal of Chemistry 2016, Vol.9 S931-S935. https://doi.org/10.1016/j.arabjc.2011.09.002 .
Shrikrishna. D. Tupare, Santosh V. Nalage, Sharad R. Bobe, Shivshankar N. Hallale, Sheshanath V. Bhosale, Sanjay K. Vyawahare, Satish A. Dake, Sidhanath V. Bhosale and Rajendra P. Pawar, “Revisit: Eaton’s Reagent Catalyzed Synthesis of Mono and Bis-Chalcone Derivatives”, Letters in Organic Chemistry (2012) 9: 526. https://doi.org/10.2174/157017812802139627
Liu M, Wilairat P, Mei-L in G, 2001. Antimalarial aloxylated and hydroxylated chalcones: structure activity relationship analysis. Journal of Medicinal Chemistry.44: 4443-4452.
Opletalova V, 2000. Chalcones and their heterocyclic analogues as potential therapeutic agents of bacterial diseases. Ceska Slov Farm, 49: 278-284.
Lee SH, Nan JX, Zhao YZ, Woo SW, Park EJ, Kang TH, Seo GS, Kim YC, Sohn DH, 2003. The Chalcones Butein from Rhus verniciflua shows antifibrogenic activity. Planta, 69: 990-994.
Konieczny MT, Konieczny W, Sabisz M, Skladanowski A, Wakiec R, Augusttynowiczkopec E, Zwolska Z, 2007. Synthesis of isomeric, oxathiolone fused chalcones and comparison, their activity towards various microorganisms and human cancer cell lines. Chemical and Pharmaceutical Bulletin, 55: 817-820.
Oyedapo AO, Mankanju VO, Adewunmi CO, Iwalewa EO, Adenowo TK, 2004. Antitrichomonal activity of 1,3 diaryl-2-propen-1- one on Trichomona gallinae. African Journal of Traditional, Complementary and Alternative Medicines, 1: 55-62.
Jin F, Jin YL, Sohn DW, Kim S-A, Sohn DH, Kim YC, Kim HS, 2007. Structural requirements of 2’,4’,6’ Tris (methoxy methoxy) chalcones derivatives for anti-inflammatory activity. Archives of Pharmacal Research, 30: 1359-1367.
Narender T, Khaliq T, Shewata, Nishi, Goyal N, Gupta S., Synthesis of chromen chalcones and evaluation of their in vitro antileishmanial activity. Bioorganic and Medicinal Chemistry, , 2005, 13: 6543-6550.
Aponte J C, Verastegui M, Malaga E, Zimic M, Quiliano M, Vaisberg AJ, Gilman RH, Hammond GB, 2008. Synthesis, cytotoxicity and anti-Trypanosoma cruzi activity of new chalcones. Journal of Medicinal Chemistry, 51: 6230-6234.
Asiri, A. M. Khan, S. A., Marwani, H. M., Sharma, K.,. Synthesis, Spectroscopic and Physicochemical investigation of environmentally benign heterocyclic Schiff base derivatives as antibacterial agents on the bases of in vitro and density functional theory. J. photochem, photobiol., 2013, B120,82-89.
R. J. Grayer and J. B. Harborne, “A Survey of Antifungal Compounds from Higher Plants,” Phytochemistry, Vol. 37, No. 1, 1994, pp.19-42. Doi:10.1016/0031-9422(94)85005-4
O. N. Irob, M. Moo-Young and W. A. Anderson, “Antimicrobial Activity of Annatto Extract,” International Journal of Pharmaceutics, Vol. 34, No. 2,1996, pp.87-90. Doi:10.1076/phbi.184.108.40.20601.
How to Cite
Copyright (c) 2020 Shrikrishna Tupare, Rajendra P. Pawar
This work is licensed under a Creative Commons Attribution 4.0 International License.