In-vitro Antimicrobial Activity of Novel Quinazoline Derivatives: One-Pot Synthesis and Characterization
Abstract
Designing an efficient class of novel antimicrobial agents becomes an enormous task in pharmaceuticals research and development. Current research work comprised of finding a novel series of various substituted quinazoline derivatives. The synthetic scheme involves single-step, one-pot synthesis involving the condensation of highly activated aromatic amide starting materials with weakly nucleophilic alkyl nitriles to directly provide the corresponding quinazoline derivatives employing trifluoromethanesulfonic anhydride catalyst. All the synthesized compounds were characterized by IR, proton nuclear magnetic resonance (1HNMR) and message, audience, situation, significance (MASS) spectral methods and screened for antimicrobial activity against four bacterial strains Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and two fungal strains Aspergillus niger and Candida albicans. All the compounds displayed decent antimicrobial profile when compared with the standard drugs neomycin and nystatin. Among the synthesized compounds (3a1-3a5&3b1-3b5) evaluated, compounds 3a1, 3a2, 3a3, 3b1and 3b2 have demonstrated decent antimicrobial activity against selected strains of bacteria and fungi.
Keywords:
Quinazolines, One-pot synthesis, Anti-bacterial activity, Antifungal activity, Agar disk diffusion.DOI
https://doi.org/10.25004/IJPSDR.2021.130603References
Zaman SB, Hussain MA, Nye R, Mehta V, Mamun KT, Hossain N. A Review on Antibiotic Resistance: Alarm Bells are Ringing. Cureus. 2017;9(6):1403-1409.
Ventola CL. The antibiotic resistance crisis: part 1: causes and threats. P&T. 2015;40(4):277-283.
Hutchings M, Truman A, Wilkinson B. Antibiotics: Past, present and future. Curr Opin Microbiol. 2019;51:72–80.
Michael CA, Dominey-Howes D, Labbate M. The antibiotic resistance crisis: causes, consequences, and management. Front Public Health. 2014;2:145-157.
Selvam TP, Kumar PV. Quinazoline Marketed drugs - A Review. Res Pharm. 2011;1:1-21.
Abida, Parvez N, Rana A, Imran M. An updated review: newer quinazoline derivatives under clinical trial. Int J Pharm Biol Arch. 2011;2:1651-1657.
Asif M. Chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives. Int J Med Chem.2014;18:395-397.
Rakesh KP, Manukumar HM, Gowda DC. Schif f ’s bases of quinazolinone derivatives: synthesis and SAR studies of a novel series of potential anti-inflammatory and antioxidants. Bio org Med Chem Lett. 2015;25:1072-1077.
Hu J, Zhang Y, Dong L, Wang Z, Chen L, Liang D, Shi D, Shan X, Liang G. Design, synthesis, and biological evaluation of novel quinazoline derivatives as anti-inflammatory agents against lipopolysaccharide-induced acute lung injury in rats. Chem Biol Drug Des. 2015;85:672-684.
Ugale VG, Bari SB.Quinazolines: new horizons in anticonvulsant therapy. Eur J Med Chem. 2014;80:447-501.
Selvam TP, Sivakumar A, Prabhu PP. Design and synthesis of quinazoline carboxylates against Gram-positive, Gram-negative, fungal pathogenic strains, and Mycobacterium tuberculosis. J Pharm Bio Allied Sci. 2014;6:278-284.
Ji Q, Yang D, Wang X, Chen C, Deng Q, Ge Z, Yuan L, Yang X, Liao F. Design, synthesis and evaluation of novel quinazoline-2,4-dione derivatives as chitin synthase inhibitors and antifungal agents. Bio org Med Chem. 2014;22:3405-3413.
Jafari E, Khajouei MR, Hassanzadeh F, Hakimelahi GH, Khodarahmi GA. Quinazolinone and quinazoline derivatives: Recent structures with potent antimicrobial and cytotoxic activities. Res Pharm Sci. 2016;11:1-14.
Al-Salahi R, Abuelizz HA, Ghabbour HA, El-Dib R, Marzouk M. Molecular docking study and antiviral evaluation of 2-thioxo-benzo [g] quinazolin-4 (3 H)-one derivatives. Chemistry Central Journal. 2016 Dec;10(1):1-7.
Wan Z, Hu D, Li P, Xie D, Gan X. Synthesis, antiviral bioactivity of novel 4-thioquinazoline derivatives containing chalcone moiety. Molecules. 2015 Jul;20(7):11861-11874.
Ravez S, Castillo-Aguilera O, Depreux P, Goossens L. Quinazoline derivatives as anticancer drugs: a patent review (2011–present). Expert opinion on therapeutic patents. 2015 Jul 3;25(7):789-804.
Mehndiratta S, Sapra S, Singh M, Nepali K. Quinazolines as apoptosis inducers and inhibitors: A review of patent literature. Recent patents on anti-cancer drug discovery. 2016 Feb 1;11(1):2-66.
Phipps AM, Hume DN. General purpose low temperature dry-ice baths. J Chem Edu. 1968;45(10):664-668.
Movassaghi M, Hill MD. Single-step synthesis of pyrimidine derivatives. J American Chem. Soci. 2006; 128(44):14254-14255.
Khyade MS, Vaikos NP. Comparative phytochemical and antibacterial studies on the bark of Wrightia tinctoria and Wrightia arborea. Int J Pharm Bio Sci. 2011;2(1):176-181.
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