Synthesis, Characterization and Biological Evaluation of Novel Isoxazolo [5,4-b] Quinolines as potent Antimicrobial Agents
Abstract
In order to combat antimicrobial resistance, antimicrobial chemotherapy made advances in the development of new potent antibiotics and antifungal agents. This is because the microorganisms are becoming resistant to the drugs due to improvements in current antibiotic classes by changing their pore formation mechanism and membrane permeability as well as by adjusting to combat the efficacy of the drugs. In order to address the microbial resistance, a series of novel isoxazolo [5,4-b] quinolines are synthesized and evaluated for antibacterial and antifungal activities. The synthesized compounds 4c, 4f and 4g exhibited potent antibacterial activity, and 4c and 4e revealed moderate antifungal activity.
Keywords:
Quinoline, isoxazole, Antibacterial activity, antifungal activityDOI
https://doi.org/10.25004/IJPSDR.2022.140609References
Olateju OA, Babalola CP, Olubiyi OO, Kotila OA, Kwasi DA, Oaikhena AO, Okeke IN. Quinoline antimalarials increase the antibacterial activity of ampicillin. Front Microbiol. 2021; 12: 556550. https:// doi.org/10.3389/fmicb.2021.556550
Duparc S, Chalon S, Miller S, Richardson N, Toovey S. Neurological and psychiatric safety of tafenoquine in Plasmodium vivax relapse prevention: a review. Malar J. 2020; 19: 111-128. https://doi. org/10.1186/s12936-020-03184-x
Das RR, Jaiswal N, Dev N, Jaiswal N, Naik SS, Sankar J. Efficacy and safety of anti-malarial drugs (chloroquine and Hydroxy-chloroquine) in treatment of COVID-19 infection: A systematic review and meta-analysis. Front Med. 2020; 7: 482-497. https:// doi.org/10.3389/fmed.2020.00482
Sharma V, Mehta DK, Das R. Synthetic methods of quinoline derivatives as potent anticancer agents. Mini-Rev Med Chem. 2017; 16: 1557–1572.
Martins P, Jesus J, Santos S, Raposo LR, Roma-Rodrigues C, Baptista PV, Fernandes AR. Heterocyclic anticancer compounds: Recent advances and the paradigm shift towards the use of nanomedicine’s tool box. MOLEFW. 2015; 20: 16852–16891. https:// doi.org/10.3390/molecules200916852
Qin SQ, Li LC, Song JR, Li HY, Li DP. Structurally simple phenanthridine analogues based on nitidine and their antitumor activities. MOLEFW. 2019; 24: 437-450. https://doi.org/10.3390/ molecules24030437
Patil V, Barragan E, Patil SA, Patil SA, Bugarin A. Direct synthesis and antimicrobial evaluation of structurally complex chalcones. Chem Select. 2016; 1: 3647–3650. https://doi.org/10.1002/slct.201600703
Vijayta G, Vinay K. A review of biological activity of imidazole and thiazole moieties and their derivatives, Sci Sci Int. 2013; 7: 253–260.
Mohammed AA. mini review: Biological significances of nitrogen heteroatom containing heterocyclic compounds. Int J Bioorg Chem. 2017; 3: 146–152.
Youness B, Younes Z, Jamal T, Ansar M. Pyridazin-3(2H)- ones: synthesis, reactivity, applications in pharmacology and agriculture. J Chem Pharm Res. 2014; 6: 297–310.
Otutu JO. Synthesis and application of azo dyes derived from 2-amino-1,3,4-thiadiazole-2-thiol on polyester fibre. Int J Res Rev Appl Sci. 2013; 15: 292–296.
Emily AB, Timothy LE. Imidazole and imidazolium-containing polymers for biology and material science applications. Polym J. 2010; 12: 2447–2454.
Anna PN, Kirtee B. Computer based drug design of various heterocyclic compounds having anticancer activity: a brief review. J Bioinformat Genom Proteom. 2017; 2: 1014-1026.
Chi-Shiang K, Chia-Chia F, Jia-Ying Y, Po-Jung T, Joseph PR, Chuan-Pin C, Yang-Hsiang C. Molecular engineering and design of semiconducting polymer dots with narrow-band, near-infrared emission for in vivo biological imaging. ACS Nano. 2017; 11: 3166–3177.
Govindarao K, Srinivasan N, Suresh R, Raheja RK, Annadurai S, Bhandare RR, Shaik AB. Quinoline conjugated 2-azetidinone derivatives as prospective anti-breast cancer agents: In vitro antiproliferative and anti-EGFR activities, molecular docking and in-silico drug likeliness studies. J Saudi Chem Soc. 2022; 26: 101471- 101489 https://doi.org/10.1016/j.jscs.2022.101471
Ji KL, Liu W, Yin WH, Li JY, Yue JM. Quinoline alkaloids with anti-inflammatory activity from Zanthoxylum avicennae. Org Biomol Chem. 2022; 20: 4176–4182. https://doi.org/10.1039/d2ob00711h
Kania A, Tejchman W, Pawlak AM, Mokrzyński K, Różanowski B, Musielak BM, Greczek-Stachura M. Preliminary studies of antimicrobial activity of new synthesized hybrids of 2-thiohydantoin and 2-quinolone derivatives activated with blue light. MOLEFW. 2022; 27: 1069-1086. https://doi.org/10.3390/molecules27031069
Prasad MVVV, Rao RHR, Veeranna V, Chennupalli VS, Sathish B. Novel quinolone derivatives: synthesis and antioxidant activity. Russ J Gen Chem. 2022; 91: 2522–2526.
Murugan K, Panneerselvam C, Subramaniam J, Paulpandi M, Rajaganesh R, Vasanthakumaran M, Madhavan J, Shafi SS, Roni M, Portilla-Pulido JS, Mendez SC, Duque JE, Wang L, Aziz AT, Chandramohan B, Dinesh D, Piramanayagam S, Hwang JS. Synthesis of new series of quinoline derivatives with insecticidal effects on larval vectors of malaria and dengue diseases. Sci Rep. 2022; 12: 4765-4775. https://doi.org/10.1038/s41598-022-08397-5
Moodley R, Mashaba C, Rakodi GH, Ncube NB, Maphoru MV, Balogun MO, Jordan A, Warner DF, Khan R, Tukulula M. New quinoline-urea-benzothiazole hybrids as promising antitubercular agents: Synthesis, in vitro antitubercular activity, cytotoxicity studies, and in silico ADME profiling. J Pharm. 2022; 15: 576-594. https://doi. org/10.3390/ph15050576
Loiseau PM, Balaraman K, Barratt G, Pomel S, Durand R, Frézard F, Figadère B. The potential of 2-substituted quinolines as antileishmanial drug candidates. MOLEFW. 2022; 27: 2313-2333. https://doi.org/10.3390/molecules27072313
Singh VK, Mishra R, Kumari P, Som A, Yadav AK, Ram NK, Kumar P, Schols D, Singh RK. In silico design, synthesis and anti-HIV activity of quinoline derivatives as non-nucleoside reverse transcriptase inhibitors (NNRTIs). Comput Biol Chem.2022; 98: 107675. https:// doi.org/10.1016/j.compbiolchem.2022.107675
Dorababu A. Quinoline: A promising scaffold in recent antiprotozoal drug discovery. Chem Select. 2021; 6: 2164–2177. https://doi. org/10.1002/slct.202100115
Krstulović L, Stolić I, Jukić M, Opačak-Bernardi T, Starčević K, Bajić M, Glavaš-Obrovac I. New quinoline-arylamidine hybrids: synthesis, DNA/RNA binding and tumor activity. Eur J Med Chem. 2017; 137: 196–210.
Bhupathi GM, Padmalatha K, Anusha A, Rameeza A, Sravanthi MG, Praneetha S. Synthesis, characterization and antimicrobial activity of acetanilide derivatives by using aromatic aldehydes and sulphonamide derivatives. Res J Pharm Technol. 2016; 9: 1846-1854. https://doi.org/10.5958/0974-360x.2016.00377.2
Upadhayaya RS, Vandavasi JK, Vasireddy NR, Sharma V, Dixit SS, Chattopadhyaya J. Design, synthesis, biological evaluation and molecular modelling studies of novel quinoline derivatives against Mycobacterium tuberculosis. Bioorg & Med Chem. 2009; 7: 2830– 2841. https://doi.org/10.1016/j.bmc.2009.02.026
Abdel M. Synthesis, Reactions and Antimicrobial Activity of 2-Amino-4-(8-Quinolinol-5-Yl)-1-(p-Tolyl)-Pyrrole-3- Carbonitrile. Bull Korean Chem Soc .2005; 26: 719–728, doi:10.5012/ bkcs.2005.26.5.719.
Ökten S, Aydın A, Koçyiğit ÜM, Çakmak O, Erkan S, Andac CA, Taslimi P, Gülçin İ. Quinoline‐based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors. Archiv Der Pharmazie. 2020; 353: 2000086. https://doi.org/10.1002/ ardp.202000086
Mathada BSD, Mathada MBH. Synthesis and Antimicrobial Activity of Some 5-Substituted-3-phenyl-N.BETA.-(Substituted- 2-oxo-2H-pyrano[2,3-b]quinoline-3-carbonyl)-1H-indole-2- carboxyhydrazide. Chem Pharm Bull. 2009; 57: 557–560. https:// doi.org/10.1248/cpb.57.557
Guruprasad BV, Mruthyunjayaswamy BHM. Synthesis and Antimicrobial Activity of Some New 3-Chloro-6-Substituted- N-(Substituted 2H-Oxazinoquinolin-3-(4H,5aH,9aH)-yl Benzo Thiophene-2-Carboxamides”. Indian J Chem. 2012; 51: 514–520.
Salman GA, Zinad DS, Mahal A, Pratama MRF, Duan M, Alkhouri A, Alamiery A. Synthesis, antibacterial activity, and molecular docking study of bispyrazole‐based derivatives as potential antibacterial agents. Chem Select. 2022; 7: 901-907. https://doi.org/10.1002/ slct.202103901
Bazine I, Bendjedid S, Boukhari A. Potential antibacterial and antifungal activities of novel sulfamidophosphonate derivatives bearing the quinoline or quinolone moiety. Archiv Der Pharmazie. 2021; 354: 291-304. https://doi.org/10.1002/ardp.202000291
Published
Abstract Display: 436 
PDF Downloads: 491 
