Design, Synthesis, And Biological Activity Of Some Novel Quinoline Derivatives
DOI:
https://doi.org/10.63682/jns.v14i7.6078Keywords:
Quinoline, Anthelminthic, Antibacterial, Albendazole, AmikacinAbstract
Here, some novel quinoline derivatives are presented in an effort to synthesise some molecules with strong antioxidant activity. First, 7-methyl or 8-methyl substituted 2-cholro-3-formylquinolines (Ia, b) were made utilising the Vilsemeir-Hack reagent method. Additional substitutions of 7-methyl or 8-methyl Compound (I) reacted with 4M HCl upon microwave irradiation to produce 2-hydroxy quinoline-3-carbaldehyde (IIa, b). Subsequent treatment with various substituted hydrazides produced the new Schiff bases of quinoline III (a-f). TLC and melting point were used to assess the synthesised compounds' purity. Using spectral analyses including infrared, 1H NMR, and mass spectroscopy, the structure of every freshly synthesised molecule was verified. Antibacterial and anthelminthic properties were investigated for each synthesised molecule. The compounds IIIb and IIIc had good effectiveness against both Gram-positive and Gram-negative bacteria, according to the data. All of the organisms were moderately active against compounds IIb and IIIf. However, when compared to the common medication amikacin, none of the compounds have demonstrated as much antibacterial efficacy. The anthelminthic activity of compounds IIIe and IIIf was moderate, while that of compounds IIIa and IIIc was good. But when compared to the common medication albendazole, none of the substances have demonstrated as much anthelmintic activity. According to the study, substances that contain quinoline derivatives with an acridine moiety have antibacterial action against Salmonella typhi, Pseudomonas aeruginosa, Bacillus subtilis, Bacillus cereus, Staphylococcus epidermidis, and Klebsiella pneumoniae. These compounds have good anthelmintic action as well. The green synthesis method mentioned above might be the best option for future industrial uses as well as medical requirements.
Downloads
Metrics
References
Wimmer RA et al. Inhibition of CBLB protects from lethal Candida albicans sepsis. Nat. Med.2016;22(8):915–23.
Pfaller MA, Diekema DJ. Epidemiology of invasive candidiasis: a persistent public health problem. Clin Microbiol Rev. 2007; 20(1): 133-63.
Rueping MJ, Vehreschild JJ, Cornely OA. Invasive candidiasis and candidemia: from current opinions to future perspectives. Expert Opin Investig Drugs 2009; 18(6):735-48.
Perlroth J, Choi B, Spellberg B. Nosocomial fungal infections: epidemiology, diagnosis, and treatment. Med Mycol. 2007;45(4):321–46.
Ammar YA, El-Sharief MA, Ghorab MM, Mohamed YA, Ragab A. New Imidazolidine iminothione. Imidazolidin-2-one and Imidazoquinoxaline Derivatives: Synthesis and Evaluation of Antibacterial and Antifungal Activities. Curr Org Synth. 2016;13(3):466–75.
Abbas SY, El-Sharief MAMS, Basyouni WM, Fakhr IMI, El-Gammal EW. Thiourea derivatives incorporating a hippuric acid moiety: synthesis and evaluation of antibacterial and antifungal activities. Eur J Med Chem 2013; 64:111–20.
Vishvakarma P. Design and development of montelukast sodium fast dissolving films for better therapeutic efficacy. Journal of the Chilean Chemical Society. 2018 Jun;63(2):3988-93.
Thomas KD, Adhikari AV, Telkar S, Chowdhury IH, Mahmood R, Pal NK et al. Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents. Eur J Med Chem 2011;46(11):5283–92.
de Souza MV, Pais M, Kaiser KC, Peralta CR. Synthesis and in vitro antitubercular activity of a series of quinoline derivatives. Bioorg Med Chem 2009;17(4):1474–80.
Prabhakar Vishvakarma, Jaspreet Kaur, Gunosindhu Chakraborthy, Dhruv Kishor Vishwakarma, Boi Basanta Kumar Reddy, Pampayya Thanthati, Shaik Aleesha, Yasmin Khatoon. Nephroprotective Potential of Terminalia Arjuna Against Cadmium-Induced Renal Toxicity by In-Vitro Study. J. Exp. Zool. India Vol. 28, No. 1, pp. 939-944, 2025.
Sun J, Lv P-C, Yin Y, Yuan R-J, Ma J, Zhu H-L. Synthesis, structure and antibacterial activity of potent DNA gyrase inhibitors: N’-benzoyl- 3-(4-bromophenyl)-1H-pyrazole-5-carbohydrazide derivatives. PLoS One 2013;8(7): e69751.
Prabhakar V, Agarwal S, Chauhan R, Sharma S. Fast dissolving tablets: an overview. International Journal of Pharmaceutical Sciences: Review and Research. 2012;16(1):17
Fayed EA, Eissa SI, Bayoumi AH, Gohar NA, Mehany ABM, Ammar YA. Design, synthesis, cytotoxicity and molecular modeling studies of some novel fluorinated pyrazole-based heterocycles as anticancer and apoptosis-inducing agents. Mol Divers. 2019; 23(1):165– 181
Mandal S, Vishvakarma P, Verma M, Alam MS, Agrawal A, Mishra A. Solanum Nigrum Linn: an analysis of the Medicinal properties of the plant. Journal of Pharmaceutical Negative Results. 2023 Jan 1:1595-600
Peytam F, Adib M, Shourgeshty R, Mohammadi-Khanaposhtani M, Jahani M, Manpreet S et al. Design and synthesis of new imidazo[1,2-b] pyrazole derivatives. in vitro α-glucosidase inhibition, kinetic and docking studies. Mol Divers. 2020;24(1):69–80.
Wang S, Liu H, Lei K, Li G, Li J, Wei Y et al. Synthesis of 3,4-dihydroquinolin-2(1H)-one derivatives with anticonvulsant activity and their binding to the GABAA receptor. Bioorg Chem 2020; 103:104182.
Vishvakarma P, Mandal S, Pandey J, Bhatt AK, Banerjee VB, Gupta JK. An Analysis Of The Most Recent Trends In Flavoring Herbal Medicines In Today's Market. Journal of Pharmaceutical Negative Results. 2022 Dec 31:9189-98
Tseng CH, Tung CW, Peng SI, Chen YL, Tzeng CC, Cheng CM. Discovery of pyrazolo[4,3-c] quinolines derivatives as potential anti- inflammatory agents through inhibiting of no production. Molecules 2019; 23(5):1–12.
Arafa RK, Hegazy GH, Piazza GA, Abadi AH. Synthesis and in vitro antiproliferative effect of novel quinoline-based potential anticancer agents. Eur J Med Chem 2013; 63:826–32.
Kumar S, Goel N, Afzal O, Ali MR, Bawa S. In-vitro antibacterial/antifungal screening of 2-chloroquinoline scaffold derivatives. J Antibiot Res 2015;1(1):101.
Asnani AJ, Sahare S. Synthesis and pharmacological studies of some novel benzoquinoline derivatives. Asian J Pharm Clin Res 2013;6 Suppl 2:303-8.
Niezen JH, Waghorn GC, Charleston WA. Growth and gastrointestinal nematode parasitism in lambs grazing either Lucerne (Medicago sativa) or (Hedysarum coronarium), which contains condensed tannins. J Agri Sci. 1995;125:281–9.
Mandal S, Vishvakarma P. Nanoemulgel: A Smarter Topical Lipidic Emulsion-based Nanocarrier. Indian J of Pharmaceutical Education and Research. 2023;57(3s):s481-98.
Athanasiadou S, Kyriazakis I, Jackson F, Coop RL. Direct anthelmintic effects of condensed tannins towards different gastrointestinal nematodes of sheep: in vitro and in vivo studies. Vet Parasitol. 2001;99:205–19. doi: 10.1016/s0304-4017(01)00467-8.
Thompson DP, Geary TG. The structure and function of helminth surfaces. In: Marr JJ, editor. Biochemistry and Molecular Biology of Parasites. 1st ed. New York: Academic Press; 1995. pp. 203–32.
Rossiter S, Péron JM, Whitfield PJ, Jones K. Synthesis and anthelmintic properties of arylquinolines with activity against drug-resistant nematodes. Bioorg Med Chem Lett 2005;15(21):4806-8.
Muruganantham N, Sivakumar R, Anbalagan N, Gunasekaran V, Leonard JT. Synthesis, anticonvulsant and antihypertensive activities of 8-substituted quinoline derivatives. Biol Pharm Bull 2004;27(10):1683-7.
Rano TA, Sieber-McMaster E, Pelton PD, Yang M, Demarest KT, Kuo GH. Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1,2,3,4-tetrahydroquinoline platform. Bioorg Med Chem Lett 2009;19(9):2456-60
Sampat VM, Mute VM, Patel KA, Sanghavi K, Mirchandani D, Babaria PC. Anthelmintic effect of Tamarindus indica Linn leaves juice extract on Pheretima posthuma. Int J Pharm Res Dev. 2009;7:1–7.
Wen X, Wang SB, Liu DC, Gong GH, Quan ZS. Synthesis and evaluation of the anti-inflammatory activity of quinoline derivatives. Med Chem Res 2015;24(6):2591.
Ramjith US, Radhika G, Muhammed Shakeel KV, Nabeel CK, Cherian A. Conventional and microwave assisted synthesis of novel quinoline derivatives and their antimicrobial and antioxidant potential. Int J Pharm Pharm Sci 2013;5 Suppl 4:521-4.
Fakhfakh MA, Fournet A, Prina E, Mouscadet JF, Franck X, Hocquemiller R, et al. Synthesis and biological evaluation of substituted quinolines: Potential treatment of protozoal and retroviral co-infections. Bioorg Med Chem 2003;11(23):5013-23.
Ghosh J, Swarup V, Saxena A, Das S, Hazra A, Paira P, et al. Therapeutic effect of a novel anilidoquinoline derivative, 2-(2-methyl-quinoline-4ylamino)-N-(2-chlorophenyl)-acetamide, in Japanese encephalitis: Correlation with in vitro neuroprotection. Int J Antimicrob Agents 2008;32(4):349-54.
Ajaiyeoba EO, Onocha PA, Olarenwaju OT. In-vitro anthelmintic properties of Buchholzia coiaceae and Gynandropsis gynandra extract. Pharm Biol. 2001;39:217–20.
Chandrashekhar CH, Latha KP, Vagdevi HM, Vaidya VP. Anthelmintic activity of the crude extracts of Ficus racemosa. Int J Green Pharm. 2008;2:100–3.
Downloads
Published
How to Cite
Issue
Section
License
This work is licensed under a Creative Commons Attribution 4.0 International License.
You are free to:
- Share — copy and redistribute the material in any medium or format
- Adapt — remix, transform, and build upon the material for any purpose, even commercially.
Terms:
- Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
- No additional restrictions — You may not apply legal terms or technological measures that legally restrict others from doing anything the license permits.
