SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF SOME NOVEL QUINOLINE BASED IMIDAZOLES
Abstract
A simple and convenient method has been developed for the synthesis of title compounds, 1-methyl-2-phenyl-1H-imidazo[4,5-f]-quinoline and derivatives (5a-f) in reasonable yields. The commercially available 6-nitro-quinoline-5-amine (1) is used as raw material and it is reduced conveniently using SnCl2 to give the initial intermediate, quinoline-5,6-diamine (2) in good yield. Compound 2 on consecutive steps when treated on condensation followed by cyclization generated the rest of intermediates, N6-benzylidene-quinoline-5,6-diamines (3a-f) and 2-phenyl-1H-imidazo[4,5-f]-quinolines (4a-f) respectively. The chemical structures of all newly prepared compounds were elucidated using infrared, 1H NMR and mass spectral studies as well as elemental analysis. The output of this synthetic method has been provided a series of successful biologically important structures.
Keywords: Quinoline, imidazole, antimicrobial activity
DOI
https://doi.org/10.22270/jddt.v6i5.1278References
Barnard EA, Stein WD, Adv. Enzym., 1958; 20:51.
Boiani M, Gomzalez M, Med. Chem., 2005, 5:409.
Lagoja IM, Pannecouque C, Van Aerschot A, Witvrouw M, Debyser Z, Balzarini J, Herdewijn P, De Clercq E, J. Med. Chem., 2003; 46:1546.
Nieto I, Cervantes-Lee F, Smith JM, Chem. Commun., 2005, 3811.
Herrmann WA, Angew. Chem. Int. Ed., 2002; 41:1290.
Cesar V, Bellemin-Laponnaz S, Gade LH, Chem. Soc. Rev., 2004; 33:619.
Brogden RN, Heel RC, Speight TM, Avery GS, Drugs, 1978; 16:387.
Santo RD, Tafi A, Costi R, Botta M, Artico M, Corelli F, Forte M, Caporuscio F, Angiolella L, Palamara AT, J. Med. Chem., 2005; 48:5140.
Brimblecombe RW, Duncan WAM, Durant GJ, Emmett JC, Ganellin CR, Parsons ME, J. Int. Med. Res., 1975; 3: 86.
Kanyiva KS, Lobermann F, Nakao Y, Hiyama T, Tetrahedron Lett., 2009; 50:3463.
Ramesh RD, Manian RS, Raghunathan R, Sainath S, Raghunathan M, Bioorg. Med. Chem., 2009; 17: 660.
Kaur K, Jain M, Kaur T, Jain R, Bioorg. Med. Chem., 2009; 17: 3229.
Behforouz M, Cai W, Mohammadi F, Stocksdale MG, Gu Z, Ahmadian M, Baty DE, Etling MR, Al-Anzi CH, Swiftney TM, Tanzer LR, Merriman RL, Behforouz NC, Bioorg. Med. Chem., 2007; 15:495.
Abas F, Lajis NH, Israf DA, Khozirah S, Umi Kalsom Y, Food Chemistry, 2006; 95:566.
Rocha LG, Almeida JRGS, Macedo RO, Barbosa-Filho JM, Phytomedicine, 2005; 12:514.
Reen-Yen K, Fang-Rong C, Chung-Yi C, Che-Ming T, Hsin-Fu Y, Yang Chang W, Phytochemistry, 2001; 57:421.
Jain SR, Kar A, Planta. Med., 1971; 20:118.
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