Synthesis, antimicrobial activity and molecular modeling study of substituted 5-aryl-pyrimido[5,4-c]quinoline-2,4-diones

References

• Brown DJ. The Pyrimidines. Interscience, New York, NY. 1994.
   Google Scholar
• Macllwain C. Activists now urge caution on approval of new AIDS drug. Nature 1993;365:378.
   PubMedGoogle Scholar
• Wamberg M, Pedersen EB, El-Brollosy NR, Nielsen C. Synthesis of 6-arylvinyl analogues of the HIV drugs SJ-3366 and Emivirine. Bioorg Med Chem 2004;12:1141–1149.
   PubMed Web of Science ®Google Scholar
• Jones AS, Sayers JR, Walker RT, De Clercq E. Synthesis and antiviral properties of (E)-5-(2-bromovinyl)-2′-deoxycytidine-related compounds. J Med Chem 1988;31:268–271.
   PubMed Web of Science ®Google Scholar
• De Clercq E. Potential of bromovinyldeoxyuridine in anticancer chemotherapy. Anticancer Res 1986;6:549–556.
   PubMed Web of Science ®Google Scholar
• Miyasaka T, Tanaka H, Baba M, Hayakawa H, Walker RT, Balzarini J et al. A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J Med Chem 1989;32:2507–2509.
   PubMed Web of Science ®Google Scholar
• Zoorob HH, Abou Elzahab M, Abdel-Mogib M, Ismail MA, Abdel-Hamid M. 1,3-Dimethylpyrimidoheterocycles as antibacterial agents. Arzneimittelforschung 1997;47:958–962.
   PubMedGoogle Scholar
• Foley M, Tilley L. Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents. Pharmacol Ther 1998;79:55–87.
   PubMed Web of Science ®Google Scholar
• Savarino A, Gennero L, Chen HC, Serrano D, Malavasi F, Boelaert JR et al. Anti-HIV effects of chloroquine: mechanisms of inhibition and spectrum of activity. AIDS 2001;15:2221–2229.
   PubMed Web of Science ®Google Scholar
• Mittmann NN, Jivarj FF, Wong AA and Yoon AA. Oral fluoroquinolones in the treatment of pneumonia, bronchitis and sinusitis. Can J Infect Dis 2002;5:293–300.
   Google Scholar
• Childs SJ. Safety of the Fluoroquinolone antibiotics: focus on molecular structure. Infect Urol 2000;13:3–10.
   Google Scholar
• Menzel R, Gellert M. The biochemistry and biology of DNA gyrase. Adv Pharmacol 1994;29A:201–225.
   PubMedGoogle Scholar
• Maxwell A, Gellert M. Mechanistic aspects of DNA topoisomerases. Adv Protein Chem 1986;38:69–107.
   PubMedGoogle Scholar
• Kampranis SC, Bates AD, Maxwell A. A model for the mechanism of strand passage by DNA gyrase. Proc Natl Acad Sci USA 1999;96:8414–8419.
   PubMedGoogle Scholar
• Brino L, Urzhumtsev A, Mousli M, Bronner C, Mitschler A, Oudet P et al. Dimerization of Escherichia coli DNA-gyrase B provides a structural mechanism for activating the ATPase catalytic center. J Biol Chem 2000;275:9468–9475.
   PubMed Web of Science ®Google Scholar
• Flatman RH, Eustaquio A, Li SM, Heide L, Maxwell A. Structure-activity relationships of aminocoumarin-type gyrase and topoisomerase IV inhibitors obtained by combinatorial biosynthesis. Antimicrob Agents Chemother 2006;50:1136–1142.
   PubMedGoogle Scholar
• Kontoyianni M, McClellan LM, Sokol GS. Evaluation of docking performance: comparative data on docking algorithms. J Med Chem 2004;47:558–565.
   PubMed Web of Science ®Google Scholar
• Wang R, Lu Y, Wang S. Comparative evaluation of 11 scoring functions for molecular docking. J Med Chem 2003;46:2287–2303.
   PubMed Web of Science ®Google Scholar
• Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 1990; 82:1107–1112.
   PubMed Web of Science ®Google Scholar
• McCaffrey TA, Agarwal LA, Weksler BB. A rapid fluorometric DNA assay for the measurement of cell density and proliferation in vitro. In Vitro Cell Dev Biol 1988;24:247–252.
   PubMed Web of Science ®Google Scholar
• Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D et al. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 1991;83:757–766.
   PubMed Web of Science ®Google Scholar
• Bauer AW, Kirby WM, Sherris JC, Turck M. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 1966;45:493–496.
   PubMed Web of Science ®Google Scholar
• Pfaller MA, Burmeister L, Bartlett MS, Rinaldi MG. Multicenter evaluation of four methods of yeast inoculum preparation. J Clin Microbiol 1988;26:1437–1441.
   PubMed Web of Science ®Google Scholar
• National Committee for Clinical Laboratory Standards. 1993. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A3. National Committee for Clinical Laboratory Standards, Villanova, PA.
   Google Scholar
• National Committee for Clinical Laboratory Standards. 1993. Performance VOL. 41, 1997 antimicrobial susceptibility of Flavobacteria
   Google Scholar
• Ali HI, Ashida N, Nagamatsu T. Antitumor studies. Part 4: Design, synthesis, antitumor activity, and molecular docking study of novel 2-substituted 2-deoxoflavin-5-oxides, 2-deoxoalloxazine-5-oxides, and their 5-deaza analogs. Bioorg Med Chem 2008;16:922–940.
   PubMed Web of Science ®Google Scholar
• Abdel-Aziz AA, ElTahir KE, Asiri YA. Synthesis, anti-inflammatory activity and COX-1/COX-2 inhibition of novel substituted cyclic imides. Part 1: Molecular docking study. Eur J Med Chem 2011;46:1648–1655.
   PubMed Web of Science ®Google Scholar
• Naya S, Miyagawa M, Nitta M. Novel photo-induced oxidative cyclization of 1,3-dimethyl-5-(1-arylmethylidene)pyrimidine-2,4,6(1,3,5H)-triones: Synthesis and properties of areno[5,6]pyrano[2,3-d]pyrimidine-2,4(1,3 H)-dionylium ions and their photo-induced autorecycling oxidizing reaction toward some amines. Tetrahedron 2005;61:4919–4930.
   Google Scholar
• Shi D, Shi J, Rong S. A facile and clean synthesis of pyrimidine derivatives via three-component reaction in aqueous media. Chin J Chem 2010;28:791–796.
   Google Scholar
• Shul’ts EE, Andreev GN, Shakirov MM, Komarova NI, Bagryanskaya IY, Gatilov YV, Tolstikov GA. Diels-Alder reactions with cyclic sulfones: VIII. Organic catalysis in the synthesis of spiro[1-benzothiophene-4,5′-pyrimidine]-2′,4′,6′-trione 1,1-dioxides and 2′-thioxo-spiro[1-benzothiophene-4,5′-pyrimidine]-4′,6′-dione 1,1-dioxides. Russian Journal of Organic Chemistry 2009; 45:87–101.
   Google Scholar
• Krasnov KA, Kartsev VG, Gorovoi AS. Chemical modification of plant alkaloids. I. Aminomethylation of barbituric acid derivatives by cytisine. Chemistry of Natural Compounds 2000;36: 192–197.
   Google Scholar
• Zoorob HH, Abou-Elzahab M, Abdel-Mogib M, Ismail MA. Peculiar reaction behaviour of barbituric acid derivatives towards aromatic amines. Tetrahedron 1996; 52(30):10147–10158.
   Google Scholar
• Mishra R, Tomar I. Pyrimidine: The Molecule of diverse biological and medicinal importance. International Journal of Pharmaceutical Sciences and Research 2011;2:758–771.
   Google Scholar
• Cheng CC, Roth B. Recent Progress in the Medicinal Chemistry of 2,4-Diaminopyrimidines. Prog Med Chem 1982;19:269–331.
   PubMedGoogle Scholar
• Kompis I, Wick A. The Synthesis of 4-Halogen-substituted Analogs of Trimethoprim. Helv Chim Acta 1977;60:3025–3034.
   Google Scholar
• Bazgir A, Khanaposhtani MM, Soorki AA. One-pot synthesis and antibacterial activities of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-dione derivatives. Bioorg Med Chem Lett 2008;18: 5800–5803.
   PubMed Web of Science ®Google Scholar
• Nelson JM, Chiller TM, Powers JH, Angulo FJ. Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: a public health success story. Clin Infect Dis 2007;44:977–980.
   PubMed Web of Science ®Google Scholar
• Ivanov DV. [Antibiotic susceptibility and molecular mechanisms of cephalosporins resistance in Klebsiella isolates from patients with hospital-acquired infections]. Antibiot Khimioter 2006;51:29–36.
   Google Scholar
• Schaumann R., Rodloff AC. Activities of quinolones against obligately anaerobic bacteria. Anti-Infective Agents in Medicinal Chemistry 2007;6:49–56.
   Google Scholar
• Holla BS, Mahalinga M, Karthikeyan MS, Akberali PM, Shetty NS. Synthesis of some novel pyrazolo[3,4-d]pyrimidine derivatives as potential antimicrobial agents. Bioorg Med Chem 2006;14:2040–2047.
   PubMed Web of Science ®Google Scholar
• Ramesh E, Manian RD, Raghunathan R, Sainath S, Raghunathan M. Synthesis and antibacterial property of quinolines with potent DNA gyrase activity. Bioorg Med Chem 2009;17:660–666.
   PubMed Web of Science ®Google Scholar
• Lafitte D, Lamour V, Tsvetkov PO, Makarov AA, Klich M, Deprez P et al. DNA gyrase interaction with coumarin-based inhibitors: the role of the hydroxybenzoate isopentenyl moiety and the 5′-methyl group of the noviose. Biochemistry 2002;41:7217–7223.
   PubMed Web of Science ®Google Scholar