Design and synthesis of 2-quinolones as antioxidants and antimicrobials: A rational approach

Medicinal Chemistry Research

Volumn 19, Issue 2, 2010, Pages 193-209

  Jayashree, B S ^a   Thomas, Seeja ^a   Nayak, Yogendra ^a  

^a MANIPAL COLLEGE OF PHARMACEUTICAL SCIENCES   (India)

Author keywords

2 quinolones; Antibacterial; Antioxidant; Carboxamides; Docking simulations; QSAR analysis

Indexed keywords

7 AMINO 4 METHYLQUINOLIN 2(1H) ONE; AMIDE; ANTIBIOTIC AGENT; ANTIOXIDANT; BACTERIAL DNA; DNA TOPOISOMERASE (ATP HYDROLYSING) A; N(1H) 7 (1' NAPTHOYLBENZOYLAMINO) 4 METHYLQUINOLIN 2(1H) ONE; N(1H) 7 (4' CHLOROBENZOYLAMINO) 4 METHYLQUINOLIN 2(1H) ONE; N(1H) 7 (ACETAMIDO) 4 METHYLQUINOLIN 2(1H) ONE; N(1H) 7 (BENZOYLAMINO) 4 METHYLQUINOLIN 2(1H) ONE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; COMPUTER PROGRAM; CONTROLLED STUDY; DRUG DESIGN; DRUG DETERMINATION; DRUG PURIFICATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; DRUG TARGETING; INFRARED RADIATION; MASS SPECTROMETRY; MELTING POINT; MOLECULAR DOCKING; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; THIN LAYER CHROMATOGRAPHY;

EID: 77953321223     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-009-9184-x     Document Type: Article

References (22)

1. Beckett AH, Stenlake JB (2005) Practical pharmaceutical chemistry, Part II, 4th edn. CBS Publishers and Distributors, New Delhi, India, pp 275-278
2. Boehm HJ, Boehringer M, Bur D, Gmuender H, Huber W, Klaus W, Kostrewa D, Kuehne H, Luebbers T, Meunier-Keller N, Mueller F (2000) Novel inhibitors of DNA gyrase: 3D structure based biased needle screening, hit validation by biophysical methods, and 3D guided optimization: promising alternative to random screening. J Med Chem 43:2664-2674. doi:10.1021/jm000017s
3. Chatterji M, Unniraman S, Mahadevan S, Nagaraja V (2001) Effect of different classes of inhibitors on DNA gyrase from Mycobacterium smegmatis. J Antimicrob Chemother 48:479-485. doi: 10.1093/jac/48.4.479
4. Cooper CS, Klock PL, Chu DT, Hardy DJ, Swanson RN, Plattner JJ (1992) Preparation and in vitro and in vivo evaluation of quinolines with selective activity against gram positive organisms. J Med Chem 35: 1392-1398. doi:10.1021/jm00086a007
5. Cruikshank R, Duguid JP, Marmion BP, Swain RH (1975) Medical microbiology, 2nd edn. Churchill Livingstone, NY, USA, p 190
6. Danysz W, Parsons CG (1998) Glycine and N-methyl-D-aspartate receptors: physiological significance and possible therapeutic applications. Pharmacol Rev 50:597-664
7. Dodia N, Shah A (2001) Synthesis and anti-HIV studies of some substituted pyrimidinediones, ethoxypyranon [3,2-C] quinolines and hydrazinopyrano [3,2-C] quinolines. Indian J Pharm Sci 63: 211-215
8. Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR (2004) Vogel's textbook of practical organic chemistry, 5th edn. Pearson Education, Delhi, India, p 1074
9. Heddle J, Maxwell A (2002) Quinolone-binding pocket of DNA gyrase: role of GyrB. Antimicrob Agents Chemother 46:1805-1815. doi:10.1128/AAC.46.6.1805- 1815.2002
10. Jain SC, Pandey MK, Upadhyay RK, Kumar R, Hundal G, Hundal MS (2006) Alkaloids from Toddalia aculeata. Phytochemistry 67:1005-1010. doi:10.1016/j.phytochem.2006.03.012
11. Joseph B, Darro F, Behard A, Frydman A, Lesur B, Collignon F (2002) 3-Aryl-2-quinolone derivatives: synthesis and characterization of in vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration. J Med Chem 45:2543-2555. doi:10.1021/jm010978m
12. Leclerc G, Marciniak G, Decker N, Schwartz J (1986) Cardiotonic agents. 1. Synthesis and structure-activity relationships in a new class of 3-, 4-, and 5-pyridyl-2(1H)-quinolone derivatives. J Med Chem 29:2427-2432. doi:10.1021/jm00162a002
13. Lee HZ (1997) Inhibitory effect of 2-phenyl-4-quinolone on serotonin-mediated changesin the morphology and permeability of endothelial monolayers. Eur J Pharmacol 335:245-254. doi:10.1016/S0014-2999(97)01203-X
14. Milecki J, Baker SP, Standifer KM, Ishizu T, Chida Y, Kusiak JW (1987) Carbostyril derivatives having potent β-adrenergic agonist properties. J Med Chem 30:1563-1566. doi:10.1021/jm00392a006
15. Pan XS, Fisher LM (1998) DNA gyrase and topoisomerase IV are dual targets of clinafloxacin action in streptococcus pneumonia. Antimicrob Agents Chemother 42:2810-2816
16. Raitio KH, Savinainen JR, Vepsalainen J, Laitinen JT, Poso A, Jarvinen T, Nevalainen T (2006) Synthesis and SAR studies of 2-oxoquinoline derivatives as CB2 receptor inverse agonists. J Med Chem 49:2022-2027. doi:10.1021/jm050879z
17. Rajakumar DV, Rao MN (1995) Antioxidant properties of phenyl styryl ketones. Free Radic Res 22:309-317. doi:10.3109/10715769509145643
18. Schechner M, Scirockin F, Stote RH, Dejaegere AP (2004) Functionality maps of the ATP-binding site of DNA gyrase-B: generation of a consensus model of ligand binding. J Med Chem 47:4373-4390. doi: 10.1021/jm0311184
19. Selassie CD (2003) History of quantitative structure-activity relationship: Burger's medicinal chemistry and drug discovery, vol I, 6th edn. Wiley InterScience, Hoboken, NJ, pp 15-23
20. Taylor PJ (2005) Hydrophobic properties of drug in comprehensive medicinal chemistry, vol IV, 1st edn. Elsevier, Pergamon Press, Oxford, UK, pp 270-273
21. Thomsen R, Christensen MH (2006) MolDock: a new technique for high-accuracy molecular docking. J Med Chem 49:3315-3321. doi:10.1021/jm051197e
22. Tikhonova IG, Baskin II, Palyulin VA, Zefirov NS (2003) CoMFA and homology-based models of the glycine binding site of N-methyl-D-aspartate receptor. J Med Chem 46:1609-1616. doi:10.1021/jm0210156