Design, synthesis and in vivo/in vitro screening of novel chlorokojic acid derivatives

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 28, Issue 3, 2013, Pages 627-638

  Karakaya, Gülşah ^a   Aytemir, Mutlu Dilsiz ^a   Özçelik, Berrin ^b   Çaliş, Ünsal ^a  

^a HACETTEPE UNIVERSITY   (Turkey)

^b GAZI UNIVERSITY   (Turkey)

Author keywords

Anticonvulsant; Antimicrobial; Antimycobacterial; Chlorokojic acid; Mannich bases

Indexed keywords

6 (CHLOROMETHYL) 2 {[4 (2,5 DIFLUOROBENZYL)PIPERAZIN 1 YL] METHYL} 3 HYDROXY 4H PYRAN 4 ONE; 6 (CHLOROMETHYL) 2 {[4 (CYCLOHEXANECARBONYL)PIPERAZIN 1 YL]METHYL} 3 HYDROXY 4H PYRAN 4 ONE; 6 (CHLOROMETHYL) 3 HYDROXY 2 ({4 [4 (TRIFLUOROMETHYL)BENZYL]PIPERAZIN 1 YL}METHYL) 4H PYRAN 4 ONE; 6 (CHLOROMETHYL) 3 HYDROXY 2 [(4 PHENYLPIPERAZIN 1 YL) METHYL] 4H PYRAN 4 ONE; CHLOROKOJIC ACID; KOJIC ACID; MANNICH BASE; PENTETRAZOLE; RESAZURIN; UNCLASSIFIED DRUG;

ANTICONVULSANT ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BROTH DILUTION; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; IN VIVO STUDY; MALE; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MYCOBACTERIUM AVIUM; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; OPISTHOKONTA; PRIORITY JOURNAL;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTICONVULSANTS; ANTITUBERCULAR AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MALE; MANNICH BASES; MICE; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM AVIUM; MYCOBACTERIUM TUBERCULOSIS; PENTYLENETETRAZOLE; PYRONES; SEIZURES;

FUNGI; MYCOBACTERIUM TUBERCULOSIS; NEGIBACTERIA; POSIBACTERIA;

EID: 84875398460     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2012.666538     Document Type: Article

References (49)

1. Uher M, Konecny V, Rajniakova O. Synthesis of 5-Hydroxy-2-hydroxymethyl- 4H-pyran-4-one derivatives with pesticide activity. Chem Pap 1994;48:282-284.
2. Aytemir MD, Hider RC, Erol DD, Özalp M, Ekizölu M. Synthesis of new antimicrobial agents; amide derivatives of pyranones and pyrodinones. Turkish J Chem 2003;27:445-452.
3. Aytemir MD, Erol DD, Hider RC, Özalp M. Synthesis and evaluation of antimicrobial activity of new 3-hydroxy-6-methyl-4-oxo-4Hpyran-2-carboxamide derivatives. Turkish J Chem 2003;27:757-764.
4. Aytemir MD, Calis U, Ozalp M. Synthesis and evaluation of anticonvulsant and antimicrobial activities of 3-hydroxy-6-methyl-2-substituted 4H-pyran-4-one derivatives. Arch Pharm (Weinheim) 2004;337:281-288.
5. Brtko J, Rondahl L, Ficková M, Hudecová D, Eybl V, Uher M. Kojic acid and its derivatives: History and present state of art. Cent Eur J Public Health 2004;12 Suppl:S16-S18.
6. Aytemir MD, Çal Ü. Synthesis of some new hyroxypyranone derivatives and evaluation of their anticonvulsant activities. FABAD 2006;31:23-29.
7. Aytemir MD, Çal Ü. Synthesis of some novel Mannich bases derived from allomaltol, and evaluation of their anticonvulsant activities. H U J Fac Pharm 2007;27:1-10.
8. Aytemir MD, Septioglu E, Calis U. Synthesis and anticonvulsant activity of new kojic acid derivatives. Arzneimittelforschung 2010;60:22-29.
9. Aytemir MD, Calis U. Anticonvulsant and neurotoxicity evaluation of some novel kojic acids and allomaltol derivatives. Arch Pharm (Weinheim) 2010;343:173-181.
10. Aytemir MD, Özçelik B. A study of cytotoxicity of novel chlorokojic acid derivatives with their antimicrobial and antiviral activities. Eur J Med Chem 2010;45:4089-4095.
11. Aytemir MD, Özçelik B. Synthesis and biological activities of new mannich bases of chlorokojic acid derivatives. Med Chem Res 2011;20:443-452.
12. Kasser JH, Kandioller W, Hartinger CG, Nazarov AA, Arion VB, Dyson PJ, Keppler BK. Mannich products of kojic acid and N-heterocycles and their Ru(II)Yarene complexes: Synthesis, characterization and stability. J Organomet Chem 2010;695:875-881.
13. Hryniewicz K, Stadnicka K, Adamski A, Pattek-Janczyk A. Crystal structure and the magnetic properties of tris(2-chloromethyl-4-oxo-4H-pyran-5-olato-2O5, O4)iron(III). J Coord Chem 2010;63:977.
14. Weinberg ED. The mutual effects of antimicrobial compounds and metallic cations. Bacteriol Rev 1957;21:46-68.
15. Burdock GA, Soni MG, Carabin IG. Evaluation of health aspects of kojic acid in food. Regul Toxicol Pharmacol 2001;33:80-101.
16. Wang L. Role of epicardial QT intervals in the assessment of ventricular repolarisation dispersion. Gen Physiol Biophys 2003;22:213-220.
17. Synytsya A, Blafková P, Synytsya A, ?opíková J, Sp?vá?ek J, Uher M. Conjugation of kojic acid with chitosan. Carbohydr Polym 2008;72:21-31.
18. Veverka M, Kralovicova E. Synthesis of some biologically active derivatives of 2-hydroxymethyl-5-hydroxy-4H-pyran-4-one. Collect Czech Chem Commun 1990;55:833-840.
19. Uchino K, Nagawa M, Tanasaki Y, Oda M, Fukuchi A. Kojic acid as an anti-speck agent. Agric Biol Chem 1988;52:2609-2610.
20. Alverson J. Effects of mycotoxins, kojic acid and oxalic acid, on biological fitness of Lygus hesperus (Heteroptera: Miridae). J Invertebr Pathol 2003;83:60-62.
21. Higa Y, Kawabe M, Nabae K, Toda Y, Kitamoto S, Hara T et al. Kojic acid -absence of tumor-initiating activity in rat liver, and of carcinogenic and photo-genotoxic potential in mouse skin. J Toxicol Sci 2007;32:143-159.
22. Xiong X, Pirrung MC. Modular synthesis of candidate indolebased insulin mimics by Claisen rearrangement. Org Lett 2008;10:1151-1154.
23. Alam O, Mullick P, Verma SP, Gilani SJ, Khan SA, Siddiqui N et al. Synthesis, anticonvulsant and toxicity screening of newer pyrimidine semicarbazone derivatives. Eur J Med Chem 2010;45:2467-2472.
24. Aoyagi N, Kimura R, Murata T. Studies on passiflora incarnata dry extract. I. Isolation of maltol and pharmacological action of maltol and ethyl maltol. Chem Pharm Bull 1974;22:1008-1013.
25. Kimura R, Matsui S, Ito S, Aimoto T, Murata T. Central depressant effects of maltol analogs in mice. Chem Pharm Bull 1980;28:2570-2579.
26. Ferkany JW, Andree TH, Clarke DE, Enna SJ. Neurochemical effects of kojic amine, a GABAmimetic and its interaction with benzylamine oxidase. Neuropharmacology 1981;20:1177-1182.
27. Martin GE, Bendesky RJ. Further evidence for a GABA-like action on kojic amine. Neurosci Lett 1981;27:37-40.
28. Gupta UD, Katoch VM. Animal models of tuberculosis. Tuberculosis (Edinb) 2005;85:277-293.
29. Lew JM, Kapopoulou A, Jones LM, Cole ST. TubercuListY10 years after. Tuberculosis (Edinb) 2011;91:1-7.
30. Khoshneviszadeh M, Edraki N, Javidnia K, Alborzi A, Pourabbas B, Mardaneh J et al. Synthesis and biological evaluation of some new 1,4-dihydropyridines containing different ester substitute and diethyl carbamoyl group as anti-tubercular agents. Bioorg Med Chem 2009;17:1579-1586.
31. Tateishi Y, Hirayama Y, Ozeki Y, Nishiuchi Y, Yoshimura M, Kang J et al. Virulence of Mycobacterium avium complex strains isolated from immunocompetent patients. Microb Pathog 2009;46:6-12.
32. Sano C, Tatano Y, Shimizu T, Yamabe S, Sato K, Tomioka H. Comparative in vitro and in vivo antimicrobial activities of sitafloxacin, gatifloxacin and moxifloxacin against Mycobacterium avium. Int J Antimicrob Agents 2011;37:296-301.
33. Kamal A, Shetti RV, Azeeza S, Swapna P, Khan MN, Khan IA et al. Anti-tubercular agents. Part 6: Synthesis and antimycobacterial activity of novel arylsulfonamido conjugated oxazolidinones. Eur J Med Chem 2011;46:893-900.
34. Saquib M, Husain I, Sharma S, Yadav G, Singh VK, Sharma SK et al. 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new antitubercular agents: Design, synthesis, biological evaluation and SAR studies. Eur J Med Chem 2011;46:2217-2223.
35. Nascimento GGF, Locatelli J, Freitas PC, Silva GL. Antibacterial activity of plant extracts and phytochemicals on antibiotic resistant bacteria. Braz J Microbiol 2000;31:247-256.
36. Krall RL, Penry JK, White BG, Kupferberg HJ, Swinyard EA. Antiepileptic drug development: II. Anticonvulsant drug screening. Epilepsia 1978;19:409-428.
37. CLSI (formerly NCCLS), approved stand. M27-A, 15, 10, NCCLS, VA Med. Center, Tuscon, 1996.
38. CLSI (formerly NCCLS), NCCLS document M100-S12, 940 West Valley Road, Wayne, Pennsylvania 19087, 2002.
39. Özçelik B, Orhan I, Toker G. Antiviral assessment againts Herpes simplex virus and Parainfluenza-3 virus in Vero cell line and Madin-Darby bovine kidney Cells and Antimicrobial activity of some flavonoids. Z Naturforsch 2006;61c:632-638.
40. Ozçelik B, Gürbüz I, Karaoglu T, Yesilada E. Antiviral and antimicrobial activities of three sesquiterpene lactones from Centaurea solstitialis L. ssp. solstitialis. Microbiol Res 2009;164:545-552.
41. O'Brien G, Patterson JM, Meadow Jr. Amino derivatives of kojic acid. J Org Chem 1960;25:86-89.
42. Ichimoto I, Ueda H, Tatsumi C. Studies on kojic acid and its related ?-Pyrone compounds. Part VII. The alkylation of Kojic Acid and Pyromeconic Acid through their Mannich Base. Agric Biol Chem 1965;1:94-98.
43. WOODS LL. A new derivative of kojic acid. J Am Chem Soc 1946;68:2116.
44. Uher M, Szymonska J, Korenova A, Tomasik P. Re-examination of nucleophilic substitution in chlorokojic acid. Monatsh Chem 2000;131:301-307.
45. Ashok M, Holla BS, Poojary B. Convenient one pot synthesis and antimicrobial evaluation of some new Mannich bases carrying 4-methylthiobenzyl moiety. Eur J Med Chem 2007;42:1095-1101.
46. Us D, Berk B, Gürdal E, Aytekin N, Kocagöz T, Ça?layan B, Aksan Kurnaz I, Demir Erol D. Mannich base derivatives of 3-hydroxy-6-methyl-4H-pyran-4-one with antimicrobial activity. Turkish J Chem 2010;34:447-456.
47. Us D, Gürdal E, Berk B, Öktem S, Kocagöz T, Ça?layan B, Aksan Kurnaz I, Demir Erol D. 4H-Pyran-4-one derivatives: Leading molecule for preparation of compounds with antimycobacterial potential. Turkish J Chem 2009;33:803-812.
48. Parish T, Stoker NG. Mycobacteria: Bugs and bugbears (two steps forward and one step back). Mol Biotechnol 1999;13:191-200.
49. American Thoracic Society. Diagnosis and treatment of disease caused by nontuberculous mycobacteria. This official statement of the American Thoracic Society was approved by the Board of Directors, March 1997. Medical Section of the American Lung Association. Am J Respir Crit Care Med 1997;156 (2 Pt 2): S1-25.