Antibacterial, antifungal and cytotoxic properties of novel N-substituted sulfonamides from 4-hydroxycoumarin

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 21, Issue 6, 2006, Pages 741-748

  Chohan, Zahid H ^a   Shaikh, Ali U ^b   Rauf, Abdul ^c   Supuran, Claudiu T ^d  

^a BAHAUDDIN ZAKARIYA UNIVERSITY   (Pakistan)

^b University of Arkansas   (United States)

^c THE ISLAMIA UNIVERSITY OF BAHAWALPUR   (Pakistan)

^d UNIVERSITY OF FLORENCE   (Italy)

Author keywords

4 Hydroxycoumarin; Antibacterial; Antifungal; Cytotoxicity; Sulfonamides

Indexed keywords

3 [[4 [[[AMINO (IMINO)METHYL]AMINO]SULFONYL]ANILINO]METHYLIDENE] 2,4 DIOXO 2H CHROMENE; 4 [2 [[(2,4 DIOXO 2H CHROMEN 3(4H) YLIDENE)METHYL]AMINO]ETHYL]BENZENESULFONAMIDE; 4 [[(2,4 DIOXO 2H CHROMEN 3(4H) YLIDEN)METHYL]AMINO] N (5 METHYL 3 ISOXAZOLYL)BENZENESULFONAMIDE; 4 [[(2,4 DIOXO 2H CHROMEN 3(4H) YLIDENE)METHYL]AMINO] N (1,3 THIZOL 2 YL)BENZENESULFONAMIDE; 4 [[2 [[(2,4 DIOXO 2H CHROMEN 3(4H) YLIDENE)METHYL]AMINO] 4 PYRIMIDINYL]AMINO]BENZENESULFONAMIDE; 4 [[[(2,4 DIOXO 2H CHROMEN 3(4H) YLIDINE)METHYL]AMINO]METHYL]BENZENESULFONAMIDE; 4 HYDROXYCOUMARIN DERIVATIVE; 4[[[2,4 DIOXO 2H CHROMEN 3(4H) YLIDENE]METHYL]AMINO]BENZENESULFONAMIDE; AMPHOTERICIN B; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; IMIPENEM; MICONAZOLE; N (4,6 DIMETHYL 2 PYRIMIDINYL) 4 [[(2,4 DIOXO 2H CHROMEN 3(4H) YLIDENE)METHYL]AMINO]BENZENESULFONAMIDE; SULFONAMIDE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC SENSITIVITY; ANTIFUNGAL ACTIVITY; ARTEMIA; ARTEMIA SALINA; ARTICLE; ASPERGILLUS FLAVUS; BACILLUS SUBTILIS; BACTERIAL STRAIN; BIOASSAY; CANDIDA ALBICANS; CANDIDA GLABRATA; CONCENTRATION RESPONSE; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; FUNGAL STRAIN; FUSARIUM SOLANI; IN VITRO STUDY; LD 50; MICROSPORUM CANIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHI; SHIGELLA FLEXNERI; STAPHYLOCOCCUS AUREUS; STRAIN DIFFERENCE; TRICHOPHYTON; TRICHOPHYTON LONGIFUSUS;

4-HYDROXYCOUMARINS; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CYTOTOXINS; ENZYME INHIBITORS; MICROBIAL SENSITIVITY TESTS; SULFONAMIDES;

ANOSTRACA; ARTEMIA SALINA; BACTERIA (MICROORGANISMS); NEGIBACTERIA; POSIBACTERIA; SALMONELLA TYPHI; STAPHYLOCOCCUS AUREUS;

EID: 33845734145     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360600810340     Document Type: Article

References (32)

1. Supuran, CT and Nicolae, A and Popescu, A. (1996) Carbonic anhydrase inhibitors Eur J Med Chem, 31, pp. 43-48. Part 35. Synthesis of Schiff bases derived from sulfanilamide and aromatic aldehydes: The first inhibitors with equally high affinity towards cytosolic and membrane-bound isoenzymes
2. Supuran, CT and Popescu, A and Ilisiu, M and Costandache, A and Banciu, MD. (1996) Carbonic anhydrase inhibitors Eur J Med Chem, 31, pp. 439-447. Part 36. Inhibition of isoenzymes I and II with Schiff bases derived from chalkones and aromatic/heterocyclic sulfonamides
3. Supuran, CT and Scozzafava, A and Popescu, A and Bobes-Tureac, R and Banciu, A and Creanga, A and Bobes-Tureac, G and Banciu, MD. (1997) Carbonic anhydrase inhibitors Eur J Med Chem, 32, pp. 445-452. Part 43. Schiff base derived from aromatic sulfonamides: Towards more specific inhibitors for membrane-bound versus cytosolic isoenzymes
4. Popescu, A and Simion, A and Scozzafava, A and Briganti, F and Supuran, CT. (1999) Carbonic anhydrase inhibitors J Enz Inhib, 14, pp. 407-423. part 67 Schiff bases of some aromatic sulfonamide and their metal complexes: Towards more selective inhibitors of carbonic anhydrase isozyme IV.
5. Scozzafava, A and Banciu, MD and Popescu, A and Supuran, CT. (2000) Carbonic anhydrase inhibitors: Part 90 J Enz Inhib, 15, pp. 533-540. Synthesis of Schiff basees of hydroxybenzaldehyde with aromatic sulfonamides and their reactions with sulfonyl isocyanates
6. Hassan, M and Scozzafava, A and Chohan, ZH and Supuran, CT. (2001) Carbonic anhydrase inhibitors: Metal complexes of a sulfonamide derived Schiff base and their interaction with isozymes I, II and IV J Enz Inhib, 16, pp. 499-505.
7. Hassan, M and Chohan, ZH and Scozzafava, A and Supuran, CT. (2004) Carbonic anhydrase inhibitors: Schiff's bases of aromatic and heterocyclic sulfonamides and their metal complexes J Enz Inhib Med Chem, 19, pp. 263-267.
8. Winum, JY and Casini, A and Mincione, F and Starnotti, M and Montero, JL and Scozzafava, A and Supuran, CT. (2004) Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-α-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits Bioorg Med Chem Lett, 14, pp. 225-229.
9. Vullo, D and Innocenti, A and Nishimori, I and Pastorek, J and Scozzafava, A and Pastorekova, S and Supuran, CT. (2005) Carbonic anhydrase inhibitors Bioorg Med Chem Lett, 15, pp. 963-969. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs
10. Hoult, JRS and Payd, M. (1996) Pharmacological and biochemical actions of simple coumarins: Natural products with theraeutic potential Gen Pharmacol 27, pp. 713-722.
11. Hossain, CF and Okoyama, E and Yamazaki, M. (1996) A new series of coumarin derivatives having monoamine oxidase inhibitory activity Chem Pharm Bull, 44, pp. 1535-1539.
12. Oliva, A and Meepagala, KM and Wedge, DE and Harries, D and Hale Al and Aliotta, G and Duke, SO. (2003) Natural fungicides from Ruta graveolens L. leaves, including a new quinolon alkaloid J Agric Fd Chem, 51, pp. 890-896.
13. Manolov, L and Danchev, ND. (1995) Synthesis, toxicological and pharmacological assessment of some 4-hydroxycoumarin derivatives Eur J Med Chem, 30, pp. 531-535.
14. Romines, KR and Morris, JK and Howe, WJ and Tomich, RK and Hong, M-M and Chong, K-T and Hinshaw, RR and Anderson, DJ and Strohbach, JW and Turner, SR and Mizsak, SA. (1996) Cycloalkylpyranones and Cycloalkyldihydropyrones as HIV Protease Inhibitors: Exploring the Impact of Ring Size on Structure-Activity Relationships J Med Chem, 39, pp. 4125-4130.
15. Zhao, H and Neamah, N and Hong, H and Majumber, A and Wang, S and Sunder, S and Milne, GWA and Pommier, Y and Bruke, TR. (1997) Coumarin-Based Inhibitors of HIV Integrase J Med Chem, 40, pp. 242-249.
16. Thaisrivongs, S and Romero, DL and Tommasi, RA and Janakiraman, MN and Strohbach, JW and Turner, SR and Biles, C and Morge, RR and Johnson, PD and Aristoff, PA and Tomich, PK and Lynn, JC and Horng, MM and Chong, KT and Hinshaw, RR and Howe, WJ and Finzel, BC and Watennpaugh, KD. (1996) Structure-Based design of HIV protease inhibitors: 5,6-Dihydro-4-hydroxy-2-pyrones as effective, nonpeptidic inhibitors J Med Chem, 39, pp. 4630-4642.
17. Chohan, ZH and Hassan, MU and Khan, KM and Supuran, CT. (2005) In-vitro antibacterial, antifungal and cytotoxic properties of sulfonamide-derived schiff's bases and their metal complexes J Enz Inhib Med Chem, 20, pp. 183.
18. Ferroud, D and Collard, J and Klich, M and Dupuis-Hamelin, C and Mauvais, P and Lassaigne, P and Bonnefoy, A and Musicki, B. (1999) Synthesis and biological evaluation of coumarincarboxylic acids as inhibitors of gyrase B, L-Rhamnose as an effective substitute for L-Noviose Bioorg Med Chem Lett, 9, pp. 2881-2886.
19. Han, S and Zhou, V and Pan, S and Liu, Y and Hornsby, M and McMullan, D and Klock, HE and Haugen, J and Lesley, SA and Nathanael, G and Calwell, J and Gu, X-J. (2005) Identification of Coumarin Derivatives as a Novel Class of Allosteric MEKI Inhibitors Bioorg Med Chem Lett, 15, pp. 5467-5473.
20. Chen, S and Cho, M and Karlsberg, K and Zhou, D and Yuan, Y-C. (2004) Biochemical and biological characterization of a novel anti-aromatase coumarin derivative J Biolog Chem, 12, pp. 48071-48078.
21. Bandyopadhyay, C and Sur, KR and Patra, R and Sen, A. (2000) Synthesis of coumarin derivatives from 4-oxo-4H-1-benzopyran-3-carboxaldehyde via 3-(arylaminomethylene)chroman-2,4-dione Tetrahedron, 56, pp. 3583-3587.
22. Takechi, H and Oda, Y and Nishizono, N and Oda, K and Machida, M. (2000) Screening search for organic fluorophores: Synthesis and fluorescence properties of 3-azolyl-7-diethylaminocoumarin derivatives Chem Pharm Bull, 48, pp. 1702-1710.
23. Atta-ur-Rahman and Choudhary, MI and Thomsen, WJ.(2001) Bioassay Techniques for Drug Development. The Netherlands: Harwood Academic Publishers.
24. McLaughlin, JL and Chang, C-J and Smith, DL.(1991) Studies in Natural Products Chemistry, 'Bentch-Top' Bioassays for the Discovery of Bioactive Natural Products: An update, Structure and Chemistry (part-B). The Netherlands: Elsevier Science Publishers B.V.
25. Meyer, BN and Ferrigni, NR and Putnam, JE and Jacobsen, LB and Nichols, DE and McLaughlin, JL. (1982) Planta Medica 45, pp. 31.
26. Finney, DJ.(1971) Probit Analysis 3rd ed. Cambridge: Cambridge University Press.
27. Hamdi, M and Sakellariou, R and Speziale, V. (1992) J Heterocyclic Chem, 29, pp. 1817.
28. Nakamoto, K.(1970) Infrared Spectra of Inorganic and Coordination Compounds 2nd ed. New York: Wiley Interscience.
29. Bellamy, LJ.(1971) The Infrared Spectra of Complex Molecules. New York: John Wiley.
30. Simmons, WW.(1978) The Sadtler Handbook of Proton NMR Spectra. Inc: Sadtler Research Laboratories.
31. Pasto, DJ.(1969) Organic Structure Determination. London: Prentice Hall International.
32. Bauer, AW and Kirby, WM and Sherris, JC and Turck, M and Am, J. (1966) Clin Pathol, 45, pp. 493.