Synthesis, characterization, antimicrobial activity and structure–activity relationships of new aryldisulfonamides

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 24, Issue 4, 2009, Pages 986-992

  Alyar, Saliha ^a   Karacan, Nurcan ^a  

^a GAZI UNIVERSITY   (Turkey)

Author keywords

Antimicrobial activity; structure activity relationship; sulfonamides

Indexed keywords

ANTIINFECTIVE AGENT; SULFONAMIDE;

ANIMAL; ARTICLE; BACTERIUM; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECT; MICROBIOLOGICAL EXAMINATION; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; ANTI-BACTERIAL AGENTS; BACTERIA; CELL LINE, TUMOR; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 72649104048     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360802561220     Document Type: Article

References (43)

1. Anand, N. In Burger’s Medicinal Chemistry and Drug Discovery; Wolff, M E., Ed., 5th ed.; Therapeutic Agents; J. Wiley & Sons: New York, 1996; Vol. 2, pp 527 – 544.
2. Mastrolorenzo A, Scozzafava A, and Supuran C T. Antifungal activity of silver and zinc complexes of sulfadrug derivatives incorporating arylsulfonylureido moieties. Eur. J Pharm Sci 2000; 11 (2): 99 – 107.
3. Onisha G P, Eddy K M, Alexis M N, and Ian G M. Sulfa drugs strike more than once. Trends Parasitol 2004; 20 (1): 1 – 3.
4. Kamel A M, Lobna M.A.-A., El-Sayed M L, Mohamed I H, and Rania H B. Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents. Bioorg Med Chem. 2006; 14: 8675 – 8682.
5. Hadj-esfandiari N, Navidpour L, Shadnia H, Amini M, Samadi N, Faramarzi M A, and Shafiee A. Synthesis, antibacterial activity, and quantitative structure-activity relationships of new (Z)-2-(nitroimidazolylmethylene)-3(2H)-benzofuranone derivatives. Bioorg Med Chem Lett. 2007; 17: 6354 – 6363.
6. Khan M W, Alam M J, Rashid M A, Chowdhury R. A new structural alternative in benzo[b]furans for antimicrobial activity. Bioorg Med Chem. 2005; 13 (16): 4796 – 4805.
7. Zanatta N A, Coelho S H, Borchhardt H S, Machado D M, Flores P, Silva K M, Spader F M, Santurio T B, Bonacorso J M, Helio G, Martins M.A.P. Synthesis, antimicrobial activity, and QSAR studies of furan-3-carboxamides. Bioorg Med Chem. 2007; 15 (5): 1947 – 1958.
8. Greenfield R A, and Bronze M S. Prevention and treatment of bacterial diseases caused by bacterial bioterrorism threat agents. Drug Discov. 2003; 8 (19): 881 – 888.
9. Ezabadi I R, Camoutsis C, Zoumpoulakis P, Geronikaki A, Sokovic M, Glamocilija J, and Ciric A. Sulfonamide-1,2,4-triazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies. Bioorg Med Chem. 2008; 16 (3): 1150 – 1161.
10. Patel P R, Ramalingan C, and Park Y-T. Synthesis and antimicrobial evaluation of guanylsulfonamides. Bioorg Med Chem Lett. 2007; 17 (23): 6610 – 6614.
11. Isik, K.; Kocak F. O., Microbiol. Res., Available online 27 February 2007.
12. Fathalla O A, Zaghary W A, Radwan H H, Awad S M, and Mohamed M S. Synthesis of new 2-thiouracil-5-sulfonamide derivatives with biological activity. Arch Pharm Res. 2002; 3 (25): 258 – 269.
13. Mastrolorenzo A, Scozzafava A, Supuran C T. Antifungal activity of silver and zinc complexes of sulfadrug derivatives incorporating arylsulfonylureido moieties. Eur J Pharm Sci. 2000; 11 (2): 99 – 107.
14. Ozbek N, Katırcıoglu H, Karacan N, and Baykal T. Synthesis, characterization and antimicrobial activity of new aliphatic sulfonamide. Bioorg Med Chem. 2007; 15 (15): 5105 – 5109.
15. Alyar S, Ozbek N, Karacan N. Synthesis and antimicrobial activity of new substituted arylsulfonamides. Drug Future. 2007; 32: 126 – 127 Suppl. A
16. Ozbek N, Alyar S, Karacan N. Synthesis, characterization and antimicrobial activity of new butanesulfonamides. Drug Future 2007; 32: 128 Suppl. A
17. Ienco, A, Mealli C, Paoli P. Dodoff N I, Kantarci Z, Karacan N. Structure and vibrational spectrpscopy of methanesulfonic acid hydrazide: an experimental and theoretical study New J Chem. 1999; 23: 1253 – 1260.
18. Dodoff N I, Ozdemir U, Karacan N, Georgieva M Ch, Konstantinov S M, and Stefanova M E. Schiff Bases of Methanesulfonylhydrazine. Synthesis, Spectroscopic Characterization, Conformational Analysis and Biological Activity. Z Naturforsch. 1999; 54b: 1553 – 1562.
19. Alyar S, Ozmen U O, Karacan N, Sentürk O S, and Udachin K.A. Tautomeric properties, conformations and structure of 2-hydroxyacetophenone methanesulfonylhydrazone. J Mol Struct., Available online 12 February 2008
20. Ozdemir U, Sentürk O S, Sert S, Karacan N, Ugur F. Photochemical reactions of metal carbonyls [M(CO)(6) (M=Cr, Mo and W), Re(CO)(5)Br, Mn(CO)(3)Cp] with 2-hydroxyacetophenone methanesulfonylhydrazone (apmsh) Trans Met Chem. 2003; 28 (4): 443 – 446.
21. Sert S, Sentürk O S, Ozdemir U, Karacan N, U_ur F. Synthesis and characterization of the products from reaction of metal carbonyls [M(CO)(6) (M = Cr, Mo, W), Re(CO)(5)Br, Mn(CO)(3)Cp] with salicylaldehyde methanesulfonylhydrazone J Coord Chem. 2004; 57 (3): 183 – 188.
22. Ozdemir U, Karacan N, Sentürk O S, Sert S, U_ur F. Synthesis and characterization of metal carbonyl complexes of M(CO)(6)(M = Cr, Mo, and W), Re(CO)(5)Br, and Mn(CO)(3)CP with - Acetonemethanesulfonylhydrazone (amsh) and methanesulfonylhydrazone (msh). Synth React Inorg Met Org Chem. 2004; 34 (6): 1057 – 1067.
23. Ozdemir U, Sentürk O S, Sert S, Karacan N, U_ur F. Reaction of metal carbonyls with 2-hydroxy-1-naphthaldeyde methanesulfonylhydrazone and characterization of the substitution products. J Coord Chem. 2006; 59 (17): 1905 – 1911.
24. Ozmen U O, Olgun G. Synthesis, characterization and antibacterial activity of new sulfonyl hydrazone derivatives and their nickel(II) complexes Spectrochim Acta Part A 2008; 70 (3): 641 – 645.
25. Senturk O S, Ozdemir U, Sert S, Karacan N, U_ur F. Photochemical reactions of metal carbonyls [M(CO)(6) (M = Cr, Mo, W), Re(CO)(5)Br, Mn(CO)(3)Cp] with salicylaldehyde ethanesulfonylhydrazone (Hsalesh). J Coord Chem. 2007; 60 (2): 229 – 232.
26. Senturk O S, Ozdemir U, Sert S, Karacan N, U_ur F. Synthesis and characterization of some metal carbonyls with 2-hydroxyacetophenone ethanesulfonylhydrazone. Inorg Chem Commun. 2003; 6 (7): 926 – 929.
27. Rastenyte, L.; Jokubaityte, S.; Mozolis, V., Lietuvos TSR Mokslu Akademijos Darbai, Serija B: Chemija, Technika, Fizine Geografija, 1974, 1, 69.
28. Gajadhar-Plummer A S, Kahwa A, Mague J T. N,N0-Ethylenebis(p-toluenesulfonamide). Acta Crystallogr. Section E: 2001; E57 (1): 68 – 69.
29. Grigoryan L A, Kaldrikyan M R, Arsenyan E G, Stepanyan G M, and Garibdzhanyan B T. Arylsulfonic acid derivatives. Synthesis and antitumor activity of di- and tetra(benzylsulfonyl)diamines. Pharm Chem J. 2000; 4 (34): 186 – 188.
30. Friedman L, Litle R L, and Reichle W R., p-toluensulfonylhydrazide. Org Syntheses. 1960; 40: 93.
31. Tremayne M, Lightfoot P, Glidewell C, Harris K D M, Shankland K Gilmore C J Bricogne G, Bruce P.G. Materials chemistry communications. Application of the combined maximum entropy and likelihood method to the ab initio determination of an organic crystal structure from X-ray powder diffraction data. J Mater Chem. 1992; 2 (12): 1301 – 1302.
32. Grande F, Aiello F, Grazia O D, Brizzi A, Garofalo A, Neamati N. Synthesis and antitumor activities of a series of novel quinoxalinhydrazides. Bioorg Med Chem 2007; 15 (1): 288 – 294.
33. Yakaiah T, Lingaiah B P V, Narsaiah B, Shireesha B, Ashok Kumar B, Gururaj S, Parthasarathy T, Sridhar B. Synthesis and structure-activity relationships of novel pyrimido[1,2-b]indazoles as potential anticancer agents against A-549 cell lines. Bioorg Med Chem Lett. 2007; 17 (12): 3445 – 3453.
34. Kamal A, Khan M N A, Reddy K S, Rohini K. Synthesis of a new class of 2-anilino substituted nicotinyl arylsulfonylhydrazides as potential anticancer and antibacterial agents. Bioorg Med Chem. 2007; 15 (2), 1004 – 1013.
35. Leo A J. Calculating log Poct from structures. Chem Rev. 1993; 93: 1281 – 1306.
36. ALOGPS 2.1 software available at http://www.vcclab.org/lab/alogps.
37. Remko M, and Lieth C W. Theoretical study of gas-phase acidity, pKa, lipophilicity, and solubility of some biologically active sulfonamides. Bioorg Med Chem. 2004; 12 (20): 5395 – 5403.
38. Bell P H, and Roblin R O. Studies in Chemotherapy. VII. A Theory of the Relation of Structure to Activity of Sulfonilamide Type compounds. J Am Chem Soc. 1942; 64: 2905 – 2017.
39. HyperChem 7.5 program, Hypercube Inc Toronto, Canada, 2002.
40. http://www.talete.mi.it/ dragon_exp.htm, Italia
41. Lipinski C A, Lombardo F, Dominy B W, and Feeney P J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliver Rev. 1997; 23 (1-3): 3 – 25.
42. Wayne P A. National Committee for Clinical Laboratory Standards. Approved Standard M7-A4. 1997 and M27. 1997.
43. Bauer A W, Kirby W M, Sherries J C, Truck M. Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol. 1966; 45 (4): 493 – 496.