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

References

• 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.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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 AP. Synthesis, antimicrobial activity, and QSAR studies of furan-3-carboxamides. Bioorg Med Chem. 2007;15(5):1947–1958.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Patel P R, Ramalingan C, and Park Y-T. Synthesis and antimicrobial evaluation of guanylsulfonamides. Bioorg Med Chem Lett. 2007;1 7(23): 6610–6614.
   Web of Science ®Google Scholar
• Isik, K.; Kocak F. O., Microbiol. Res., Available online 27 February 2007.
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Alyar S, Ozbek N, Karacan N. Synthesis and antimicrobial activity of new substituted arylsulfonamides. Drug Future. 2007; 32: 126–127 Suppl. A
   Web of Science ®Google Scholar
• Ozbek N, Alyar S, Karacan N. Synthesis, characterization and antimicrobial activity of new butanesulfonamides. Drug Future 2007; 32: 128 Suppl. A
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Google Scholar
• 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
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• Rastenyte, L.; Jokubaityte, S.; Mozolis, V., Lietuvos TSR Mokslu Akademijos Darbai, Serija B: Chemija, Technika, Fizine Geografija, 1974, 1, 69.
   Google Scholar
• Gajadhar-Plummer A S, Kahwa A, Mague J T. N,N0-Ethylenebis(p-toluenesulfonamide). Acta Crystallogr. Section E: 2001; E57(1): 68–69.
   Google Scholar
• 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.
   Google Scholar
• Friedman L, Litle R L, and Reichle W R.,p-toluensulfonylhydrazide. Org Syntheses. 1960;40:93.
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• Leo A J. Calculating log Poct from structures. Chem Rev. 1993; 93:1281–1306.
   Web of Science ®Google Scholar
• ALOGPS 2.1 software available at http://www.vcclab.org/lab/alogps.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• HyperChem 7.5 program, Hypercube Inc Toronto, Canada, 2002.
   Google Scholar
• http://www.talete.mi.it/ dragon_exp.htm, Italia
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• Wayne P A. National Committee for Clinical Laboratory Standards. Approved Standard M7-A4. 1997 and M27. 1997.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar