2,632
Views
23
CrossRef citations to date
0
Altmetric
Research Article

Design, synthesis, antimicrobial evaluation and molecular docking studies of some new 2,3-dihydrothiazoles and 4-thiazolidinones containing sulfisoxazole

, &
Pages 236-246 | Received 12 Dec 2014, Accepted 26 Jan 2015, Published online: 27 Mar 2015

References

  • Tenover FC, McDonald LC. Vancomycin-resistant staphylococci and enterococci: epidemiology and control. Curr Opin Infect Dis 2005;18:300–5
  • Jsturiz RE. Optimizing antimicrobial prescribing. Int J Antimicrob Agents 2010;36:S19–22
  • Chen J, Luo Y, Zhang S, et al. Community-acquired necrotizing pneumonia caused by methicillin-resistant Staphylococcus aureus producing Panton–Valentine leukocidin in a Chinese teenager: case report and literature review. Inter J Infect Dis 2014;26:17–21
  • Grabsch EA, Mahony AA, Cameron DRM, et al. Significant reduction in vancomycin-resistant enterococcus colonization and bacteraemia after introduction of a bleach-based cleaning-disinfection programme. J Hosp Infect 2012;82:234–42
  • Chong Y, Shimoda S, Yakushiji H, et al. Fatal candidemia caused by azole-resistant Candida tropicalis in patients with hematological malignancies. J Infect Chemother 2012;18:741–6
  • Wells CD, Cegielski JP, Nelson LJ, et al. HIV infection and multidrug-resistant tuberculosis: the perfect storm. J Infect Dis 2007;196:S86–107
  • Khan MW, Alam MJ, Rashid MA, Chowdhury R. A new structural alternative in benzo[b]furans for antimicrobial activity. Bioorg Med Chem 2005;13:4796–805
  • Tan Y-T, Tillett DJ, McKay IA. Molecular strategies for overcoming antibiotic resistance in bacteria. Mol Med Today 2000;6:309–14
  • Bremner JB, Ambrus JI, Samosorn S. Dual action-based approaches to antibacterial agents. Curr Med Chem 2007;14:1459–77
  • Zoumpoulakis P, Camoutsis C, Pairas G, et al. Synthesis of novel sulfonamide-1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, as potential antibacterial and antifungal agents. Biological evaluation and conformational analysis studies. Bioorg Med Chem 2012;20:1569–83
  • Sławiński J, Szafrański K, Vullo D, Supuran CT. Carbonic anhydrase inhibitors. Synthesis of heterocyclic 4-substituted pyridine-3-sulfonamide derivatives and their inhibition of the human cytosolic isozymes I and II and transmembrane tumor-associated isozymes IX and XII. Eur J Med Chem 2013;69:701–10
  • Isik S, Kockar F, Aydin M, et al. Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates. Bioorg Med Chem 2009;17:1158–62
  • Zhao Z, Wolkenberg SE, Lu M, et al. Novel indole-3-sulfonamides as potent HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs). Bioorg Med Chem Lett 2008;18:554–9
  • Vullo D, Leewattanapasuk W, Mühlschlegel FA, et al. Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides. Bioorg Med Chem Lett 2013;23:2647–52
  • Kamal A, Dastagiri D, Ramaiah MJ, et al. Synthesis and apoptosis inducing ability of new anilino substituted pyrimidine sulfonamides as potential anticancer agents. Eur J Med Chem 2011;46:5817–24
  • Bano S, Javed K, Ahmad S, et al. Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents. Eur J Med Chem 2011;46:5763–8
  • Argyropoulou I, Geronikaki A, Vicini P, Zani F. Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents. Arkivoc 2009;6:89–102
  • Yun MK, Wu Y, Li Z, et al. Catalysis and sulfa drug resistance in dihydropteroate synthase. Science 2012;335:1110–14
  • Anand N, Remers WA. Synthetic antibacterial agents. In: Abraham DJ, ed. Burger's medicinal chemistry and discovery. Vol. 5, 5th ed. New York: Wiley and Sons; 2003:557–82
  • Tripathi AC, Gupta SJ, Fatima GN, et al. 4-Thiazolidinones: the advances continue…. Eur J Med Chem 2014;72:52–77
  • Bondock S, Khalifa W, Fadda AA. Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur J Med Chem 2007;42:948–54
  • Bondock S, Naser T, Ammar YA. Synthesis of some new 2-(3-pyridyl)-4,5-disubstituted thiazoles as potent antimicrobial agents. Eur J Med Chem 2013;62:270–9
  • Ried W, Meyer A. Über die verwendung von cyanacethydrazid zur darstellung von stickstoffheterocyclen. I. eine einfache synthese von N-amino-α-pyridonen. Chem Ber 1957;90:2841–8
  • Nasr T, Bondock S, Eid S. Design, synthesis, antimicrobial evaluation and molecular docking studies of some new thiophene, pyrazole and pyridone derivatives bearing sulfisoxazole moiety. Eur J Med Chem 2014;84:491–504
  • Shamroukh AH, Zaki MEA, Morsy EMH, et al. Synthesis, isomerization, and antimicrobial evaluation of some pyrazolopyranotriazolopyrimidine derivatives. Arch Pharm Chem Life Sci 2007;340:345–51
  • Molecular Operating Environment (MOE), 2013.08, Chemical Computing Group Inc., 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7, 2013
  • Naïm M, Bhat S, Rankin KN, et al. Solvated interaction energy (SIE) for scoring protein–ligand binding affinities. 1. Exploring the parameter space. J Chem Inf Model 2007;47:122–33
  • Clark AM, Labute P. 2D depiction of protein−ligand complexes. J Chem Inf Model 2007;47:1933–44
  • Gewald VK. Heterocyclen aus CH-aciden nitrilen. VI. Reaktion von methylenaktiven Nitrilen mit Senfölen und Schwefel. J Prakt Chem 1966;32:26–30
  • Kaminskyy D, Gzella AK, Lesyk R. Cyclocondensation of thioamides and haloacetic acid derivatives provides only 4-thiazolidinones; isomeric 5-thiazolidinones were not observed. Synth Commun 2014;44:231–6
  • Metwally M, Abdel-Latif E, Bondock S. Thiocarbamoyl derivatives as synthons in heterocyclic synthesis. J Sulfur Chem 2007;28:431–66
  • Bock L, Miller GH, Schaper KJ, Seydel JK. Sulfonamide structure–activity relations in a cell-free system. 2. Proof for the formation of a sulfonamide-containing folate analog. J Med Chem 1974;17:23–8
  • Roland S, Ferone R, Harvey RJ, et al. The characteristics and significance of sulfonamides as substrates for Escherichia coli dihydropteroate synthase. J Biol Chem 1979;254:10337–45

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.