Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Zeitschrift für Naturforschung C

A Journal of Biosciences

Editor-in-Chief: Seibel, Jürgen

Editorial Board: Aigner , Achim / Boland, Wilhelm / Bornscheuer, Uwe / Hoffmann, Klaus

12 Issues per year

IMPACT FACTOR 2017: 0.882
5-year IMPACT FACTOR: 0.912

CiteScore 2017: 0.92

SCImago Journal Rank (SJR) 2017: 0.288
Source Normalized Impact per Paper (SNIP) 2017: 0.448

See all formats and pricing
More options …
Volume 70, Issue 1-2


Synthesis and antimicrobial properties of N-substituted derivatives of (E)-2′,3″-thiazachalcones

Asu Usta
  • Corresponding author
  • Faculty of Arts and Sciences, Department of Chemistry, Recep Tayyip Erdogan University, 53100 Rize, Turkey
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Hacer Taşkıran
  • Faculty of Arts and Sciences, Department of Biology, Recep Tayyip Erdogan University, 53100 Rize, Turkey
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2015-03-27 | DOI: https://doi.org/10.1515/znc-2014-4182


N-alkyl substituted 2′,3″-thiazachalcones {3-[(1E)-3-(4-methylthiophene-2-yl)-3-oxoprop-1-en-1-yl]-1-alkyl (C5–12,14) pyridinium bromides} were synthesized by a two-step reaction. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, elemental analysis and mass spectral studies. The synthesized compounds were tested for antibacterial activities and found to be more active against Gram-positive as compared to Gram-negative bacteria.

Keywords: antimicrobial activity; azachalcone; N-alkyl azachalconium bromide


  • 1.

    Harborne JB. The flavonoids: advances in research. London: Chapman & Hall, 1998.Google Scholar

  • 2.

    Liu XL, Xu YJ, Go ML. Functionalized chalcones with basic functionalities have antibacterial activity against drug sensitive Staphylococcus aureus. Eur J Med Chem 2008;43:1681–7.PubMedWeb of ScienceCrossrefGoogle Scholar

  • 3.

    Sharma A, Chakravarti B, Gupt MP, Siddiquin JA, Konwar R, Tripathi RP. Synthesis and anti breast cancer activity of biphenyl based chalcones. Bioorg Med Chem 2010;18:4711–20.PubMedCrossrefGoogle Scholar

  • 4.

    Xia Y, Yang ZY, Xia P, Bastow KF, Nakanishi Y, Lee KH. Antitumor agents. Part 202: novel 2′-amino chalcones: design, synthesis and biological evaluation. Bioorg Med Chem Lett 2000;10: 699–701.Google Scholar

  • 5.

    Ahmad MR, Sastry VG, Bano N. Antibacterial and antioxidant activities of some novel chalcone derivatives. J Pharm Res 2011;4:2347–9.Google Scholar

  • 6.

    Roman BI, Ryck TD, Dierickx L, Vanhoecke BW, Katritzky AR, Bracke M, et al. Exploration of the SAR of anti-invasive chalcones: synthesis and biological evaluation of conformationally restricted analogues. Bioorg Med Chem 2012;20:4812–9.PubMedCrossrefGoogle Scholar

  • 7.

    Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem 2007;42:125–37.CrossrefPubMedWeb of ScienceGoogle Scholar

  • 8.

    Nowakowska Z, Kedzia B, Schroeder G. Synthesis, physicochemical properties and antimicrobial evaluation of new (E)-chalcones. Eur J Med Chem 2008;43:707–13.CrossrefPubMedGoogle Scholar

  • 9.

    Nowakowska Z, Wyrzykiewicz E, Kedzia B. Synthesis and antimicrobial properties of N-substituted derivatives of (E)-4-azachalcones. Il Farmaco 2001;56:325–9.CrossrefGoogle Scholar

  • 10.

    Nowakowska Z, Wyrzykiewicz E, Kedzia B. Antimicrobial activity of some N-alkyl substituted of (E)-4-azachalconium and (E)-3′-hydroxy-4-azachalconium bromides. Il Farmaco 2002;57:657–61.CrossrefGoogle Scholar

  • 11.

    Nowakowska Z. 1H and 13C NMR chemical shift assignment of some N-bromoalkyl-(E)-4-azachalcone bromides. Magn Reson Chem 2000;38:382–3.CrossrefGoogle Scholar

  • 12.

    Yaylı N, Üçüncü O, Yaşar A, Küçük M, Yaylı N, Akyüz E, et al. Synthesis and biological activities of N-alkyl derivatives of o-, m-, and p-nitro (E)-4-azachalcones and stereoselective photochemistry in solution, with theoretical calculations. Turk J Chem 2006;30:505–14.Google Scholar

  • 13.

    Yaylı N, Üçüncü O, Yaşar A, Yaylı N, Burnaz NA, Karaoğlu ŞA, et al. Photochemistry of nitro-substituted (E)-2-azachalcones with theoretical calculations and biological activities. J Photochem Photobiol A: Chem 2009;203:85–91.CrossrefWeb of ScienceGoogle Scholar

  • 14.

    Yaylı N, Mısır G, Yaylı N, Yaşar A, Demir E, Demirbağ Z. Synthesis and antimicrobial activity of N-alkyl substituted p-methyl (E)-3- and 4-azachalconium bromides. Turk J Chem 2010;34:219–28.Web of ScienceGoogle Scholar

  • 15.

    Opletalova V, Hartly J, Patel A, Palat K, Buchta V. Ring substituted 3-phenyl-1-(2-pyrazinyl)-2-propen-1-ones as potential photosynthesis-inhibiting, antifungal and antimycobacterial agents. Il Farmaco 2002;57:135–44.CrossrefGoogle Scholar

  • 16.

    Usta A, Yaşar A, Yılmaz N, Güleç C, Yaylı N, Karaoğlu ŞA, et al. Synthesis, configuration, and antimicrobial properties of novel substituted and cyclized 2′,3″-thiazachalcones. Helv Chim Acta 2007;90:1482–90.Web of ScienceCrossrefGoogle Scholar

  • 17.

    Usta A, Yaşar A, Yaylı N, Karaoğlu şA, Yaylı N. Synthesis of methyl (E)-2′, 4″-thiazachalcones and their N-alkyl derivatives, photochemistry with theoretical calculations and antimicrobial activities., Turk J Chem 2009;33:621–32.Web of ScienceGoogle Scholar

  • 18.

    Thapa P, Karki R, Basnet A, Thapa U, Choi H, Na Y, et al. 2,6-Dithienyl-4-arylpyridines: synthesis, topoisomerase I and II inhibition and structure-activity relationship. Bull Korean Chem Soc 2008;29:1605–8.Google Scholar

  • 19.

    Dubey PK, Naidu A, Kumar CR, Prasada Reddy PV. Preparation of 4-(1-alkyl-benzo[d]imidazole-2-yl)-2-phenyl-2,3-dihydrobenzo(b)[1,4]thiazepines. Indian J Chem Sect B: Org Chem Incl Med Chem 2003;42B:1701–5.Google Scholar

  • 20.

    Raghav N, Jangra S, Singh M, Kaur R, Rohilla A. In-vitro studies of some chalcones on alkaline phosphatase. Int J Pharm Pharm Sci 2012;4:288–92.Google Scholar

  • 21.

    Budhiraja A, Kadian K, Kaur M, Aggarwal V, Garg A, Sapra S, et al. Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents. Med Chem Res 2012;21:2133–40.CrossrefGoogle Scholar

  • 22.

    Rateb NM, Zohdi HF. Atom-efficient, solvent-free, green synthesis of chalcones by grinding. Synthetic Comm 2009;39:2789–94.CrossrefGoogle Scholar

  • 23.

    Basnet A, Thapa P, Karki R, Na Y, Jahng Y, Jeong BS, et al. 2,4,6-Trisubstituted pyridines: synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship. Bioorg Med Chem 2007;15:4351–9.CrossrefPubMedGoogle Scholar

  • 24.

    Sıvakumar PM, Geetha babu SK, Mukesh D. QSAR studies on chalcones and flavonoids as anti-tuberculosis agents using genetic function approximation (GFA) method. Chem Pharm Bull 2007;55:44–9.PubMedCrossrefWeb of ScienceGoogle Scholar

  • 25.

    Awasthi SK, Mishra N, Kumar B, Sharma M, Bhattacharya A, Mishra LC, et al. Potent antimalarial activity of newly synthesized substituted chalcone analogs in vitro. Med Chem Res 2009;18:407–20.CrossrefGoogle Scholar

  • 26.

    Yaylı N, Küçük M, Üçüncü O, Yaşar A, Yaylı N, Karaoğlu ŞA. Synthesis of N-alkyl derivatives and photochemistry of nitro (E)-3-azachalcones with theoretical calculations and biological activities. J Photochem Photobiol A: Chem 2007;188:161–8.CrossrefWeb of ScienceGoogle Scholar

  • 27.

    Woods GL, Brown-Elliott BA, Desmond EP, Hall GS, Heifets L, Pfyffer GE, et al. Susceptibility testing of mycobacteria, nocardiae, and other aerobic actinomycetes; approved standard. NCCLS document M24-A. 23 (18), 2003.Google Scholar

About the article

Corresponding author: Asu Usta, Faculty of Arts and Sciences, Department of Chemistry, Recep Tayyip Erdogan University, 53100 Rize, Turkey, Tel.: +90-464-2236126 Fax: +90-464-2234019, (office), E-mail:

Received: 2014-10-16

Revised: 2015-02-27

Accepted: 2015-03-04

Published Online: 2015-03-27

Published in Print: 2015-01-01

Citation Information: Zeitschrift für Naturforschung C, Volume 70, Issue 1-2, Pages 45–50, ISSN (Online) 1865-7125, ISSN (Print) 0939-5075, DOI: https://doi.org/10.1515/znc-2014-4182.

Export Citation

©2015 by De Gruyter.Get Permission

Comments (0)

Please log in or register to comment.
Log in