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

Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

12 Issues per year


IMPACT FACTOR 2016: 0.631

CiteScore 2017: 0.68

SCImago Journal Rank (SJR) 2017: 0.277
Source Normalized Impact per Paper (SNIP) 2017: 0.394

Online
ISSN
1865-7117
See all formats and pricing
More options …
Volume 73, Issue 6

Issues

Synthesis and antimicrobial evaluation of some heterocyclic compounds from 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes

El Sayed Ramadan
  • Corresponding author
  • Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21524, A. R. Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Essam M. Sharshira
  • Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21524, A. R. Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Ramadan I. El Sokkary
  • Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21524, A. R. Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Noussa Morsy
  • Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21524, A. R. Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2018-05-18 | DOI: https://doi.org/10.1515/znb-2018-0009

Abstract

A new series of chalcones, pyrazolinyl-pyrazoles, pyrazole-4-carbaldehyde oximes, pyrazole-4-carbonitriles, 5-pyrazolyl-1,2,4-triazolidine-3-thiones, and Knoevenagel condensation products was synthesized from 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes. Most reactions were carried out either without solvent or in the presence of water as a green solvent. The structure of synthesized compounds was characterized by spectral and elemental analysis. The synthesized compounds were tested in vitro for their antimicrobial activity against Escherichia coli, Staphylococcus aureus, and Candida albicans in comparison with imipenem (intravenous β-lactam antibiotic) and clotrimazole (antifungal medication) as reference drugs by using the agar diffusion technique. 3-Aryl-1-phenyl-1H-pyrazole-4-carbonitriles 8b, 8c, and 8d showed significant antifungal activity against the fungus C. albicans.

Keywords: antimicrobial activity; chalcones; green solvent; pyrazole-4-carbaldehyde; pyrazole-4-carbonitriles; solvent-free

References

  • [1]

    J. Lim, M. D. Altman, J. Baker, J. D. Brubaker, H. Chen, Y. Chen, M. A. Kleinschek, C. Li, D. Liu, J. K. F. Maclean, E. F. Mulrooney, J. Presland, L. Rakhilina, G. F. Smith, R. Yang, Bioorg. Med. Chem. Lett. 2015, 25, 5384.CrossrefGoogle Scholar

  • [2]

    V. Bavetsias, Y. Perez-Fuertes, P. J. Mcintyre, B. Atrash, M. Kosmopoulou, L. O’Fee, R. Burke, C. Sun, A. Faisal, K. Bush, S. Avery, A. Henley, F. I. Raynaud, S. Linardopoulos, R. Bayliss, J. Blagg, Bioorg. Med. Chem. Lett. 2015, 25, 4203.CrossrefGoogle Scholar

  • [3]

    S. Du, Z. Tian, D. Yang, X. Li, H. Li, C. Jia, C. Che, M. Wang, Z. Qin, Molecules 2015, 20, 8395.CrossrefGoogle Scholar

  • [4]

    S. Ghadbeigi, S. N. Ostad, A. Shafiee, M. Amini, Lett. Drug Des. Discov. 2015, 12, 754.CrossrefGoogle Scholar

  • [5]

    H. V. Chavan, B. P. Bandgar, L. K. Adsul, V. D. Dhakane, P. S. Bhale, V. N. Thakare, V. Masand, Bioorg. Med. Chem. Lett. 2013, 23, 1315.CrossrefGoogle Scholar

  • [6]

    S. Nishida, H. Maruoka, Y. Yoshimura, T. Goto, R. Tomita, E. Masumoto, F. Okabe, K. Yamagata, T. Fujioka, J. Heterocycl. Chem. 2012, 49, 303.CrossrefGoogle Scholar

  • [7]

    N. J. Thumar, M. P. Patel, Arkivoc 2009, xiii, 363.Google Scholar

  • [8]

    A. H. Abadi, A. A. Eissa, G. S. Hassan, Chem. Pharm. Bull. 2003, 51, 838.CrossrefGoogle Scholar

  • [9]

    A. I. Hashem, A. S. A. Youssef, K. A. Kandeel, W. S. I. Abou-Elmagd, Eur. J. Med. Chem. 2007, 42, 934.CrossrefGoogle Scholar

  • [10]

    P. T. Chovatia, J. D. Akabari, P. K. Kachhadia, P. D. Zalavadia, H. S. Joshi, J. Serb. Chem. Soc. 2007, 71, 713.Google Scholar

  • [11]

    P. Rathelot, N. Azas, H. El-Kashef, F. Delmas, C. D. Giorgio, P. Timon-David, J. Maldonado, P. Vanelle, Eur. J. Med. Chem. 2002, 37, 671.CrossrefGoogle Scholar

  • [12]

    M. B. Gawande, V. D. B. Bonifacio, R. Luque, P. S. Branco, R. S. Varma, Chem. Soc. Rev. 2013, 42, 5522.CrossrefGoogle Scholar

  • [13]

    E. M. Sharshira, N. M. M. Hamada, Molecules 2012, 17, 4962.CrossrefGoogle Scholar

  • [14]

    M. A. Kira, M. O. Abdel-Rahman, K. Z. Gadalla, Tetrahedron Lett. 1969, 10, 109.CrossrefGoogle Scholar

  • [15]

    O. Prakash, K. Pannu, A. Kumar, Molecules 2006, 11, 43.CrossrefGoogle Scholar

  • [16]

    M. Bernard, E. Hulley, H. Molenda, K. Stochla, U. Wrzeciono, Pharmazie 1986, 41, 560.Google Scholar

  • [17]

    N. V. Kavitha, K. Divekar, B. Priyadarshini, S. G. M. Manjunath, Der Pharma Chem. 2011, 3, 55.Google Scholar

  • [18]

    G. G. Kleinspehn, J. A. Jung, S. A. Studniarz, J. Org. Chem. 1967, 32, 460.CrossrefGoogle Scholar

  • [19]

    O. S. Attaryan, A. A. Sahakyan, R. A. Tamazyan, A. G. Ayvazyan, G. V. Asratyan, Russ. J. Gen. Chem. 2012, 82, 1720.CrossrefGoogle Scholar

  • [20]

    E. Buehler, G. B. Brown, J. Org. Chem. 1967, 32, 261.CrossrefGoogle Scholar

  • [21]

    J. D. Patil, D. M. Pore, RSC Adv. 2014, 4, 14314.CrossrefGoogle Scholar

  • [22]

    M. M. Mane, D. M. Pore, Tetrahedron Lett. 2014, 55, 6601.CrossrefGoogle Scholar

  • [23]

    D. M. Pore, P. G. Hegade, M. M. Mane, J. D. Patil, RSC Adv. 2013, 3, 25723.CrossrefGoogle Scholar

  • [24]

    R. Ramesh, A. Lalitha, RSC Adv. 2015, 5, 51188.CrossrefGoogle Scholar

  • [25]

    A. Karlsson, K. Parsmyr, E. Sandstrom, E. M. Fenyo, J. Albert, J. Clin. Microbiol. 1994, 32, 364.Google Scholar

  • [26]

    Z. Schelz, J. Molnar, J. Hohmann, Fitoterapia 2006, 7, 279.Google Scholar

  • [27]

    O. Prakash, K. Pannu, R. Naithani, Synth. Commun. 2006, 36, 3479.CrossrefGoogle Scholar

  • [28]

    O. Prakash, R. Pundeer, P. Ranjan, K. Pannu, Y. Dhingra, K. R. Aneja, Indian J. Chem. 2009, 48B, 563.Google Scholar

  • [29]

    G. J. Reddy, S. Sailaja, K. Pallavi, K. S. Rao, Indian J. Chem. 2005, 44B, 180.Google Scholar

About the article

Received: 2018-01-07

Accepted: 2018-04-22

Published Online: 2018-05-18

Published in Print: 2018-06-27


Citation Information: Zeitschrift für Naturforschung B, Volume 73, Issue 6, Pages 389–397, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0009.

Export Citation

©2018 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Comments (0)

Please log in or register to comment.
Log in