European Journal of Chemistry 2013, 4(4), 454-458. doi:10.5155/eurjchem.4.4.454-458.784

Green synthesis of novel pyrazole containing Schiff base derivatives as antibacterial agents on the bases of in-vitro and DFT


Salman Ahmad Khan (1,*) , Abdullah Mohamed Asiri (2) , Abdulrhim Alabbas Basheike (3) , Kamlesh Sharma (4)

(1) Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
(2) Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
(3) Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
(4) Molecular Science Research Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
(*) Corresponding Author

Received: 25 Mar 2013, Accepted: 07 May 2013, Published: 31 Dec 2013

Abstract


A series of pyrazole containing Schiff bases were synthesized, by the reaction of 3,5-dimethyl-1-phenylpyrazole-4-carboxaldehyde and the corresponding active amines under microwave irradiation. The structures of the synthesized compounds were established by spectroscopic data (FT-IR, 1H NMR, 13C NMR and ESI-MS) and elemental analyses. The anti-bacterial activity of these compounds were tested in vitro by the disc diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration using chloramphenicol as reference drug. All the molecules were modeled and optimized by using density functional theory, DFT/B3LYP method. Calculated descriptors, the lower unoccupied molecular orbital and the density were used to interpret the antibacterial activity of the compounds. The results showed that compound 3 is better inhibitor of both types of test bacteria as compared to chloramphenicol.

4_4_454_458

Keywords


Pyrazole; Schiff bases; Chloramphenicol; Antibacterial activity; Density functional theory; Minimum inhibitory concentration

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.4.4.454-458.784

Get Citation | Scilit | GrowKudos | ResearchGate | Publons | Microsoft Academic

WorldCat | Dimensions | SemanticScholar | PlumX Metrics | Kopernio | Zotero | Mendeley

Article Metrics


This Abstract was viewed 1162 times | PDF Article downloaded 496 times


Citations

/


[1]. S. M. Afzal, M. A. N. Razvi, Salman A. Khan, Osman I. Osman, Ahmed H. Bakry, Abdullah M. Asiri, Oksana Ostroverkhova
Physicochemical and Nonlinear Optical Properties of Novel Environmentally Benign Heterocyclic Azomethine Dyes: Experimental and Theoretical Studies
PLOS ONE  11(9), e0161613, 2016
DOI: 10.1371/journal.pone.0161613
/


[2]. Marie-Hélène Tremblay, Thomas Skalski, Yohan Gautier, Grégory Pianezzola, W. G. Skene
Investigation of Triphenylamine–Thiophene–Azomethine Derivatives: Toward Understanding Their Electrochromic Behavior
The Journal of Physical Chemistry C  120(17), 9081, 2016
DOI: 10.1021/acs.jpcc.6b01675
/


[3]. Salman A. Khan, Abdullah M. Asiri, Hadi Mussa Basisi
Synthesis, Single X-ray Crystal, Spectroscopic and Photophysical Studies of Novel Heterocyclic Chalcones with Their Biological Application
Journal of Fluorescence  25(4), 825, 2015
DOI: 10.1007/s10895-015-1543-z
/


[4]. Niloufar Dorosti, Farzaneh Afshar, Fatemeh Ghaziani, Khodayar Gholivand, Sanaz Zarabi
Two Hg(II) complexes of 4-pyridinecarbacylamidophosphates: Synthesis, crystal structures, theoretical studies and in vitro antibacterial evaluation
Inorganica Chimica Acta  489, 140, 2019
DOI: 10.1016/j.ica.2019.01.038
/


[5]. Salman A. Khan, Abdullah M. Asiri, Saad H. Al-Thaqafy, Hassan M. Faidallah, Samy A. El-Daly
Synthesis, characterization and spectroscopic behavior of novel 2-oxo-1,4-disubstituted-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile dyes
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy  133, 141, 2014
DOI: 10.1016/j.saa.2014.05.013
/


[6]. Alireza Hasaninejad, Sanaz Mojikhalifeh, Maryam Beyrati
Highly efficient, catalyst-free, one-pot, pseudo five-component synthesis of novel pyrazoline-containing Schiff bases, metal complexes formation and computational studies via DFT method
Applied Organometallic Chemistry  32(7), e4380, 2018
DOI: 10.1002/aoc.4380
/


References

[1]. Dore, J. C.; Lacroix, R. Eur. J. Med. Chem. 1987, 22, 109-117.
http://dx.doi.org/10.1016/0223-5234(87)90004-3

[2]. Johnson, P. J. Parasitol. Today 1993, 9, 183-186.
http://dx.doi.org/10.1016/0169-4758(93)90143-4

[3]. Zhang, W.; Berberoy, E. M.; Freeling, J.; He, D.; Moxley, R. A.; Francis, D. H. Infect. Immunol. 2006, 74, 3107-3114.
http://dx.doi.org/10.1128/IAI.01338-05
PMid:16714538 PMCid:PMC1479275

[4]. Pfaller, M. A.; Jones, N. R.; Doern, V. G.; Sader, S. H.; Kugler, C. K.; Beach, L. M. Diagn. Microbiol. Infect. Dis. 1999, 33, 283-297.
http://dx.doi.org/10.1016/S0732-8893(98)00149-7

[5]. Sternbach, H.; State, R. Harv. Rev. Psychiatry. 1997, 5(4), 214-226.
http://dx.doi.org/10.3109/10673229709000304
PMid:9427014

[6]. Abunada, N. M.; Hassaneen, H. M.; Kandile, N. G.; Miqdad, O. A. Molecules 2008, 13, 1501-1517.
http://dx.doi.org/10.3390/molecules13071501
PMid:18719521

[7]. Reddy, C. S.; Devi, M. V.; Kumar, G. R.; Rao, L. S.; Nagaraj, A. Ind. J. Chem. 2011, 50B, 1181-1186.

[8]. Anandarajagopal, K.; Sunilson, J. A. J.; Illavarasu, A.; Thangavelpandian, N.; Kalirajan, R. Int. J. Chem. Tech Res. 2010, 2(1), 45-49.

[9]. Ahsan, M. J.; Samy, J. G.; Khalilullah, H.; Bakht, M. A.; Hassan, M. Z. Eur. J. Med. Chem. 2011, 46, 5694-5697.
http://dx.doi.org/10.1016/j.ejmech.2011.09.035
PMid:21978838

[10]. Yang, J.; Cao, H.; Liu, H.; Lia, B.; Maa, Y. J. Chine. Chem. Soc. 2011, 58, 369-375.

[11]. Southan, G. J.; Gauld, D.; Lubeskie, A.; Zingarelli, B.; Cuzzocrea, S.; Salzman, A. L.; Szabo, C.; Wolff, D. J. Biochem. Pharma. 1997, 54, 409-417.
http://dx.doi.org/10.1016/S0006-2952(97)00196-2

[12]. Karthikeyan, T.; Seelan, V.; Lalitha, K. G.; Perumal, P. T. Bioorg. Med. Chem. 2009, 19, 3370-3373.
http://dx.doi.org/10.1016/j.bmcl.2009.05.055
PMid:19481931

[13]. Abdel-Aziz, M.; El-Din, G.; Abuo-Rahma, A.; Hassan, A. A. Eur. J. Med. Chem. 2009, 44, 3480-3487.
http://dx.doi.org/10.1016/j.ejmech.2009.01.032
PMid:19268406

[14]. Bekhit, A. A.; Ashour, H. M. A.; Guemei, A. A. Arch. Pharm. Chem. Life Sci. 2005, 338, 167−174.
http://dx.doi.org/10.1002/ardp.200400940
PMid:15864786

[15]. Arbaciauskiene, E.; Kazlauskas, K.; Miasojedovas, A.; Jursenas, S.; Jankauskas, V.; Holzer, W.; Getautis, V.; Sackus, A. Dyes Pigments, 2010, 85, 79-85.
http://dx.doi.org/10.1016/j.dyepig.2009.10.007

[16]. Clays, K.; Coe, B. J. Chem. Mater. 2003, 15 (3), 642-648.
http://dx.doi.org/10.1021/cm0212111

[17]. Kucybala, Z.; Pyszka, I.; Paczkowski, J. J. Chem. Soc., Perkin Trans. 2000, 2, 1559-1567.

[18]. Asiri, A. M.; Khan, S. A. Molecules, 2010, 15, 6850-6858.
http://dx.doi.org/10.3390/molecules15106850
PMid:20938399

[19]. Dedeian, K.; Shi, J.; Shepherd, N.; Forsythe, E.; Morton, D. C. Inorg. Chem. 2005, 44 (13), 4445-4447.
http://dx.doi.org/10.1021/ic050324u
PMid:15962944

[20]. Asiri, A. M.; Khan, S. A. Molecules 2010, 15, 4784-4791.
http://dx.doi.org/10.3390/molecules15074784
PMid:20657393

[21]. Penta, S.; Vedula, R. R. Org. Commun. 2012, 5, 143-149.

[22]. Parikh, K. S.; Vyas, S. P. J. Chem. Pharm. Res. 2012, 4, 2681-2683.

[23]. Sunil, D.; Isloor, A. M.; Shetty, P.; Chandrakantha, B.; Satyamoorthy, K. Med. Chem. Res. 2011, 20, 1024-1032.
http://dx.doi.org/10.1007/s00044-010-9433-z

[24]. Youssef, A. M.; Neeland, E. G.; Villanueva, E. B.; White, M. S.; El-Ashmawy, I. M.; Klegeris, B. A.; Abd-El-Aziz, A. S. Biorg. Med. Chem. 2010, 18, 5685-5696.
http://dx.doi.org/10.1016/j.bmc.2010.06.018
PMid:20609589

[25]. Ratkovic, Z.; Juranic, Z. D.; Stanojkovic, T.; Manojlovic, D.; Vukicevic, R. D.; Radulovic, N.; Joksovic, M. D. Bioorg. Chem. 2010, 38, 26-32.
http://dx.doi.org/10.1016/j.bioorg.2009.09.003
PMid:19846191

[26]. Asiri, A. M. Molbank 2003, 2003(3), M341.
http://dx.doi.org/10.3390/M341

[27]. Abdul-Rahman, R. M. Pharmazie 2001, 56, 275-284.

[28]. Sharma, K.; Lal, B. J. Steroid Biochem. Mol. Biol. 2008, 110, 278-283.

[29]. Sharma, K.; Mishra, S. B.; Mishra, A. K. Spectrochim. Acta A 2011, 79, 1493-1498.
http://dx.doi.org/10.1016/j.saa.2011.05.005
PMid:21684196

[30]. Marwani, H.; Asiri, A. M.; Khan, S. A. Russ. J. Bioorg. Chem. 2012, 38, 533-538.
http://dx.doi.org/10.1134/S1068162012050056

[31]. Khan, S. A.; Asiri, A. M. Chin. J. Chem. 2012, 30, 1901-1905.
http://dx.doi.org/10.1002/cjoc.201200126

[32]. Spartan'04 Version 1.0.3, Wavefunction, Inc. 18401 Von Karman Ave., Suite 370, Irvine, CA 92612, USA.


How to cite


Khan, S.; Asiri, A.; Basheike, A.; Sharma, K. Eur. J. Chem. 2013, 4(4), 454-458. doi:10.5155/eurjchem.4.4.454-458.784
Khan, S.; Asiri, A.; Basheike, A.; Sharma, K. Green synthesis of novel pyrazole containing Schiff base derivatives as antibacterial agents on the bases of in-vitro and DFT. Eur. J. Chem. 2013, 4(4), 454-458. doi:10.5155/eurjchem.4.4.454-458.784
Khan, S., Asiri, A., Basheike, A., & Sharma, K. (2013). Green synthesis of novel pyrazole containing Schiff base derivatives as antibacterial agents on the bases of in-vitro and DFT. European Journal of Chemistry, 4(4), 454-458. doi:10.5155/eurjchem.4.4.454-458.784
Khan, Salman, Abdullah Mohamed Asiri, Abdulrhim Alabbas Basheike, & Kamlesh Sharma. "Green synthesis of novel pyrazole containing Schiff base derivatives as antibacterial agents on the bases of in-vitro and DFT." European Journal of Chemistry [Online], 4.4 (2013): 454-458. Web. 8 Dec. 2019
Khan, Salman, Asiri, Abdullah, Basheike, Abdulrhim, AND Sharma, Kamlesh. "Green synthesis of novel pyrazole containing Schiff base derivatives as antibacterial agents on the bases of in-vitro and DFT" European Journal of Chemistry [Online], Volume 4 Number 4 (31 December 2013)

DOI Link: https://doi.org/10.5155/eurjchem.4.4.454-458.784

| | | | |

| | | | | |

. OPEN ACCESS PEER-REVIEWED Research Article

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.