European Journal of Chemistry 2014, 5(1), 85-90. doi:10.5155/eurjchem.5.1.85-90.789

Green synthesis, antibacterial activity and computational study of pyrazoline and pyrimidine derivatives from 3-(3,4-dimethoxy-phenyl-1-(2,5-dimethyl-thiophen-3-yl)-propenone


Salman Ahmad Khan (1,*) , Abdullah Mohamed Asiri (2) , Sanjay Kumar (3) , Kamlesh Sharma (4)

(1) Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
(2) Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah 21589, Saudi Arabia
(3) Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India
(4) Molecular Science Research Institute, School of Chemistry, University of the Witwatersrand, Johannesburg, South Africa
(*) Corresponding Author

Received: 02 Apr 2013, Accepted: 07 May 2013, Published: 31 Mar 2014

Abstract


Various pyrazoline and pyrimidine derivatives were synthesized by the reaction of thiosemicarbazide / phenyl hydrazine / hydrazine hydtate / thiourea / urea with 3-(3,4-dimethoxy-phenyl-1-(2,5-dimethyl-thiophen-3-yl)-propenone under microwave irradiation, which itself was derived from the reaction of 3-acetyl-2,5-dimethylthiophene with 3,4-dimethoxy benzaldehyde. The corresponding pyrazoline and pyrimidine derivatives were obtained in good to excellent yields. All of the new compounds obtained were characterized by IR, 1H NMR, 13C NMR, MS and elemental analyses. The anti-bacterial activity of these compounds were tested in-vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria. The results showed that one of the pyrazoline derivatives is better at inhibiting the growth as compared to chloramphenicol against both types of the bacteria (Gram-positive and Gram-negative). Furthermore, all the molecules were subjected to computational calculation using the density functional theory with B3LYP method to corroborate their antibacterial activities.


Keywords


Pyrazoline; Pyrimidine; Antibacterial; Chloramphenicol; Density functional theory; 3-(3,4-Dimethoxy-phenyl-1-(2,5-dimethyl-thiophen-3-yl)-propenone

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.1.85-90.789

Article Metrics


This Abstract was viewed 1277 times | PDF Article downloaded 545 times

Citations

/


[1]. Mahmoud Chebbah, Amel Messai, Duygu Bilge, Ahcen Bouchemma, Cemal Parlak
New unsymmetrically substituted triazacyclohexanes: Synthesis, characterisation, antimicrobial properties and DFT study
Journal of Molecular Structure  1129, 152, 2017
DOI: 10.1016/j.molstruc.2016.09.060
/


[2]. Mohammad Mahmoud Ibrahim
Synthesis and characterization of new 3,5-disubstituted-4,5-dihydro-1H-pyrazole and their carbothioamide derivatives
European Journal of Chemistry  6(1), 78, 2015
DOI: 10.5155/eurjchem.6.1.78-83.1148
/


[3]. Assia Sid, Amel Messai, Cemal Parlak, Nadide Kazancı, Dominique Luneau, Gürkan Keşan, Lydia Rhyman, Ibrahim A. Alswaidan, Ponnadurai Ramasami
1-Formyl-3-phenyl-5-(4-isopropylphenyl)-2-pyrazoline: Synthesis, characterization, antimicrobial activity and DFT studies
Journal of Molecular Structure  1121, 46, 2016
DOI: 10.1016/j.molstruc.2016.05.043
/


[4]. Maysoon Mohammed Almahdi, Ahmed Elsadig Mohammed Saeed, Nadia Hanafy Metwally
Synthesis and antimicrobial activity of some new pyrazoline derivatives bearing sulfanilamido moiety
European Journal of Chemistry  10(1), 30, 2019
DOI: 10.5155/eurjchem.10.1.30-36.1791
/


[5]. Salman A. Khan, Abdullah M. Asiri, Mohie E. M. Zayed, Humaira Parveen, Faisal M. S. Aqlan, Kamlesh Sharma
Microwave-assisted Synthesis, Characterization, and Density Functional Theory Study of Biologically Active Ferrocenyl Bis-pyrazoline and Bis-pyrimidine as Organometallic Macromolecules
Journal of Heterocyclic Chemistry  56(1), 312, 2019
DOI: 10.1002/jhet.3381
/


[6]. Abdullah M. Asiri, Salman A. Khan, Hadi Mussa Basisi
Single X-ray crystal and spectroscopic investigation of novel biologically active donor–acceptor chalcones as specific application for opto-electronics and photonics
Journal of the Taiwan Institute of Chemical Engineers  59, 457, 2016
DOI: 10.1016/j.jtice.2015.07.020
/


[7]. 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
/


[8]. Salman A. Khan, Abdullah M. Asiri, Khalid Al-Amry, Maqsood Ahmad Malik
Synthesis, Characterization, Electrochemical Studies, andIn VitroAntibacterial Activity of Novel Thiosemicarbazone and Its Cu(II), Ni(II), and Co(II) Complexes
The Scientific World Journal  2014, 1, 2014
DOI: 10.1155/2014/592375
/


References

[1]. Kachadourian, R.; Day, B. J.; Pugazhenti, S.; Franklin, C. C.; Bastide, E. G.; Mahaffey, G.; Gauthier, C.; Pietro, A. D.; Boumendjel, A. J. Med. Chem. 2012, 55, 1382-1388.
http://dx.doi.org/10.1021/jm2016073

[2]. Shi, S. P.; Wanibuchi, K.; Morita, H.; Endo, K.; Noguchi, H.; Abe, I. Org. Lett. 2009, 11, 551-554.
http://dx.doi.org/10.1021/ol802606w

[3]. Pasquale, G.; Romanelli, G. P.; Autino, J. C.; Garcia, J.; Ortiz, E. V.; Duchowicz, P. R. J. Agric. Food Chem. 2012, 60, 692-697.
http://dx.doi.org/10.1021/jf203374r

[4]. Gaikwad, P. Priyadarsini, K. I. Naumov, S. Rao, B. S. M. J. Phys. Chem. 2010, 114, 7877-7885.
http://dx.doi.org/10.1021/jp103382x

[5]. Narender, T.; Venkateswarlu, K.; Nayak, B. V.; Sarkar, S. Tetrahedron Lett. 2011, 52, 5794-5798.
http://dx.doi.org/10.1016/j.tetlet.2011.08.120

[6]. Zhang, Y.; Li, X.; Li, J.; Chen, J.; Meng, X.; Zhao, M.; Chen, B. Org. Lett. 2012, 14, 26-29.
http://dx.doi.org/10.1021/ol202718d

[7]. Liu, X. F.; Zheng, C. J.; Sun, L. P.; Liu, X. K.; Piao, H. R. Eur. J. Med. Chem. 2011, 46, 3469-3473.
http://dx.doi.org/10.1016/j.ejmech.2011.05.012

[8]. Sugamoto, K.; Matsusita, Y. I.; Matsui, K.; Kurogi, C.; Matsui, T. Tetrahedron 2011, 67, 5346-5359.
http://dx.doi.org/10.1016/j.tet.2011.04.104

[9]. Zheng, C. J.; Sun, L. P.; Piao, H. R. Eur. J. Med. Chem. 2010, 45, 5739-5743.
http://dx.doi.org/10.1016/j.ejmech.2010.09.031

[10]. Liaras, K.; Geronikaki, A.; Glamoclija, J.; Ciric, A.; Sokovic, M. Bioorg. Med. Chem. 2011, 19, 315-3140.

[11]. Guantai, E. M.; Ncokazi, K.; Egan, T. J.; Gut, J.; Rosenthal, P. J.; Smith, P. J.; Chibale, K. Bioorg. Med. Chem. 2010, 18, 8243-8256.
http://dx.doi.org/10.1016/j.bmc.2010.10.009

[12]. Juvale, K.; Pape, V. F. S.; Wiese, M. Bioorg. Med. Chem. 2012, 20, 346-355.
http://dx.doi.org/10.1016/j.bmc.2011.10.074

[13]. Neves, M. P.; Cravo, S.; Lima, R. T.; Vasconcelos, M. H.; Nascimento, M. S. J.; Silva, A. M. S.; Pinto, M.; Cidade, H.; Correa, A. G. Bioorg. Med. Chem. 2012, 20, 25-33.
http://dx.doi.org/10.1016/j.bmc.2011.11.042

[14]. Srinivasan, B.; Johnson, T. E.; Lad, R.; Xing, C. J. Med. Chem. 2009, 52, 7228-7235.
http://dx.doi.org/10.1021/jm901278z

[15]. Bazzaro, M.; Anchoori, R. K.; Mudiam, M. K. R.; Issaenko, O.; Kumar, S.; Karanam, B.; Lin, Z.; Vogel, R. I.; Gavioli, R.; Destro, F.; Ferretti, V.; Roden, R. B. S.; Khan, S. R. J. Med. Chem. 2011, 54, 449-456
http://dx.doi.org/10.1021/jm100589p

[16]. Kamal, A. Reddy, J. S. Ramaiah, M. J. Dastagiri, D. Bharathi, E. V. Sagar, M. V. P. Pushpavalli, S. N. C. V. L. Ray, P. Bhadra, M. P. Med. Chem. Commun. 2010, 1, 355-360.
http://dx.doi.org/10.1039/c0md00116c

[17]. Biradar, J. S.; Sasidhar, B. S.; Parveen, R. Eur. J. Med. Chem. 2010, 45, 4074-4078
http://dx.doi.org/10.1016/j.ejmech.2010.05.067

[18]. Abuo-Rahma, G. E. A. A.; Abdel-Aziz, M.; Mourad, M. A. E.; Farag, H. H. Bioorg. Med. Chem. 2012, 20, 195-206.
http://dx.doi.org/10.1016/j.bmc.2011.11.012

[19]. Wu, J. Li, J. Cai, Y. Pan, Y. Ye, F. Zhang, Y. Zhao, Y. Yang, S. Li, X. Liang, G. J. Med. Chem. 2011, 54, 8110-8123.
http://dx.doi.org/10.1021/jm200946h

[20]. Chiaradia, L. D.; Martins, P. G. A.; Cordeiro, M. N. S.; Guido, R. V. C.; Ecco, G.; Andricopulo, A. D.; Yunes, R. A.; Vernal, J.; Nunes, R. J.; Hernan, T. J. Med. Chem. 2012, 55, 390-402
http://dx.doi.org/10.1021/jm2012062

[21]. Dsilva, E. D.; Podagatlapalli, G. K.; Rao, S. V.; Rao, D. N.; Dharmaprakash, S. M. Cryst. Growth Design, 2011, 11, 5362-5369.
http://dx.doi.org/10.1021/cg2009539

[22]. Sarojini, B. K.; Narayana, B.; Ashalatha, B. V.; Indira, J.; Lobo, K. G. J. Cryst. Growth. 2006, 295, 54-59.
http://dx.doi.org/10.1016/j.jcrysgro.2006.07.013

[23]. Shettigar, S.; Umesh, G.; Chandrasekharan, K.; Sarojini, B. K.; Narayana, B. Opt. Mater. 2008, 30, 1297-1303
http://dx.doi.org/10.1016/j.optmat.2007.06.008

[24]. Tuncel, S.; Fournier-dit-Chabert, J.; Albrieux, F.; Ahsen, V.; Ducki, S.; Dumoulin, F. Org. Biomol. Chem. 2012, 10, 1154-1157.
http://dx.doi.org/10.1039/c2ob06809e

[25]. Gaber, M. Fayed, T. A. El-Daly, S. A. El-Sayed, Y. S. Photochem. Photobiol. Sci. 2008, 7, 257-262.
http://dx.doi.org/10.1039/b713381b

[26]. Kumar, S.; Bawa, S.; Drabu, S.; Kumar, R.; Gupta, H. Recent Pat. Antiinfect Drug Discov. 2009, 4, 154-63.
http://dx.doi.org/10.2174/157489109789318569

[27]. Kumar, Y.; Green, R.; Wise, D. S.; Wotring, L. L.; Townsend, L. B. J. Med. Chem. 1993, 36, 3849-3852.
http://dx.doi.org/10.1021/jm00076a013

[28]. Ali, M. A.; Siddiqui, A. A.; Shaharyar, M. Eur. J. Med. Chem. 2007, 42, 268-275.
http://dx.doi.org/10.1016/j.ejmech.2006.08.004

[29]. Prasad, Y. R.; Rao, A. L.; Prasoona, L.; Murali, K.; Kumar, P. R. Bioorg. Med. Chem. Lett. 2005, 15, 5030-5034.
http://dx.doi.org/10.1016/j.bmcl.2005.08.040

[30]. Shoman, M. E.; Abdel-Aziz, M.; Aly, O. M.; Farag, H. H.; Morsy, M. A. Eur. J. Med. Chem. 2009, 44, 3068-3852.
http://dx.doi.org/10.1016/j.ejmech.2008.07.008

[31]. Dmytro, H.; Borys, Z.; Olexandr, V.; Lucjusz, Z.; Andrzej, G.; Roman, L.; Eur. J. Med. Chem. 2009, 44, 1396-1404.
http://dx.doi.org/10.1016/j.ejmech.2008.09.032

[32]. Ozdemir, Z.; Kandilici, H. B.; Gumusel, B.; Calis, U.; Bilgin, A. A. Eur. J. Med. Chem. 2007, 42, 373-379.
http://dx.doi.org/10.1016/j.ejmech.2006.09.006

[33]. Wallis, M. P.; Mahmood, N.; William Fraser, W. Il Farmaco 1999, 54, 83-89.
http://dx.doi.org/10.1016/S0014-827X(98)00107-4

[34]. Virsodia, V.; Pissurlenkar, R. R. S.; Manvar, D.; Dholakia, C.; Adlakha, P.; Shah, A.; Coutinho, E. C. Eur. J. Med. Chem. 2008, 43, 2103-2115.
http://dx.doi.org/10.1016/j.ejmech.2007.08.004

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

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

[37]. Asiri, A. M.; Khan, S. A.; Marwani. H. M.; Sharma, K.; J. Photochem. Photobiolo. B: Biology 2013, 120, 82-89.
http://dx.doi.org/10.1016/j.jphotobiol.2013.01.007

[38]. Asiri, A. M.; Khan, S. A. J. Hetrocycl. Chem. 2012, 49, 1434-1438.
http://dx.doi.org/10.1002/jhet.942

[39]. Asiri, A. M.; Khan, S. A. Molecules 2011, 16, 523-531.
http://dx.doi.org/10.3390/molecules16010523

[40]. Asiri, A. M.; Khan, S. A. Molecules 2010, 15(7), 4784-4790.
http://dx.doi.org/10.3390/molecules15074784


How to cite


Khan, S.; Asiri, A.; Kumar, S.; Sharma, K. Eur. J. Chem. 2014, 5(1), 85-90. doi:10.5155/eurjchem.5.1.85-90.789
Khan, S.; Asiri, A.; Kumar, S.; Sharma, K. Green synthesis, antibacterial activity and computational study of pyrazoline and pyrimidine derivatives from 3-(3,4-dimethoxy-phenyl-1-(2,5-dimethyl-thiophen-3-yl)-propenone. Eur. J. Chem. 2014, 5(1), 85-90. doi:10.5155/eurjchem.5.1.85-90.789
Khan, S., Asiri, A., Kumar, S., & Sharma, K. (2014). Green synthesis, antibacterial activity and computational study of pyrazoline and pyrimidine derivatives from 3-(3,4-dimethoxy-phenyl-1-(2,5-dimethyl-thiophen-3-yl)-propenone. European Journal of Chemistry, 5(1), 85-90. doi:10.5155/eurjchem.5.1.85-90.789
Khan, Salman, Abdullah Mohamed Asiri, Sanjay Kumar, & Kamlesh Sharma. "Green synthesis, antibacterial activity and computational study of pyrazoline and pyrimidine derivatives from 3-(3,4-dimethoxy-phenyl-1-(2,5-dimethyl-thiophen-3-yl)-propenone." European Journal of Chemistry [Online], 5.1 (2014): 85-90. Web. 16 Sep. 2019
Khan, Salman, Asiri, Abdullah, Kumar, Sanjay, AND Sharma, Kamlesh. "Green synthesis, antibacterial activity and computational study of pyrazoline and pyrimidine derivatives from 3-(3,4-dimethoxy-phenyl-1-(2,5-dimethyl-thiophen-3-yl)-propenone" European Journal of Chemistry [Online], Volume 5 Number 1 (31 March 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.1.85-90.789

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.