Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
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 | Issue Date: March 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.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF
DOI: 10.5155/eurjchem.5.1.85-90.789
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 2630 times |
PDF Article downloaded 1141 times
Funding information
Deanship of Scientific Research (DSR) (Grant No. 130-060-D1433), King Abdulaziz University, Jeddah 21589, Saudi Arabia
Citations
[1]. Shrivastava Birendra, Upasna Upasna, Arora Satish Chander
AN ULTRASOUND MEDIATED GREEN SYNTHESIS OF 2-PYRAZOLINE DERIVATIVES
INTERNATIONAL JOURNAL OF SCIENTIFIC RESEARCH , 36, 2021
DOI: 10.36106/ijsr/9527056
[2]. Salman A. Khan, Abdullah Y. Obaid, Laila Mohammad Al-Harb, Muhammad Nadeem Arshad, Abdullah M. Asiri, Michael B. Hursthouse
Synthesis, Spectroscopic, Physicochemical, Crystal Structure and DFT Studies of 4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile Based Azomethine Dyes
International Journal of Electrochemical Science 10(3), 2306, 2015
DOI: 10.1016/S1452-3981(23)04848-4
[3]. Halima Khalid, Sunusi Y. Hussaini, Khatan A. Hasheem, Najib A. Panda
SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF SCHIFF BASE DERIVED FROM GLYCINE AND 4-CHLOROBENZOPHENONE AND ITS METALS COMPLEXES OF Cr(II) and Co(II)
FUDMA JOURNAL OF SCIENCES 6(5), 238, 2022
DOI: 10.33003/fjs-2022-0605-1747
[4]. 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
[5]. Umar Dalha, Aminu Ahmad
Synthesis, Characterization and Anti-Microbial Studies of Metal (II) Complexes of Schiff Base Derived from Condensation of 2-Thiophene Carboxyldehyde and 2-Aminothiophenol
Earthline Journal of Chemical Sciences , 137, 2020
DOI: 10.34198/ejcs.5121.137157
[6]. Mohd Mehkoom, S.M. Afzal, Shabbir Ahmad, Salman A. Khan
The new pyrazoline derivative 5‐(3,4-Dimethoxy‐phenyl)‐3‐(2,5‐dimethyl‐thiophene‐3‐yl),‐4,5‐dihydro‐pyrazole‐1‐carbothioic acid amide (DDPA) as an advisable candidate for optical linearity, nonlinearity, and limiting performance
Journal of Molecular Liquids 345, 117018, 2022
DOI: 10.1016/j.molliq.2021.117018
[7]. 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
[8]. 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
[9]. 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
[10]. Ja’afaru Bello, Habu Nuhu Aliyu, Abdullahi Dangani Hussaini
SYNTHESIS, CHARACTERIZATION, AND IN VITRO ANTIMICROBIAL STUDIES ON NICKEL (II) AND COPPER (II) COMPLEXES OF SCHIFF BASE DERIVED FROM ISATIN (1H-INDOLE-2,3-DIONE) ANDS THIOSEMICARBAZONE
FUDMA JOURNAL OF SCIENCES 7(4), 293, 2023
DOI: 10.33003/fjs-2023-0704-1931
[11]. 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
[12]. Umar Dalha, Aminu Ahmad, Sunusi Yahaya, I.U. Kutama
Characterization of Ni(II) and Cd(II) Metal Complexes using Schiff Base Ligand derived from 2-Thiophenecarboxyldehyde and 2 Aminothiophenol
Earthline Journal of Chemical Sciences , 275, 2021
DOI: 10.34198/ejcs.5221.275294
[13]. Priya Yadav, Manavi Yadav, Rashmi Gaur, Radhika Gupta, Gunjan Arora, Pooja Rana, Anju Srivastava, Rakesh K. Sharma
Fabrication of Copper‐based Silica‐coated Magnetic Nanocatalyst for Efficient One‐pot Synthesis of Chalcones via A3 Coupling of Aldehydes‐Alkynes‐Amines
ChemCatChem 12(9), 2488, 2020
DOI: 10.1002/cctc.202000148
[14]. Christian Schäfer, Hyejin Cho, Bernadett Vlocskó, Guoshu Xie, Béla Török
Recent Advances in the Green Synthesis of Heterocycles: From Building Blocks to Biologically Active Compounds
Current Organic Synthesis 19(3), 426, 2022
DOI: 10.2174/1570179418666210910110205
[15]. R. Bernadett Vlocskó, Guoshu Xie, Béla Török
Green Synthesis of Aromatic Nitrogen-Containing Heterocycles by Catalytic and Non-Traditional Activation Methods
Molecules 28(10), 4153, 2023
DOI: 10.3390/molecules28104153
[16]. 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
[17]. Valkiria Machado, Arthur R. Cenci, Kerolain F. Teixeira, Larissa Sens, Tiago Tizziani, Ricardo J. Nunes, Leonardo L. G. Ferreira, Rosendo A. Yunes, Louis P. Sandjo, Adriano D. Andricopulo, Aldo S. de Oliveira
Pyrazolines as potential anti-Alzheimer's agents: DFT, molecular docking, enzyme inhibition and pharmacokinetic studies
RSC Medicinal Chemistry 13(12), 1644, 2022
DOI: 10.1039/D2MD00262K
[18]. 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
[19]. Mahmoud ABUDAYYAK, Fatma Betül ŞAMLIOĞLU, Beyza SELEN, Seda FANDAKLI, Nurettin YAYLI
Biological Activity of Some Pyrimidine Derivatives: Cytotoxicity and Oxidative Stress Potential in Human Lung Cancer Cell line (A549).
Cumhuriyet Science Journal 41(4), 756, 2020
DOI: 10.17776/csj.758957
[20]. Jayarangarao Prathipati, Paul Douglas Sanasi
One-Pot Green Synthesis of Pyridine-2-carbaldehyde based Chalcones under Solvent-Free Condition using Mesoporous MCM-41 Materials and their Antimicrobial Activities
Asian Journal of Chemistry 34(6), 1498, 2022
DOI: 10.14233/ajchem.2022.23687
[21]. 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
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.5.1.85-90.789
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2014, 5(1), 85-90 | doi: https://doi.org/10.5155/eurjchem.5.1.85-90.789 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • 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 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.