European Journal of Chemistry 2017, 8(1), 96-100 | doi: https://doi.org/10.5155/eurjchem.8.1.96-100.1543 | Get rights and content

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One-pot synthesis and antimicrobial activity of new 4,6-disubstituted-3,4-dihydropyrimidine-2(1H)-thiones


Mahmoud Al-Refai (1,*) , Mohammad Ibrahim (2) , Abdullah Al-Fawwaz (3) , Armin Geyer (4)

(1) Department of Chemistry, Faculty of Science, Al Al-Bayt University, Al-Mafraq, 25113, Jordan
(2) Department of Chemistry, Faculty of Science, Al Al-Bayt University, Al-Mafraq, 25113, Jordan
(3) Department of Biological Sciences, Faculty of Science, Al Al-Bayt University, Al-Mafraq, 25113, Jordan
(4) Faculty of Chemistry, Philipps University Marburg, Hans-Meerwein-Straße 4, Marburg, 35032, Germany
(*) Corresponding Author

Received: 12 Jan 2017 | Revised: 05 Feb 2017 | Accepted: 08 Feb 2017 | Published: 31 Mar 2017 | Issue Date: March 2017

Abstract


A series of 3,4-dihydropyrimidine-2(1H)-thiones (3a-i) were synthesized in moderate yields via a one-pot reaction of 3-acetyl-2,5-diclorothiophene (1), aryl aldehydes (2a-i) and thiourea in methanolic solution of potassium hydroxide under reflux conditions. All newly synthesized compounds were characterized by extensive NMR analysis, including 1D NMR experiments (1H and 13C) and 2D NMR experiments (COSY, HMBC and HSQC), as well as ESI-MS and HRESI-MS data. The antimicrobial activity of all new compounds (3a-f) was tested against bacteria and fungi. Thione derivative (3c) only showed activity against Staphylococcus aureus, Bacillus subtilis and Aspergillus niger.


Keywords


Thione; Thiourea; Pyrimidine; Thiophene; Pyrimidine-2-thione; Antimicrobial activity

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DOI: 10.5155/eurjchem.8.1.96-100.1543

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Funding information


Al Al-Bayt University (Mafraq, Jordan) and the DFG (Germany).

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References


[1]. Eweiss, N. F.; Bahajaj, A. A.; Elsherbini, E. A. J. Heterocycl. Chem. 1986, 23, 1451-1458.
https://doi.org/10.1002/jhet.5570230540

[2]. Hussein, M. A.; El‐Shorbagi, A. N.; Khallil, A. R. Arch. Pharm. 2001, 334, 305-308.
https://doi.org/10.1002/1521-4184(200110)334:10<305::AID-ARDP305>3.0.CO;2-O

[3]. Aboul‐Fadl, T.; Hussein, M. A.; El‐Shorbagi, A. N.; Khallil, A. R. Arch. Pharm. 2002, 335, 438-442.
https://doi.org/10.1002/1521-4184(200212)335:9<438::AID-ARDP438>3.0.CO;2-E

[4]. El-Emam, A. A.; Al-Deeb, O. A.; Al-Omar, M.; Lehmann, J. Bioorg. Med. Chem. 2004, 12, 5107-5113.
https://doi.org/10.1016/j.bmc.2004.07.033

[5]. Kane, J. M.; Dudley, M. W.; Sorensen, S. M.; Miller, F. P. J. Med. Chem. 1988, 31, 1253-1258.
https://doi.org/10.1021/jm00401a031

[6]. Rajesh, S. M.; Kumar, R. S.; Libertsen, L. A.; Perumal, S.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2011, 21, 3012-3016.
https://doi.org/10.1016/j.bmcl.2011.03.045

[7]. Cale, A. D.; Gero, T. W.; Walker, K. R.; Lo, Y. S.; Welstead, W. J.; Jaques, L. W.; Johnson, A. F.; Leonard, C. A.; Nolan, J. C.; Johnson, DN. J. Med. Chem. 1989, 32, 2178-2199.
https://doi.org/10.1021/jm00129a026

[8]. Rao, A.; Carbone, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappala, M. Il Farm. 2002, 57, 747-751.
https://doi.org/10.1016/S0014-827X(02)01268-5

[9]. Krauze, A. A.; Vitolinya, R. O.; Zarin'sh, G. V.; Pelche, Y. E.; Kalme, Z. A.; Kimenis, A. A. Pharm. Chem. J. 1985, 19, 313-318.
https://doi.org/10.1007/BF00766334

[10]. Yarim, M.; Sarac, S.; Ertan, M.; Kilic, F. S.; Erol, K. Arzneimittelforschung 2002, 52, 27-33.

[11]. Wujec, M.; Pitucha, M.; Dobosz, M.; Kosikowska, U.; Malm, A. Acta Pharm. 2004, 54, 251-260.

[12]. Sosnicki, J. G.; Lukasz, S.; Kurzawski, M.; Peruzynska, M.; Maciejewska, G.; Drozdzik, M. Org. Biomol. Chem. 2014, 12, 3427-3440.
https://doi.org/10.1039/c4ob00094c

[13]. Price, D.; May, E. L.; Pickel, F. D. J. Am. Chem. Soc. 1940, 62, 2818-2820.
https://doi.org/10.1021/ja01867a055

[14]. Obermeyer, H. G.; Chen., L. J. Biol. Chem. 1945, 159, 117-122.

[15]. Chen, Q.; Zhu, X. L.; Jiang, L. L.; Liu, Z. M.; Yang, G. F. Eur. J. Med. Chem. 2008, 43, 595-603.
https://doi.org/10.1016/j.ejmech.2007.04.021

[16]. Nugent, R. A.; Schlachter, S. T.; Murphy, M. J.; Cleek, G. J.; Poel, T. J.; Wishka, D. G.; Graber, D. R.; Yagi, Y.; Keiser, B. Y.; Olmsted, R. A.; Kopta, L. A.; Swaney, S. M.; Poppe, S. M.; Morris, J.; Tarpley, W. G.; Thomas, R. C J. Med. Chem. 1998, 41, 3793-3803.
https://doi.org/10.1021/jm9800806

[17]. Hockova, D.; Holy, A.; Masojidkova, M.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Bioorg. Med. Chem. 2004, 12, 3197-3202.
https://doi.org/10.1016/j.bmc.2004.04.002

[18]. Brunelle, M. N.; Lucifora, J.; Neyts, J.; Villet, S.; Holy, A.; Trepo, C.; Zoulim, F. Antimicrob. Agents Chemother. 2007, 51, 2240-2243.
https://doi.org/10.1128/AAC.01440-06

[19]. Costa, E. V.; Pinheiro, M. L. B.; Xavier, C. M.; Silva, J. R.; Amaral, A. C. F.; Souza, A. D.; Barison, A.; Campos, F. R.; Ferreira, A. G.; Machado, G. M.; Leon, L. L. J. Nat. Prod. 2006, 69, 292-294.
https://doi.org/10.1021/np050422s

[20]. Xie, F.; Zhao, H.; Zhao, L.; Lou, L.; Hu, Y. Bioorg. Med. Chem. Lett. 2009, 19, 275-278.
https://doi.org/10.1016/j.bmcl.2008.09.067

[21]. Ghorab, M. M.; Ragab, F. A.; Alqasoumi, S. I.; Alafeefy, A. M.; Aboulmagd, S. A. Eur. J. Med. Chem. 2010, 45, 171-178.
https://doi.org/10.1016/j.ejmech.2009.09.039

[22]. Bachjman, G. B.; Heise, L. V. J. Am. Chem. Soc. 1948, 70, 2368‐2387.

[23]. Al-Refai, M.; Ibrahim, M. M.; Geyer, A.; Marsch, M.; Ali, B. F. J. Chem. Crystallogr. 2016, 46, 331-340.
https://doi.org/10.1007/s10870-016-0661-z

[24]. Alsohaili, S. A.; Al-Fawwaz A. T. Eur. Sci. J. 2014, 10, 156-165.

[25]. Gowri, M.; Ananthalakshmi, S.; Therese Punitha, J. Int. J. of Pharm. Life Sci. 2013, 4, 2780-2784.

[26]. Chenni, M.; El Abed, D.; Rakotomanomana, N.; Fernandez, X.; Chemat, F. Molecules 2016, 21, 113, 1-16.


Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Al-Refai, M.; Ibrahim, M.; Al-Fawwaz, A.; Geyer, A. Eur. J. Chem. 2017, 8(1), 96-100. doi:10.5155/eurjchem.8.1.96-100.1543
Al-Refai, M.; Ibrahim, M.; Al-Fawwaz, A.; Geyer, A. One-pot synthesis and antimicrobial activity of new 4,6-disubstituted-3,4-dihydropyrimidine-2(1H)-thiones. Eur. J. Chem. 2017, 8(1), 96-100. doi:10.5155/eurjchem.8.1.96-100.1543
Al-Refai, M., Ibrahim, M., Al-Fawwaz, A., & Geyer, A. (2017). One-pot synthesis and antimicrobial activity of new 4,6-disubstituted-3,4-dihydropyrimidine-2(1H)-thiones. European Journal of Chemistry, 8(1), 96-100. doi:10.5155/eurjchem.8.1.96-100.1543
Al-Refai, Mahmoud, Mohammad Ibrahim, Abdullah Al-Fawwaz, & Armin Geyer. "One-pot synthesis and antimicrobial activity of new 4,6-disubstituted-3,4-dihydropyrimidine-2(1H)-thiones." European Journal of Chemistry [Online], 8.1 (2017): 96-100. Web. 16 Jun. 2021
Al-Refai, Mahmoud, Ibrahim, Mohammad, Al-Fawwaz, Abdullah, AND Geyer, Armin. "One-pot synthesis and antimicrobial activity of new 4,6-disubstituted-3,4-dihydropyrimidine-2(1H)-thiones" European Journal of Chemistry [Online], Volume 8 Number 1 (31 March 2017)

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