European Journal of Chemistry 2016, 7(3), 298-308. doi:10.5155/eurjchem.7.3.298-308.1447

Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity


Mohamed Ahmed Mahmoud Abdel Reheim (1,*) , Ibrahim Saad Abdel Hafiz (2) , Safaa Mohamed (3)

(1) Department of Chemistry, Faculty of Science, Arish University, Arish 45511, Egypt
(2) Department of Chemistry, Faculty of Science, Arish University, Arish 45511, Egypt
(3) Department of Chemistry, Faculty of Science, Arish University, Arish 45511, Egypt
(*) Corresponding Author

Received: 10 May 2016, Accepted: 11 Jun 2016, Published: 30 Sep 2016

Abstract


A series of many important diverse number of fused heterocyclic systems were prepared from the reaction of 1-(2-hydroxynaphthalen-1-yl)-3-phenylpropane-1,3-dione with some bifunctional nucleophiles, these reactions mainly proceed via condensation of 1-(2-hydroxynaphthalen-1-yl)-3-phenylpropane-1,3-dione with the aldehydic function followed by nucleophilic attack. Structures of the new compounds were established by elemental analyses and spectral data. Some of the products were also screened in vitro for their antimicrobial activity.


Keywords


Pyrazole; Thiophene; β-Diketones; Dihydropyridine; Antimicrobial activity; Tetrahydropyrimidinethione

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DOI: 10.5155/eurjchem.7.3.298-308.1447

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Citations

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[1]. Ilya V Taydakov, Yuliya M Kreshchenova, Ekaterina P Dolotova
A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety
Beilstein Journal of Organic Chemistry  14, 3106, 2018
DOI: 10.3762/bjoc.14.290
/


[2]. Mohamed A. M. Abdel Reheim, Safaa M. Baker
Synthesis, characterization and in vitro antimicrobial activity of novel fused pyrazolo[3,4-c]pyridazine, pyrazolo[3,4-d]pyrimidine, thieno[3,2-c]pyrazole and pyrazolo[3′,4′:4,5]thieno[2,3-d]pyrimidine derivatives
Chemistry Central Journal  11(1), , 2017
DOI: 10.1186/s13065-017-0339-4
/


References

[1]. Alka, C.; Sharma, P. K. Int. J. Chem. Tech. Res. 2011, 3, 11-17.

[2]. Vishnuvardan, R. T.; Lakshmi, P. K.; Jalaja, M.; Jalaja, M. A.; Mohammed, S. B.; Vuday, K. A. Int. J. Res. Pharm. Biomed. Sci. 2011, 2(2), 547-549.

[3]. Sherif, A. F. R. Bioorg. Med. Chem. 2010, 18, 2767-2776.
http://dx.doi.org/10.1016/j.bmc.2010.02.006

[4]. Chauhan, A.; Sharma, P. K.; Kaushik, N. Int. J. Chem. Tech. Res. 2011, 3(1), 11-17.

[5]. Ramaiyan, M.; Ramaiyan, V.; Muthusubramanian, S.; Perumal, Y.; Dharmarajan, S. Bioorg. Med. Chem. Lett. 2010, 20, 6920-6924.
http://dx.doi.org/10.1016/j.bmcl.2010.09.137

[6]. Mistry, B.D.; Desai, K.R.; Patel, J.A.; Patel, N.I. Indian J. Chem. B. 2012, 51, 746-751.

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

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

[9]. Masereel, B.; Wouters, J.; Pochet, L.; Lambert, D. J. Med. Chem. 1998, 41(17), 3239-3244.
http://dx.doi.org/10.1021/jm981022n

[10]. Joachim, S.; Ellen, W.; Rudolf, F. Arzneimittel-Forsch 1963, 13, 200-204.

[11]. Ghoneim, K. M.; Badran, M. M.; Shaaban, M. A.; El-Meligie, S. Egypt J. Pharm. Sci. 1988, 29(1-4), 553-562.

[12]. Ghorab, M. M.; Abdel-Hamide, S. G.; Abou Zeid, M. M. Phosphorus, Sulfur Silicon Rel. Elem. 1996, 112(1-4), 7-17.
http://dx.doi.org/10.1080/10426509608046343

[13]. Baldwin, J. J.; Engelhardt, E. L.; Hirschmann, R.; Penticello, G. S.; Akinson, J. G.; Wasson, B. K.; Sweet, C. S.; Sriabine, A. J. Med. Chem. 1980, 23(1), 65-70.
http://dx.doi.org/10.1021/jm00175a012

[14]. Krauze, A.; Violina, R.; Zarins, G.; Pekers, J.; Kimenis, Z.; Duburs, G. Khim-Farm. Zh 1985, 19, 540-545.

[15]. Van, S.; Eugene, J.; Yu, R. J.; Ger. Offen. 2, 803, 592 (Cl. A61K31 / 455), 02 Aug 1979, Appl. 27 Jan 1978, 23pp. Chem. Abstr., 1980, 92, 47216q.

[16]. Paghdar, D. J.; Akabari, J. D.; Tala, S. D.; Dhaduk, M. F.; Joshi, H. S. Indian J. Heterocycl. Chem 2007, 17, 113-117.

[17]. Mosaad, S. M.; Mohamed, A.; Yasser, M. Z.; Zainab, M. M. Pharmacophore 2012, 3(1), 62-75.

[18]. Baucer, V.; Dalalian, H.; Safir, S. J. Med. Chem. 1968, 11, 1263-1264.
http://dx.doi.org/10.1021/jm00312a610

[19]. El-Agrody, A. M.; Abd El- Latif, M. S.; El-Hady, N. A.; Bedair, A. H. Molecules 2001, 6, 519-527.
http://dx.doi.org/10.3390/60600519

[20]. Bedair, A. H.; Nagwa, A. E.; Abd El-Latif, M. S.; Fakery, A. H.; El-Agrody, A. M. Il Farmaco 2000, 55, 708-714.
http://dx.doi.org/10.1016/S0014-827X(00)00097-5

[21]. El-Agrody, A. M.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H.; El-Sayed, E. M.; El- Ghareab, K. A. Acta Pharm. 2000, 50, 111-120.

[22]. Taylor, R. N.; Cleasby, A.; Singh, O.; Skarzynski, T. J. Med. Chem. 1998, 41, 798-807.
http://dx.doi.org/10.1021/jm9703754

[23]. Hirmoto, K.; Nasuhara, A.; Michiloshi, K.; Kato, T. Kikugawa, K. Mutat. Res. 1997, 395, 47-56.

[24]. Martinez, A. G.; Marco, L. J. Bioorg. Med. Chem. Lett. 1997, 7, 3165-3170.
http://dx.doi.org/10.1016/S0960-894X(97)10165-2

[25]. Dell, C. P.; Smith, C. W. Eur. Pat. 1993, 537, 94, 9, 21 Apr, Chem. Abstr. 1993, 119, 139102d.

[26]. Bianchi, G.; Tava, A. Agr. Bio. Chem. 1987, 51, 2001-2002.

[27]. Eiden, F.; Denk, F. Archiv. Pharm. (Weinheim) 1991, 324, 353-354.
http://dx.doi.org/10.1002/ardp.19913240606

[28]. Shishoo, C. J.; Devani, M. B.; Ullas, G. V.; Ananthan, S.; Bahadit, V. S. J. Hetero. Chem. 1981, 18, 43-46.
http://dx.doi.org/10.1002/jhet.5570180109

[29]. Noda, K.; Nakagawa, A.; Nakajima, Y.; Ide, H.; Japan. Kokai 7785, 194, 15 Jul 1977; Chem. Abstr. 1978, 88, P50908q.

[30]. Joan, F.; Juan-Miguel, J. Bioorg. Med. Chem. Lett. 2001, 11, 2687-2690.
http://dx.doi.org/10.1016/S0960-894X(01)00534-0

[31]. Kunal, N.; Gurinder, D. Bioorg. Med. Chem. 2011, 19, 1950-1958.
http://dx.doi.org/10.1016/j.bmc.2011.01.058

[32]. Stylianakis, A.; Kolocouris, N.; Kolocouris, G.; Fytas, G. B.; Foscolos, E.; Padalko, J.; Neyts, D.; Clerq, E. Bioorg. Med. Chem. Lett. 2003, 13, 1699-1703.
http://dx.doi.org/10.1016/S0960-894X(03)00231-2

[33]. Murray, P. R.; Baron, E. J.; Pfaller, M. A.; Tenover, F. C.; Yolken, R. H.; in: Wood, G. L.; Washington, J. A.; (Eds.). Manual of Clinical Microbiology, Am. Soc. Microbiol., Washington, DC, 1995.

[34]. Jones, R. N.; Barry, A. L.; Gavan, T. L; Washington, I. I. A.; in: Lennette, E. H.; Ballows, A.; Hausler, W. J.; Shadomy, H. J.; (Eds.), Manual of Clinical Microbiology, fourth edn, Am. Soc. Microbiol. 1972, Washington DC 1985.

[35]. Mahmoud, M. M. R.; Ibrahim, S. A.; Mohamed, A. M. A.; Hatem, M. G. J. Chinese Chem. Soc. 2012, 59, 72-80.
http://dx.doi.org/10.1002/jccs.201100194

[36]. Ibrahim, S. A.; Mohamed, A. A.; Mahmoud, M. R. J. Chem. Soc. Pak. 2014, 36(5), 884-889.

[37]. Ibrahim, S. A.; Mohamed, A. M. A.; Safaa, M. B.; Mahmoud, M. R. J. Chem. Soc. Pak. 2014, 36(6), 1133-1144.

[38]. Mohamed, A. M. A.; Ahmed, M. E. T. Int. J. Org. Chem. 2016, 6, 44-54.
http://dx.doi.org/10.4236/ijoc.2016.61005

[39]. Mansouri, M.; Movahedian, A.; Rostami, M.; Fassihi, A. Res. Pharm. Sci. 2012, 7(4), 257-264.

[40]. Mohamed, A. M. A.; Azza, M. E.; Magdy, H. S.; Osama, F. M. Eur. J. Chem. 2012, 3(3), 273-278.
http://dx.doi.org/10.5155/eurjchem.3.3.273-278.605

[41]. Anand, B. P.; Dhaval, G. P.; Saurabh, S. P. J. Appl. Pharm. Sci. 2012, 2(08), 226-232.


How to cite


Reheim, M.; Hafiz, I.; Mohamed, S. Eur. J. Chem. 2016, 7(3), 298-308. doi:10.5155/eurjchem.7.3.298-308.1447
Reheim, M.; Hafiz, I.; Mohamed, S. Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity. Eur. J. Chem. 2016, 7(3), 298-308. doi:10.5155/eurjchem.7.3.298-308.1447
Reheim, M., Hafiz, I., & Mohamed, S. (2016). Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity. European Journal of Chemistry, 7(3), 298-308. doi:10.5155/eurjchem.7.3.298-308.1447
Reheim, Mohamed, Ibrahim Saad Abdel Hafiz, & Safaa Mohamed. "Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity." European Journal of Chemistry [Online], 7.3 (2016): 298-308. Web. 23 Oct. 2019
Reheim, Mohamed, Hafiz, Ibrahim, AND Mohamed, Safaa. "Utility of β-diketones in heterocyclic synthesis: Synthesis of new tetrahydro-pyrimidinethione, pyrazole, thiophene, dihydropyridine, dihydropyrane, pyridazine derivatives and investigation of their antimicrobial activity" European Journal of Chemistry [Online], Volume 7 Number 3 (30 September 2016)

DOI Link: https://doi.org/10.5155/eurjchem.7.3.298-308.1447

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