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Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton
Hatem Moustafa Gaber (1,*)
, Tarek Abdel-Mawgoud Moussa (2) (1) National Organization for Drug Control and Research (NODCAR), Cairo-12553, Egypt
(2) Botany Department, Faculty of Science, Cairo University, Giza 12613, Egypt
(*) Corresponding Author
Received: 01 Jan 2011 | Revised: 15 Mar 2011 | Accepted: 04 Feb 2011 | Published: 30 Jun 2011 | Issue Date: June 2011
Abstract
Versatile 2-(alkylthio)pyrimidine-type and 2-(phenacylamino)thiophene building blocks (4a-d) and 16 were obtained based on an ortho functionalized thiophene derivative 1. A novel series of thieno[2,3-d]pyrimidin-4-one derivatives with annelated bridgehead nitrogen heterocycles was synthesized starting from precursors 4 and 16 through convenient methods. Cyclocondensation of 2-(phenacylthio)pyrimidinone derivative (4b) with sulfuric acid led to the tricyclic thiazole derivative 5. Initial hydrazinolysis of 3-(carbethoxymethyl)pyrimidinone derivative (4d) followed by nitrous acid deamination of the formed N-aminolactam (7) to obtain a N-protodeamino analogue 8a, which on further treatment with formaldehyde and piperidine yielded the respective Mannich-type base 8b. On the other hand, initial hydrazinolysis of 3-unsubstituted pyrimidinone derivative 4a and subsequent acetylation gave the condensed 3-methyltriazole derivative 12, whereas the condensed pyrrole derivative 19 was obtained by heterocyclization of 2-phenacylamine derivative 16 with malononitrile. All newly-obtained thienopyrimidinones with annelated bridgehead nitrogen were screened for their antimicrobial activity against strains of a representative panel of Gram-positive and Gram-negative bacteria as well as fungi together with reference drugs. The compounds under investigation displayed generally good in vitro antibacterial and antifungal activities, with compound 8b that has a N-piperidinylmethyl moiety showing essentially the highest inhibition in both assays. Despite promising antimicrobial activity of N-1-substituted imidazole derivative 8b, the corresponding N-1-unsubstituted analogue 8a displayed poor activity. The heteroannelation of a N-(piperidinylmethyl)imidazole or 3-methyltriazole moiety to the thienopyrimidinone scaffold could be considered as a potential strategy for the development of new therapeutic antimicrobial agents.
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Editor-in-Chief
European Journal of Chemistry
Keywords
Thienopyrimidinone; Alkylation; Cyclodehydration; Hydrazinolysis; Acetylation; Antimicrobial activity
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DOI: 10.5155/eurjchem.2.2.251-259.380
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Citations
[1]. Sergei A. Shipilovskikh, Aleksandr E. Rubtsov
One-Pot Synthesis of Thieno[3,2-e]pyrrolo[1,2-a]pyrimidine Derivative Scaffold: A Valuable Source of PARP-1 Inhibitors
The Journal of Organic Chemistry 84(24), 15788, 2019
DOI: 10.1021/acs.joc.9b00711
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PMid:9342553
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doi:10.1002/jhet.5570270256
[38]. El-Sherief, H. A. H.; El-Naggar, G. M.; Hozien, Z. A.; El-Sawaisi, S. M. J. Heterocycl. Chem. 2008, 45, 467-473.
doi:10.1002/jhet.5570450226
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doi:10.1002/jhet.5570220236
[40]. Pandeya, S. N.; Sriram, D.; Nath, G.; DeClercq, E. Eur. J. Pharm. Sci. 1999, 9, 25-31.
doi:10.1016/S0928-0987(99)00038-X
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doi:10.1016/0223-5234(93)90123-V
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doi:10.1016/0960-894X(95)00558-B
[44]. El Ashry, E. S. H.; El Kilany, Y.; Rashed, N.; Mousaad, A.; Assafir, H. Z. Naturforsch. 1998, 53b, 1203-1212.
[45]. Oganisyan, A. Sh.; Noravyan, A. S.; Karapetyan, A. A.; Aleksanyan, M. S.; Struchkov, Yu. T. Chem. Heterocycl. Compds. 2004, 40, 79-83.
doi:10.1023/B:COHC.0000023772.87295.a9
[46]. Abdel-Fattah, A. M.; Sherif, S. M.; El-Reedy, A. M.; Gad-Alla, S. A. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 70, 67-73.
doi:10.1080/10426509208049153
[47]. Hassaneen, H. M.; Abdelhadi, H. A.; Abdallah, T. A. Tetrahedron 2001, 57, 10133-10138.
doi:10.1016/S0040-4020(01)01026-2
[48]. Reiter, J.; Pongó, L.; Dyortsák, P. Tetrahedron 1987, 43, 2497-2504.
doi:10.1016/S0040-4020(01)81656-2
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[51]. Bakhite, E. A.; Abdel-Rahman, A. E.; Al-Taifi, E. A. J. Chem. Research 2005, 3, 147-154.
doi:10.3184/0308234054213726
[52]. El-Brollosy, N. R.; Abdel-Megeed, M. F.; Genady, A. R. Monatsh. Chem. 2001, 132, 1063-1073.
doi:10.1007/s007060170047
How to cite
Gaber, H.; Moussa, T.
Eur. J. Chem.
2011,
2(2), 251-259.
doi:10.5155/eurjchem.2.2.251-259.380
Gaber, H.; Moussa, T. Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton.
Eur. J. Chem.
2011,
2(2), 251-259.
doi:10.5155/eurjchem.2.2.251-259.380
Gaber, H., & Moussa, T.
(2011).
Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton.
European Journal of Chemistry, 2(2), 251-259.
doi:10.5155/eurjchem.2.2.251-259.380
Gaber, Hatem, & Tarek Abdel-Mawgoud Moussa.
"Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton." European Journal of Chemistry [Online], 2.2 (2011): 251-259. Web. 30 Nov. 2023
Gaber, Hatem, AND Moussa, Tarek.
"Regioselective synthesis and antimicrobial studies of novel bridgehead nitrogen heterocycles containing the thienopyrimidinone skeleton" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)
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DOI Link: https://doi.org/10.5155/eurjchem.2.2.251-259.380
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