Synthesis and Antibacterial and Antifungal Activity of New Thieno[2,3-d]Pyrimidin-4(3 H )-One Derivatives
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Pharmaceutical Chemistry Journal, Vol. 54, No. 6, September, 2020 (Russian Original Vol. 54, No. 6, June, 2020)
SYNTHESIS AND ANTIBACTERIAL AND ANTIFUNGAL ACTIVITY OF NEW THIENO[2,3-d]PYRIMIDIN-4(3H)-ONE DERIVATIVES B. Kahveci,1 Ý. S. Doðan,2,* E. Menteºe,3 H. E. Sellitepe,2 and D. Kart4 Original article submitted March 30, 2020. A series of new 2-(4/3-substitutedbenzyl)thieno[2,3-d]pyrimidin-4(3H)-ones (2a-f) and 2-(4/3-substituted benzyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one derivatives (3a-f) were synthesized for the first time by the reaction of corresponding 2-aminothiophene-3-carboxamide derivatives and appropriate iminoester hydrochlorides under suitable conditions. Using microdilution method, the antibacterial and antifungal activities of the synthesized compounds were tested against selected strains of Gram positive and Gram negative bacteria (Staphylococcus aureus, Enterecoccus faecalis, Escherichia coli and Pseudomonas aeruginosa) and yeast-like fungi (Candida albicans, C. krusei and C. parapsilosis). In these tests, compounds 3a-f showed higher antifungal activity than fluconazole against Candida fungus species. 2-Substituted thieno[2,3-d]pyrimidin-4(3H)-ones (2a-f) showed better antibacterial activity than 2-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one derivatives (3a-f). Keywords: 2-aminothiophene-3-carboxamide, iminoester hydrochloride, antibacterial activity, antifungal activity.
been synthesized, and their irreversible epidermal growth factor receptor inhibitor activity was observed [9]. Furthermore, tricyclic thienopyrimidines were reported as new inhibitors of Mycobacterium tuberculosis DNA GyrB domain [10, 11]. There were studies showing the effect of these systems on neurodegenerative disorders [12]. Palladium-catalyzed synthesis of these systems was reported [13] and it was established that revealed that such systems were formed via cleavage of the C-C bond of ketoalkyne [14]. In another study, effective method for the synthesis of thienopyrimidines from acid anhydrides or benzoyl chloride was used [15]. Microwave heating has been used for the synthesis of 3H-thieno[2,3-d]pyrimidin-4-ones as alternative to conventional heating [16]. In addition to these studies, there is a growing body of literature that suggests significant biological activity results about this heterocyclic system. In one of these studies, Goudar, et al. synthesized a new series of thienopyrimidine derivatives and evaluated their anti-inflammatory activities. As a result, the thiadiazole-substituted thienopyrimidine derivatives were found to be the most potent [17]. Ouyang, et al. [18] reported some compounds containing this skeleton to be significantly active against breast cancer. In another study [19], a series of new N-(sugar pyranosyl)thienopyrimidine
1. INTRODUCTION The synthesis of new heterocyclic compounds and elucidation of their structures have attracted growing scholarly attention. For this purpose, the pursuit of alternative methods for the synthesis of new
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