Abstract
(9-Methyl-5,6-dihydronaphtho[1′,2′:4,5]thieno[2,3-d]pyrimidin-11-yl)hydrazine (1) was used as a precursor for preparation of some novel 1-(9-methyl-5,6-dihydronaphtho[1′,2′:4,5]thieno[2,3-d]pyrimidin-11-yl)-1H-pyrazoles 2–7, -1H-isoindole-1,3(2H)-dione 8, and -pyridazin-3(2H)-one 9. Moreover, the acyclic C-nucleosides 10 and 11 were prepared by treating compound 1 with D-glucose. The in vitro antimicrobial activity of the tested compounds was evaluated by measuring the zone diameters and some of the prepared products showed potent antimicrobial activity in compared with those of well known drugs (standard). In general, the non-acetylated sugar hydrazone derivative 10 showed the highest antibacterial and antifungal potency among the tested compounds and standard with IZ = 22, 21 and 22 mm and MIC = 62.5 and 31.25 μg/ml, respectively.
Highlights
Pyrimidine and fused heterocyclic pyrimidine derivatives have attracted a great deal of interest in particular 4-hydrazinopyrimidine derivatives, which were tested for their medicinal, bactericidal and fungicidal activity [1,2,3,4]
Pyrimidine and heterocyclic annulated pyrimidine derivatives attracted great interest due to the wide variety of interesting biological activities observed for these compounds, such as anticancer [4], antiviral [5], Anti-HIV-1 Activity [6], anti-inflammatory [7] and antimicrobial activities [8]
In view of the above and in continuation of our research program concerned with structural modification of certain biologically active heterocyclic nuclei with the purpose of enhancing their biological activity [10,11,12,13,14,15,16], we aimed to incorporate a fused pyrimidine moiety with other heterocyclic ring system to obtain new functions in an attempt to improve the antimicrobial profile of compounds containing the dihydronaphthothienopyrimidine ring system
Summary
Pyrimidine and fused heterocyclic pyrimidine derivatives have attracted a great deal of interest in particular 4-hydrazinopyrimidine derivatives, which were tested for their medicinal, bactericidal and fungicidal activity [1,2,3,4]. Pyrimidine and heterocyclic annulated pyrimidine derivatives attracted great interest due to the wide variety of interesting biological activities observed for these compounds, such as anticancer [4], antiviral [5], Anti-HIV-1 Activity [6], anti-inflammatory [7] and antimicrobial activities [8]. Several substituted dihydronaphthothienopyrimidine derivatives showed antimicrobial activities against Bacillus subtilis, Escherichia coli, Aspergillus niger and Candida albicans [9], and their ester-containing derivatives demonstrated more antimicrobial activities than the corresponding cyano-containing analogs. In view of the above and in continuation of our research program concerned with structural modification of certain biologically active heterocyclic nuclei with the purpose of enhancing their biological activity [10,11,12,13,14,15,16], we aimed to incorporate a fused pyrimidine moiety with other heterocyclic ring system to obtain new functions in an attempt to improve the antimicrobial profile of compounds containing the dihydronaphthothienopyrimidine ring system
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