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      Synthesis and biological evaluation of novel fluconazole analogues bearing 1,3,4-oxadiazole moiety as potent antifungal agents

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          Abstract

          A novel series of fluconazole based mimics incorporating 1,3,4-oxadiazole moiety were designed and synthesized. All the title compounds were characterized by (1)H-NMR, (13)C-NMR, and Q-TOF-MS. Preliminary results revealed that most of analogues exhibited significant antifungal activity against seven pathogenic fungi. Compounds 9g and 9k (MIC80 ≤ 0.125 μg/mL, respectively) were found more potent than the positive controls itraconazole and fluconazole as broad-spectrum antifungal agents. The observed docking results showed that the 1,3,4-oxadiazole moiety enhanced the affinity binding to the cytochrome P450 14α-demethylase (CYP51).

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          Most cited references28

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          Amphotericin B: time for a new "gold standard".

          When introduced in 1959, amphotericin B deoxycholate (AmBD) was clearly a life-saving drug. Randomized studies demonstrating its efficacy were not thought to be necessary, and it was granted indications for many invasive fungal infections. Despite its formidable toxicities, AmBD is thus often used as the primary comparator in studies of invasive fungal infections. Safer lipid-based versions of amphotericin B (AmB) have been introduced, but difficulties with studying these agents generally led to licensure for salvage therapy, not primary therapy. However, the cumulative clinical experience to date with the lipid-based preparations is now adequate to demonstrate that these agents are no less active than AmBD, and, for some infections, it can now be stated that specific lipid-based preparations of AmB are superior to AmBD. Given their superior safety profiles, these preparations can now be considered suitable replacements for AmBD for primary therapy for many invasive fungal infections in clinical practice and research.
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            Inhibition of tobacco bacterial wilt with sulfone derivatives containing an 1,3,4-oxadiazole moiety.

            A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by (1)H and (13)C nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 μg/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5'c, 5'h, 5'i, and 5'j could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC(50)) at 39.8, 60.3, 47.9, and 32.1 μg/mL, respectively. Among them, compound 5'j was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)(2)] within the same concentration range. Field trials demonstrated that the control effect of compound 5'j against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.
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              Synthesis of some novel 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents.

              In the present study a series of 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazole derivatives have been synthesized and characterized by IR, 1H NMR, 13C NMR and mass spectral analysis. Synthesized compounds were evaluated for their preliminary cytotoxicity, antimicrobial and antitubercular activity against Mycobacterium tuberculosis H37Rv strain by broth dilution assay method. Antimycobacterial activity tested against M. tuberculosis indicated that compounds 4b and 6g exhibited twofold enhanced potency than parent compound 1 and the results indicate that some of them exhibited promising activities and they deserve more consideration as potential antitubercular agents. Compound 3c, 4b and 6c exhibited good or moderate antibacterial inhibition and compounds 3h and 7c showed excellent antifungal activity. Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.
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                Author and article information

                Journal
                Archives of Pharmacal Research
                Arch. Pharm. Res.
                Springer Nature
                0253-6269
                1976-3786
                April 2015
                May 17 2014
                : 38
                : 4
                : 470-479
                Article
                10.1007/s12272-014-0378-5
                24838380
                2f9c77df-3bb4-4f7f-8462-972c42588f20
                © 2014
                History

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