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. 2012 Jun 7;17(6):7010-27.
doi: 10.3390/molecules17067010.

5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and new cyclic C-glycoside analogues from carbohydrate precursors with MAO-B, antimicrobial and antifungal activities

Mohamed Mohamed El-Sadek  1 , Seham Yassen Hassan, Nagwa Said Abd El-Dayem, Galila Ahmed Yacout
Affiliations

5-(5-Aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate and new cyclic C-glycoside analogues from carbohydrate precursors with MAO-B, antimicrobial and antifungal activities

Mohamed Mohamed El-Sadek et al. Molecules. .

Abstract

Cyclization of acyclic C-glycoside derivatives 1a,b to 2a,b as the major isomers, and 4a,b as the minor isomers were carried out. The isopropylidene derivatives 3a,b were prepared, as well as the hydrazide derivative 6, which was condensed with a variety of aldehydes to give hydrazones 7a-e which were also prepared from the compounds 12a-e. Acetylation of 7a,d gave the corresponding acetyl derivatives 8a,d, respectively. In addition, the dicarbonyl compound 9 was prepared in the hydrate form, which reacted with a number of aroylhydrazines to give the corresponding bisaroylhydrazones 10a-d, which were cyclized into 1,3,4-oxadiazoles 11a-d. Furthermore, two of the prepared compounds were examined to show the ability to activate MAO-B. In addition a number of prepared compounds showed antibacterial and antiviral activities.

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Figures

Scheme 1
Scheme 1
Synthesis of isopropylidene derivatives 3a,b.
Figure 1
Figure 1
2D 1H-NMR spectrum of compound 3b.
Scheme 2
Scheme 2
Synthesis of carbohydrazone derivatives.
Scheme 3
Scheme 3
Synthesis of bisaroylhydrazone derivatives 10a–d.
Scheme 4
Scheme 4
Synthesis of 1,3,4-oxadiazole derivatives 11a–d.
Scheme 5
Scheme 5
Proposed mechanism for formation of ethyl 2-methyl-5-(5-aryl-1,3,4-oxadiazole-2-carbonyl)furan-3-carboxylate.
Figure 2
Figure 2
Effect of substrate concentration on the rate of MAO-B catalyzed reactions in the presence of the examined compounds 7c,e compared to control.
See this image and copyright information in PMC

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References

    1. Rainier J.D., Cox J.M. Aluminum- and boron-mediated C-glycoside synthesis from 1,2-anhydro-glycosides. Org. Lett. 2000;2:2707–2709. doi: 10.1021/ol006286u. - DOI - PubMed
    1. Yale H.L., Losee K. 2-Amino-5-substituted 1,3,4-oxadiazoles and 5-imino-2-substituted Δ2-1,3,4-oxadiazolines. A group of novel muscle relaxants. J. Med. Chem. 1966;9:478–483. doi: 10.1021/jm00322a007. - DOI - PubMed
    1. Omar F.A., Mahfouz N.M., Rahman M.A. Design, synthesis and anti-inflammatory activity of some 1,3,4-oxadiazole derivatives. Eur. J. Med. Chem. 1996;31:819–825. doi: 10.1016/0223-5234(96)83976-6. - DOI - PubMed
    1. Palusa S.K.G., Udupi R.H., Himabindu V., Sridhara A.M. Synthesis and evaluation of a series of pyrimidine substituted 1,3,4-oxadiazole derivatives as antimicrobial and anti-inflammatory agents. Org. Commun. 2011;4:82–93.
    1. Tan T.M.C., Chen Y., Kong K.H., Bai J., Li Y., Lim S.G., Ang T.H., Lam Y. Synthesis and the biological evaluation of 2-benzenesulfonyl alkyl-5-substituted-sulfanyl-(1,3,4)-oxadiazoles as potential anti-hepatitis B virus agents. Antiviral Res. 2006;71:7–14. doi: 10.1016/j.antiviral.2006.02.007. - DOI - PubMed

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