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      Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000–2012

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          Abstract

          This review provides readers with an overview of the main synthetic methodologies for 1,3,4-oxadiazole derivatives, and of their broad spectrum of pharmacological activities as reported over the past twelve years.

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          Oxadiazoles in medicinal chemistry.

          Jonas Boström, Anders Hogner, Antonio Llinàs … (2012)
          Oxadiazoles are five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom, and they exist in different regioisomeric forms. Oxadiazoles are frequently occurring motifs in druglike molecules, and they are often used with the intention of being bioisosteric replacements for ester and amide functionalities. The current study presents a systematic comparison of 1,2,4- and 1,3,4-oxadiazole matched pairs in the AstraZeneca compound collection. In virtually all cases, the 1,3,4-oxadiazole isomer shows an order of magnitude lower lipophilicity (log D), as compared to its isomeric partner. Significant differences are also observed with respect to metabolic stability, hERG inhibition, and aqueous solubility, favoring the 1,3,4-oxadiazole isomers. The difference in profile between the 1,2,4 and 1,3,4 regioisomers can be rationalized by their intrinsically different charge distributions (e.g., dipole moments). To facilitate the use of these heteroaromatic rings, novel synthetic routes for ready access of a broad spectrum of 1,3,4-oxadiazoles, under mild conditions, are described.
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            Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(1-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones.

            A. El-Lakany, Mohamed Omar, Jochen Lehmann … (2004)
            The reaction of 5-(1-adamantyl)-1,3,4-oxadiazoline-2-thione 2 with iodoethane, 2-dimethylaminoethyl chloride hydrochloride or 2-piperidinoethyl chloride hydrochloride in ethanolic potassium hydroxide yielded the corresponding 5-(1-adamantyl)-2-ethyl or substituted ethylthio-1,3,4-oxadiazoles 3a-c. Interaction of 2 with formaldehyde solution and primary aromatic amines or 1-substituted piperazines, in ethanol at room temperature yielded the corresponding 5-(1-adamantyl)-3-arylaminomethyl-1,3,4-oxadiazoline-2-thiones 4a-m or 5-(1-adamantyl)-3-(4-substituted-1-piperazinylmethyl)-1,3,4-oxadiazoline-2-thiones 5a-h, respectively. All the synthesized compounds were tested for in vitro activities against certain strains of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 2, 5a, and 5e were found as the most active derivatives, particularly against the Gram-positive bacteria. In addition, the antiviral activity of compounds 2, 4a-m, and 5a-h against HIV-1 using the XTT assay was carried out. Compound 2 produced 100%, 43%, and 37% reduction of viral replication at 50, 10, and 2microg/mL concentrations, respectively.
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              Synthesis and anticonvulsant activity of new 2-substituted-5- [2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles.

              Ali Almasirad, Sayyed A Tabatabai, Mehrdad Faizi … (2004)
              A series of new 2-substituted-5-[2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles has been synthesized and screened for their anticonvulsant activities. Compound 3 shows considerable anticonvulsant activity both in PTZ and MES models. It seems that this effect is mediated by benzodiazepine receptors and other unknown mechanism, respectively.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 27 August 2012
                Publication date Collection: September 2012
                Volume: 17
                Issue: 9
                Pages: 10192-10231
                Affiliations
                [1 ]Department of Chemistry, Federal University of Paraíba, 58051-900 João Pessoa-PB, Brazil; Email: aldoscarchi@ 123456yahoo.com.br (C.S.O.); brunofrlira@ 123456hotmail.com (B.F.L.)
                [2 ]Laboratory of Pharmaceutical Technology, Federal University of Paraíba, 58051-900 João Pessoa-PB, Brazil; Email: jbarbosa@ 123456ltf.ufpb.br (J.M.B.-F.); jgflorenzo@ 123456hotmail.com (J.G.F.L.)
                Author notes
                [* ] Author to whom correspondence should be addressed; Email: athayde-filho@ 123456quimica.ufpb.br ; Tel.: +55-83-3216-7937.
                Article
                Publisher ID: molecules-17-10192
                DOI: 10.3390/molecules170910192
                PMC ID: 6268307
                PubMed ID: 22926303
                SO-VID: 513332d7-3cca-4081-b297-fa9dea541f84
                Copyright © © 2012 by the authors; licensee MDPI, Basel, Switzerland.
                License:

                This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 23 July 2012
                Date revision received : 15 August 2012
                Date accepted : 17 August 2012
                Categories
                Subject: Review

                Keywords: 1,3,4-oxadiazole,synthesis methods,pharmacological activity,review
                Data availability:
                Keywords: 1,3,4-oxadiazole, synthesis methods, pharmacological activity, review

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