{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,31]],"date-time":"2026-10-31T03:56:56Z","timestamp":1793419016912,"version":"4.5.0"},"reference-count":16,"publisher":"Walter de Gruyter GmbH","issue":"2","license":[{"start":{"date-parts":[[2019,3,28]],"date-time":"2019-03-28T00:00:00Z","timestamp":1553731200000},"content-version":"unspecified","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/3.0"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2019,6,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    In an attempt to produce heterocyclic compounds based on 1,3,4-oxadiazole derivatives with potential antiviral activity, synthesis of compound\n                    <jats:bold>1<\/jats:bold>\n                    [2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)acetonitrile] was performed through the reaction of cyanoacetic acid hydrazide with carbon disulfide in alcoholic potassium hydroxide. Compound\n                    <jats:bold>1<\/jats:bold>\n                    has an activating methylene group, so it was directed toward some specific reactions. Thus, aryldiazonium chlorides reacted with compound\n                    <jats:bold>1<\/jats:bold>\n                    affording hydrazono derivatives\n                    <jats:bold>2a-c<\/jats:bold>\n                    . Also, aromatic aldehydes reacted with compound\n                    <jats:bold>1<\/jats:bold>\n                    to produce compounds\n                    <jats:bold>3a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    . Furthermore, cyclic ketones were subjected to the synthesis of fused thiophene derivatives\n                    <jats:bold>4a,b<\/jats:bold>\n                    <jats:italic>via<\/jats:italic>\n                    reaction with compound\n                    <jats:bold>1<\/jats:bold>\n                    in the presence of elemental sulfur. In addition, 1,3,4-oxadiazole derivative\n                    <jats:bold>1,<\/jats:bold>\n                    when reacted with isothiocyanates, salicylaldehyde or 1,3-dicarbonyl compounds, formed thiazole derivatives\n                    <jats:bold>5a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    , coumarin derivative\n                    <jats:bold>6<\/jats:bold>\n                    and alkenyl derivatives\n                    <jats:bold>7a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    resp. Compound\n                    <jats:bold>7b<\/jats:bold>\n                    underwent cyclization to afford pyridine derivative\n                    <jats:bold>8<\/jats:bold>\n                    . Arylhydrazono derivatives\n                    <jats:bold>9a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    were produced through the reaction of compound\n                    <jats:bold>7a<\/jats:bold>\n                    with aryldiazonium chlorides. Products\n                    <jats:bold>9a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    underwent cyclization to produce pyridazine derivatives\n                    <jats:bold>10a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    . Finally, 1,3,4-oxadiazole derivative\n                    <jats:bold>1<\/jats:bold>\n                    was directed toward reaction with hydrazine derivatives, bromoacetophenone and ethylchloroacetate affording compounds\n                    <jats:bold>11a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    ,\n                    <jats:bold>12<\/jats:bold>\n                    and\n                    <jats:bold>13<\/jats:bold>\n                    , resp. Fused thiophene derivatives\n                    <jats:bold>14a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    were produced\n                    <jats:italic>via<\/jats:italic>\n                    reaction of compounds\n                    <jats:bold>4a<\/jats:bold>\n                    ,\n                    <jats:bold>b<\/jats:bold>\n                    with a mixture of malononitrile and ethylorthoformate. Antiviral activity of the synthesized products showed that 5-(4-amino-3-ethyl-2-thioxo-2,3-dihydrothiazol-5-yl)-1,3,4-oxadiazole-2(3\n                    <jats:italic>H<\/jats:italic>\n                    )-thione (\n                    <jats:bold>5a<\/jats:bold>\n                    ) and 5-(4-amino-3-phenyl-2-thioxo-2,3-dihydrothiazol-5-yl)-1,3,4-oxadiazole-2(3\n                    <jats:italic>H<\/jats:italic>\n                    )-thione (\n                    <jats:bold>5b<\/jats:bold>\n                    ) acted as the most active agents against\n                    <jats:italic>Feline herpes virus, Feline corona virus<\/jats:italic>\n                    ,\n                    <jats:italic>Herpes simplex virus-1<\/jats:italic>\n                    and\n                    <jats:italic>Herpes simplex virus-2<\/jats:italic>\n                    , whereas compound 2-(5-(2-phenylhydrazono)-4,5-dihydro-1,3,4-oxadiazol-2-yl)acetonitrile (\n                    <jats:bold>11b<\/jats:bold>\n                    ) was the most effective against\n                    <jats:italic>Vaccinia virus<\/jats:italic>\n                    ,\n                    <jats:italic>Herpes simplex virus<\/jats:italic>\n                    (TK-KOS-ACVr),\n                    <jats:italic>Coxsackie virus B4<\/jats:italic>\n                    and\n                    <jats:italic>Vesicular stomatitis virus<\/jats:italic>\n                    .\n                  <\/jats:p>","DOI":"10.2478\/acph-2019-0015","type":"journal-article","created":{"date-parts":[[2019,4,1]],"date-time":"2019-04-01T13:30:46Z","timestamp":1554125446000},"page":"261-276","source":"Crossref","is-referenced-by-count":37,"title":["Synthesis and evaluation of some new 1,3,4-oxadiazoles bearing thiophene, thiazole, coumarin, pyridine and pyridazine derivatives as antiviral agents"],"prefix":"10.2478","volume":"69","author":[{"given":"Mohammed","family":"Albratty","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Chemistry , College of Pharmacy Jazan University , P.O. 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