Synthesis and biological evaluation of a new series of benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides as potential α‐glucosidase inhibitors
A series of new benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides 12a‐n as potential anti‐α‐glucosidase agents were designed and synthesized. α‐Glucosidase inhibition assay demonstrated that all the synthesized compounds 12a‐n (half‐maximal inhibitory concentration [IC50] values in th...
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| Veröffentlicht in: | Journal of biochemical and molecular toxicology 2021-04, Vol.35 (4), p.e22688-n/a |
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| creator | Abedinifar, Fahimeh Mohammadi‐Khanaposhtani, Maryam Asemanipoor, Nafise Mojtabavi, Somayeh Faramarzi, Mohammad A. Mahdavi, Mohammad Biglar, Mahmood Larijani, Bagher Hamedifar, Haleh Hajimiri, Mir H. |
| description | A series of new benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides 12a‐n as potential anti‐α‐glucosidase agents were designed and synthesized. α‐Glucosidase inhibition assay demonstrated that all the synthesized compounds 12a‐n (half‐maximal inhibitory concentration [IC50] values in the range of 40.7 ± 0.3–173.6 ± 1.9 μM) were more potent than standard inhibitor acarbose (IC50 = 750.0 ± 12.5 µM). Among them, the most potent compound was compound 12c, with inhibitory activity around 19‐fold higher than acarbose. Since the most potent compound inhibited α‐glucosidase in a competitive mode, a docking study of this compound was also performed into the active site of α‐glucosidase. In vitro and in silico toxicity assays of the title compounds were also performed. |
| doi_str_mv | 10.1002/jbt.22688 |
| format | Article |
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Among them, the most potent compound was compound 12c, with inhibitory activity around 19‐fold higher than acarbose. Since the most potent compound inhibited α‐glucosidase in a competitive mode, a docking study of this compound was also performed into the active site of α‐glucosidase. In vitro and in silico toxicity assays of the title compounds were also performed.</description><identifier>ISSN: 1095-6670</identifier><identifier>EISSN: 1099-0461</identifier><identifier>DOI: 10.1002/jbt.22688</identifier><identifier>PMID: 33368871</identifier><language>eng</language><publisher>United States: Wiley Subscription Services, Inc</publisher><subject>1,2,3‐triazole ; 1,3,4‐oxadiazole ; Acarbose ; acetamide ; Benzofuran ; Glucosidase ; Oxadiazoles ; Synthesis ; Toxicity ; Triazoles ; α‐glucosidase</subject><ispartof>Journal of biochemical and molecular toxicology, 2021-04, Vol.35 (4), p.e22688-n/a</ispartof><rights>2020 Wiley Periodicals LLC</rights><rights>2020 Wiley Periodicals LLC.</rights><rights>2021 Wiley Periodicals LLC</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3538-4b4dc581b07cd5fc2b7e46c8e34a60cb49b90a3ef8aa0a0fc7854158b93f38033</citedby><cites>FETCH-LOGICAL-c3538-4b4dc581b07cd5fc2b7e46c8e34a60cb49b90a3ef8aa0a0fc7854158b93f38033</cites><orcidid>0000-0002-4171-7310</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjbt.22688$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjbt.22688$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33368871$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abedinifar, Fahimeh</creatorcontrib><creatorcontrib>Mohammadi‐Khanaposhtani, Maryam</creatorcontrib><creatorcontrib>Asemanipoor, Nafise</creatorcontrib><creatorcontrib>Mojtabavi, Somayeh</creatorcontrib><creatorcontrib>Faramarzi, Mohammad A.</creatorcontrib><creatorcontrib>Mahdavi, Mohammad</creatorcontrib><creatorcontrib>Biglar, Mahmood</creatorcontrib><creatorcontrib>Larijani, Bagher</creatorcontrib><creatorcontrib>Hamedifar, Haleh</creatorcontrib><creatorcontrib>Hajimiri, Mir H.</creatorcontrib><title>Synthesis and biological evaluation of a new series of benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides as potential α‐glucosidase inhibitors</title><title>Journal of biochemical and molecular toxicology</title><addtitle>J Biochem Mol Toxicol</addtitle><description>A series of new benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides 12a‐n as potential anti‐α‐glucosidase agents were designed and synthesized. α‐Glucosidase inhibition assay demonstrated that all the synthesized compounds 12a‐n (half‐maximal inhibitory concentration [IC50] values in the range of 40.7 ± 0.3–173.6 ± 1.9 μM) were more potent than standard inhibitor acarbose (IC50 = 750.0 ± 12.5 µM). Among them, the most potent compound was compound 12c, with inhibitory activity around 19‐fold higher than acarbose. Since the most potent compound inhibited α‐glucosidase in a competitive mode, a docking study of this compound was also performed into the active site of α‐glucosidase. In vitro and in silico toxicity assays of the title compounds were also performed.</description><subject>1,2,3‐triazole</subject><subject>1,3,4‐oxadiazole</subject><subject>Acarbose</subject><subject>acetamide</subject><subject>Benzofuran</subject><subject>Glucosidase</subject><subject>Oxadiazoles</subject><subject>Synthesis</subject><subject>Toxicity</subject><subject>Triazoles</subject><subject>α‐glucosidase</subject><issn>1095-6670</issn><issn>1099-0461</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp1kU9u1DAUhyMEoqWw4ALIEhuQJq0d23GyLBV_iip1QVlHz87L1KOMPdgOZbriCByDLRfhEJyknqawQOrqPev36fOTfkXxnNFDRml1tNLpsKrqpnlQ7DPatiUVNXt4u8uyrhXdK57EuKKUylbJx8Ue5zzTiu0XPz9tXbrEaCMB1xNt_eiX1sBI8CuMEyTrHfEDAeLwikQMFuPurdFd-2EK4P58_8EWfCHy9N-gt3DtRyTGuwTWWbckbFEteE5TmLO8gsEEa9tnF0Sy8QldsvnP379yuBwn46PtISKx7tJqm3yIT4tHA4wRn93Ng-Lzu7cXJx_Ks_P3pyfHZ6Xhkjel0KI3smGaKtPLwVRaoahNg1xATY0WrW4pcBwaAAp0MKqRgslGt3zgDeX8oHg1ezfBf5kwpm5to8FxBId-il0lFBdUyWqHvvwPXfkpuHxdV0lWKcplzTL1eqZM8DEGHLpNsGsI247Rbldfl-vrbuvL7Is746TX2P8j__aVgaMZuLIjbu83dR_fXMzKG9ZPrAk</recordid><startdate>202104</startdate><enddate>202104</enddate><creator>Abedinifar, Fahimeh</creator><creator>Mohammadi‐Khanaposhtani, Maryam</creator><creator>Asemanipoor, Nafise</creator><creator>Mojtabavi, Somayeh</creator><creator>Faramarzi, Mohammad A.</creator><creator>Mahdavi, Mohammad</creator><creator>Biglar, Mahmood</creator><creator>Larijani, Bagher</creator><creator>Hamedifar, Haleh</creator><creator>Hajimiri, Mir H.</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>K9.</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-4171-7310</orcidid></search><sort><creationdate>202104</creationdate><title>Synthesis and biological evaluation of a new series of benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides as potential α‐glucosidase inhibitors</title><author>Abedinifar, Fahimeh ; Mohammadi‐Khanaposhtani, Maryam ; Asemanipoor, Nafise ; Mojtabavi, Somayeh ; Faramarzi, Mohammad A. ; Mahdavi, Mohammad ; Biglar, Mahmood ; Larijani, Bagher ; Hamedifar, Haleh ; Hajimiri, Mir H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3538-4b4dc581b07cd5fc2b7e46c8e34a60cb49b90a3ef8aa0a0fc7854158b93f38033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>1,2,3‐triazole</topic><topic>1,3,4‐oxadiazole</topic><topic>Acarbose</topic><topic>acetamide</topic><topic>Benzofuran</topic><topic>Glucosidase</topic><topic>Oxadiazoles</topic><topic>Synthesis</topic><topic>Toxicity</topic><topic>Triazoles</topic><topic>α‐glucosidase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abedinifar, Fahimeh</creatorcontrib><creatorcontrib>Mohammadi‐Khanaposhtani, Maryam</creatorcontrib><creatorcontrib>Asemanipoor, Nafise</creatorcontrib><creatorcontrib>Mojtabavi, Somayeh</creatorcontrib><creatorcontrib>Faramarzi, Mohammad A.</creatorcontrib><creatorcontrib>Mahdavi, Mohammad</creatorcontrib><creatorcontrib>Biglar, Mahmood</creatorcontrib><creatorcontrib>Larijani, Bagher</creatorcontrib><creatorcontrib>Hamedifar, Haleh</creatorcontrib><creatorcontrib>Hajimiri, Mir H.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of biochemical and molecular toxicology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abedinifar, Fahimeh</au><au>Mohammadi‐Khanaposhtani, Maryam</au><au>Asemanipoor, Nafise</au><au>Mojtabavi, Somayeh</au><au>Faramarzi, Mohammad A.</au><au>Mahdavi, Mohammad</au><au>Biglar, Mahmood</au><au>Larijani, Bagher</au><au>Hamedifar, Haleh</au><au>Hajimiri, Mir H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of a new series of benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides as potential α‐glucosidase inhibitors</atitle><jtitle>Journal of biochemical and molecular toxicology</jtitle><addtitle>J Biochem Mol Toxicol</addtitle><date>2021-04</date><risdate>2021</risdate><volume>35</volume><issue>4</issue><spage>e22688</spage><epage>n/a</epage><pages>e22688-n/a</pages><issn>1095-6670</issn><eissn>1099-0461</eissn><abstract>A series of new benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides 12a‐n as potential anti‐α‐glucosidase agents were designed and synthesized. α‐Glucosidase inhibition assay demonstrated that all the synthesized compounds 12a‐n (half‐maximal inhibitory concentration [IC50] values in the range of 40.7 ± 0.3–173.6 ± 1.9 μM) were more potent than standard inhibitor acarbose (IC50 = 750.0 ± 12.5 µM). 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| subjects | 1,2,3‐triazole 1,3,4‐oxadiazole Acarbose acetamide Benzofuran Glucosidase Oxadiazoles Synthesis Toxicity Triazoles α‐glucosidase |
| title | Synthesis and biological evaluation of a new series of benzofuran‐1,3,4‐oxadiazole containing 1,2,3‐triazole‐acetamides as potential α‐glucosidase inhibitors |
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