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Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors
A novel series of phenoxymethybenzoimidazole derivatives ( 9a-n ) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC 50 values in the range of 6.31 to 49.89 μM compared...
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| Published in: | Molecular diversity 2022-08, Vol.26 (4), p.1995-2009 |
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| Main Authors: | , , , , , , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c451t-dc4c75cecef779632536bdf8d150f71fcf6ff28cd23431f6ec1111a08cd7fe533 |
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| cites | cdi_FETCH-LOGICAL-c451t-dc4c75cecef779632536bdf8d150f71fcf6ff28cd23431f6ec1111a08cd7fe533 |
| container_end_page | 2009 |
| container_issue | 4 |
| container_start_page | 1995 |
| container_title | Molecular diversity |
| container_volume | 26 |
| creator | Nasli Esfahani, Anita Iraji, Aida Alamir, Amir Moradi, Shahram Asgari, Mohammad Sadegh Hosseini, Samanesadat Mojtabavi, Somayeh Nasli-Esfahani, Ensieh Faramarzi, Mohammad Ali Bandarian, Fatemeh Larijani, Bagher Hamedifar, Haleh Hajimiri, Mir Hamed Mahdavi, Mohammad |
| description | A novel series of phenoxymethybenzoimidazole derivatives (
9a-n
) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC
50
values in the range of 6.31 to 49.89 μM compared to standard drug acarbose (IC
50
= 750.0 ± 10.0 μM). Enzyme kinetic studies on
9c
,
9g,
and
9m
as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor. |
| doi_str_mv | 10.1007/s11030-021-10310-7 |
| format | article |
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9a-n
) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC
50
values in the range of 6.31 to 49.89 μM compared to standard drug acarbose (IC
50
= 750.0 ± 10.0 μM). Enzyme kinetic studies on
9c
,
9g,
and
9m
as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor.</description><identifier>ISSN: 1381-1991</identifier><identifier>EISSN: 1573-501X</identifier><identifier>DOI: 10.1007/s11030-021-10310-7</identifier><identifier>PMID: 34515954</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Biochemistry ; Biomedical and Life Sciences ; Biotechnology ; Carbohydrates ; Design ; Diabetes ; Endocrinology ; Enzyme kinetics ; Glucose ; Insulin resistance ; Life Sciences ; Metabolism ; Organic Chemistry ; Original ; Original Article ; Pharmaceuticals ; Pharmacy ; Polymer Sciences ; Research centers</subject><ispartof>Molecular diversity, 2022-08, Vol.26 (4), p.1995-2009</ispartof><rights>The Author(s), under exclusive licence to Springer Nature Switzerland AG 2021</rights><rights>The Author(s), under exclusive licence to Springer Nature Switzerland AG 2021.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c451t-dc4c75cecef779632536bdf8d150f71fcf6ff28cd23431f6ec1111a08cd7fe533</citedby><cites>FETCH-LOGICAL-c451t-dc4c75cecef779632536bdf8d150f71fcf6ff28cd23431f6ec1111a08cd7fe533</cites><orcidid>0000-0002-8007-2543</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27922,27923</link.rule.ids></links><search><creatorcontrib>Nasli Esfahani, Anita</creatorcontrib><creatorcontrib>Iraji, Aida</creatorcontrib><creatorcontrib>Alamir, Amir</creatorcontrib><creatorcontrib>Moradi, Shahram</creatorcontrib><creatorcontrib>Asgari, Mohammad Sadegh</creatorcontrib><creatorcontrib>Hosseini, Samanesadat</creatorcontrib><creatorcontrib>Mojtabavi, Somayeh</creatorcontrib><creatorcontrib>Nasli-Esfahani, Ensieh</creatorcontrib><creatorcontrib>Faramarzi, Mohammad Ali</creatorcontrib><creatorcontrib>Bandarian, Fatemeh</creatorcontrib><creatorcontrib>Larijani, Bagher</creatorcontrib><creatorcontrib>Hamedifar, Haleh</creatorcontrib><creatorcontrib>Hajimiri, Mir Hamed</creatorcontrib><creatorcontrib>Mahdavi, Mohammad</creatorcontrib><title>Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors</title><title>Molecular diversity</title><addtitle>Mol Divers</addtitle><description>A novel series of phenoxymethybenzoimidazole derivatives (
9a-n
) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC
50
values in the range of 6.31 to 49.89 μM compared to standard drug acarbose (IC
50
= 750.0 ± 10.0 μM). Enzyme kinetic studies on
9c
,
9g,
and
9m
as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. 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9a-n
) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC
50
values in the range of 6.31 to 49.89 μM compared to standard drug acarbose (IC
50
= 750.0 ± 10.0 μM). Enzyme kinetic studies on
9c
,
9g,
and
9m
as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>34515954</pmid><doi>10.1007/s11030-021-10310-7</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0002-8007-2543</orcidid><oa>free_for_read</oa></addata></record> |
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| issn | 1381-1991 1573-501X |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8436581 |
| source | Springer Nature |
| subjects | Biochemistry Biomedical and Life Sciences Biotechnology Carbohydrates Design Diabetes Endocrinology Enzyme kinetics Glucose Insulin resistance Life Sciences Metabolism Organic Chemistry Original Original Article Pharmaceuticals Pharmacy Polymer Sciences Research centers |
| title | Design and synthesis of phenoxymethybenzoimidazole incorporating different aryl thiazole-triazole acetamide derivatives as α-glycosidase inhibitors |
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