Synthesis of novel mono and bis-indole conduritol derivatives and their α/β-glycosidase inhibitory effects
Here we synthesized four novel indole conduritol derivatives 1–4 for the first time in the literature and probed their biological activities with the α and β-glucosidases. The compounds showed quite effective glucosidase inhibitory action. IC50 values of the compounds were compared with the known gl...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2012-12, Vol.22 (24), p.7499-7503 |
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| container_issue | 24 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Çavdar, Hüseyin Talaz, Oktay Ekinci, Deniz |
| description | Here we synthesized four novel indole conduritol derivatives 1–4 for the first time in the literature and probed their biological activities with the α and β-glucosidases. The compounds showed quite effective glucosidase inhibitory action. IC50 values of the compounds were compared with the known glucosidase inhibitor acarbose and it was determined that newly synthesized indole conduritols had more powerful effect against β-glucosidase in addition to exhibiting moderate influence against α-glucosidase. Our molecules thus constitute an important starting point for the design and exploitation of novel glucosidase inhibitors since glucosidase inhibitors have widespread applications in the treatment of diabetes, viral infections, lysosomal storage diseases and cancers. |
| doi_str_mv | 10.1016/j.bmcl.2012.10.038 |
| format | Article |
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The compounds showed quite effective glucosidase inhibitory action. IC50 values of the compounds were compared with the known glucosidase inhibitor acarbose and it was determined that newly synthesized indole conduritols had more powerful effect against β-glucosidase in addition to exhibiting moderate influence against α-glucosidase. Our molecules thus constitute an important starting point for the design and exploitation of novel glucosidase inhibitors since glucosidase inhibitors have widespread applications in the treatment of diabetes, viral infections, lysosomal storage diseases and cancers.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.10.038</identifier><identifier>PMID: 23137433</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Acarbose ; Biological and medical sciences ; Cancer ; Conduritol ; Diabetes mellitus ; Dose-Response Relationship, Drug ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Glucosidase ; Glycoside Hydrolases - antagonists & inhibitors ; Glycoside Hydrolases - metabolism ; Indole ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; Infection ; Inhibitor ; Inositol - analogs & derivatives ; Inositol - chemical synthesis ; Inositol - pharmacology ; lysosomal storage diseases ; Medical sciences ; Molecular Structure ; Pharmacology. 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The compounds showed quite effective glucosidase inhibitory action. IC50 values of the compounds were compared with the known glucosidase inhibitor acarbose and it was determined that newly synthesized indole conduritols had more powerful effect against β-glucosidase in addition to exhibiting moderate influence against α-glucosidase. Our molecules thus constitute an important starting point for the design and exploitation of novel glucosidase inhibitors since glucosidase inhibitors have widespread applications in the treatment of diabetes, viral infections, lysosomal storage diseases and cancers.</description><subject>Acarbose</subject><subject>Biological and medical sciences</subject><subject>Cancer</subject><subject>Conduritol</subject><subject>Diabetes mellitus</subject><subject>Dose-Response Relationship, Drug</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Glucosidase</subject><subject>Glycoside Hydrolases - antagonists & inhibitors</subject><subject>Glycoside Hydrolases - metabolism</subject><subject>Indole</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Infection</subject><subject>Inhibitor</subject><subject>Inositol - analogs & derivatives</subject><subject>Inositol - chemical synthesis</subject><subject>Inositol - pharmacology</subject><subject>lysosomal storage diseases</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkctqFEEUhgsxmEn0BVxIbQQ3Palb38CNBI1CwEUScFdUV502NVRXxTo9A_NY-iB5JqudUXfi6sDh-w-H_yPkJWdrznhzsVkPkw1rwbgoizWT3ROy4qpRlVSsfkpWrG9Y1fXqyyk5Q9wwxhVT6hk5FZLLVkm5IuFmH-d7QI80jTSmHQQ6pZioiY4OHisfXQpAbYpum_2cAnWQ_c7Mfgf4iypxn-nj94vHH9XXsLcJvTMI1Md7P5RE3lMYR7AzPicnowkIL47znNx9eH97-bG6_nz16fLddWUV7-fKtZJzpurRMsWsq8H0rpcChOO1tIMcpLNgHIOOtVCDGoWyQkhTdw3rrBnkOXlzuPuQ07ct4KwnjxZCMBHSFjUXrWh5z5v6P1DBZCNL3wUVB9TmhJhh1A_ZTybvNWd6EaI3ehGiFyHLrggpoVfH-9thAvcn8ttAAV4fAYPWhDGbaD3-5ZryaqMW7u2Bg1LczkPWaD1EC87n0q12yf_rj5_IYavm</recordid><startdate>20121215</startdate><enddate>20121215</enddate><creator>Çavdar, Hüseyin</creator><creator>Talaz, Oktay</creator><creator>Ekinci, Deniz</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20121215</creationdate><title>Synthesis of novel mono and bis-indole conduritol derivatives and their α/β-glycosidase inhibitory effects</title><author>Çavdar, Hüseyin ; Talaz, Oktay ; Ekinci, Deniz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c419t-d7311045fc040cd5ea9d932e2d153cb3b3dcead0e807e5e4f24c223a58608cab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Acarbose</topic><topic>Biological and medical sciences</topic><topic>Cancer</topic><topic>Conduritol</topic><topic>Diabetes mellitus</topic><topic>Dose-Response Relationship, Drug</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Glucosidase</topic><topic>Glycoside Hydrolases - antagonists & inhibitors</topic><topic>Glycoside Hydrolases - metabolism</topic><topic>Indole</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Infection</topic><topic>Inhibitor</topic><topic>Inositol - analogs & derivatives</topic><topic>Inositol - chemical synthesis</topic><topic>Inositol - pharmacology</topic><topic>lysosomal storage diseases</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. 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The compounds showed quite effective glucosidase inhibitory action. IC50 values of the compounds were compared with the known glucosidase inhibitor acarbose and it was determined that newly synthesized indole conduritols had more powerful effect against β-glucosidase in addition to exhibiting moderate influence against α-glucosidase. Our molecules thus constitute an important starting point for the design and exploitation of novel glucosidase inhibitors since glucosidase inhibitors have widespread applications in the treatment of diabetes, viral infections, lysosomal storage diseases and cancers.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>23137433</pmid><doi>10.1016/j.bmcl.2012.10.038</doi><tpages>5</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2012-12, Vol.22 (24), p.7499-7503 |
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| subjects | Acarbose Biological and medical sciences Cancer Conduritol Diabetes mellitus Dose-Response Relationship, Drug Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Glucosidase Glycoside Hydrolases - antagonists & inhibitors Glycoside Hydrolases - metabolism Indole Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Infection Inhibitor Inositol - analogs & derivatives Inositol - chemical synthesis Inositol - pharmacology lysosomal storage diseases Medical sciences Molecular Structure Pharmacology. Drug treatments Structure-Activity Relationship |
| title | Synthesis of novel mono and bis-indole conduritol derivatives and their α/β-glycosidase inhibitory effects |
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