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Microwave assisted synthesis and AChE inhibition studies of novel thiazolo and thiadiazolo [3,2-a]pyrimidinone fused dihydrofuran compounds
Novel dihydro-5 H -furo[2,3- d ]thiazolo[3,2- a ]pyrimidin-5-ones ( 3a–r ) and 6 H -furo[2,3- d ][1,3,4]thiadiazolo[3,2- a ]pyrimidin-8(7 H )-ones ( 3s–v ) were designed and obtained from radical cyclizations between 7-hydroxy-5 H -thiazolo[3,2- a ]pyrimidin-5-one derivatives ( 1a–d) and 7-hydroxy-5...
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| Published in: | Medicinal chemistry research 2023-05, Vol.32 (5), p.957-974 |
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| cites | cdi_FETCH-LOGICAL-c319t-9893d2ffca10359ed56d11636ee8f87ee586b3335484e4c4bf3625716d9aede23 |
| container_end_page | 974 |
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| container_start_page | 957 |
| container_title | Medicinal chemistry research |
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| creator | Yilmaz, Mehmet Inal, Aslı Ustalar Sari, Sait |
| description | Novel dihydro-5
H
-furo[2,3-
d
]thiazolo[3,2-
a
]pyrimidin-5-ones (
3a–r
) and 6
H
-furo[2,3-
d
][1,3,4]thiadiazolo[3,2-
a
]pyrimidin-8(7
H
)-ones (
3s–v
) were designed and obtained from radical cyclizations between 7-hydroxy-5
H
-thiazolo[3,2-
a
]pyrimidin-5-one derivatives (
1a–d)
and 7-hydroxy-5
H
-[1,3,4]thiadiazolo[3,2-
a
]pyrimidin-5-one (
1e
) with various alkenes (
2a–h
) mediated by Mn(OAc)
3
. Obtained compounds were characterized with
1
H NMR,
13
C NMR,
19
F NMR, FTIR and HRMS techniques. In vitro AChE inhibitory results of these compounds show that compounds (
3i–p)
are the most active AChEI’s (AChE inhibitor) with IC
50
values between 0.15 and 15.16 µM. Also, ligand protein interactions of two most active compounds (
3i
and
3j
) were investigated by molecular docking studies. Furthermore, druglikeness and ADME analyses of
3i–p
were performed. All tested compounds showed satisfactory druglike characteristics. |
| doi_str_mv | 10.1007/s00044-023-03044-8 |
| format | article |
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H
-furo[2,3-
d
]thiazolo[3,2-
a
]pyrimidin-5-ones (
3a–r
) and 6
H
-furo[2,3-
d
][1,3,4]thiadiazolo[3,2-
a
]pyrimidin-8(7
H
)-ones (
3s–v
) were designed and obtained from radical cyclizations between 7-hydroxy-5
H
-thiazolo[3,2-
a
]pyrimidin-5-one derivatives (
1a–d)
and 7-hydroxy-5
H
-[1,3,4]thiadiazolo[3,2-
a
]pyrimidin-5-one (
1e
) with various alkenes (
2a–h
) mediated by Mn(OAc)
3
. Obtained compounds were characterized with
1
H NMR,
13
C NMR,
19
F NMR, FTIR and HRMS techniques. In vitro AChE inhibitory results of these compounds show that compounds (
3i–p)
are the most active AChEI’s (AChE inhibitor) with IC
50
values between 0.15 and 15.16 µM. Also, ligand protein interactions of two most active compounds (
3i
and
3j
) were investigated by molecular docking studies. Furthermore, druglikeness and ADME analyses of
3i–p
were performed. All tested compounds showed satisfactory druglike characteristics.</description><identifier>ISSN: 1054-2523</identifier><identifier>EISSN: 1554-8120</identifier><identifier>DOI: 10.1007/s00044-023-03044-8</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Acetylcholinesterase ; Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Bioorganic Chemistry ; Inorganic Chemistry ; Medicinal Chemistry ; Molecular docking ; NMR ; Nuclear magnetic resonance ; Original Research ; Pharmacology/Toxicology ; Protein interaction</subject><ispartof>Medicinal chemistry research, 2023-05, Vol.32 (5), p.957-974</ispartof><rights>The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-9893d2ffca10359ed56d11636ee8f87ee586b3335484e4c4bf3625716d9aede23</citedby><cites>FETCH-LOGICAL-c319t-9893d2ffca10359ed56d11636ee8f87ee586b3335484e4c4bf3625716d9aede23</cites><orcidid>0000-0001-7179-4045</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Yilmaz, Mehmet</creatorcontrib><creatorcontrib>Inal, Aslı Ustalar</creatorcontrib><creatorcontrib>Sari, Sait</creatorcontrib><title>Microwave assisted synthesis and AChE inhibition studies of novel thiazolo and thiadiazolo [3,2-a]pyrimidinone fused dihydrofuran compounds</title><title>Medicinal chemistry research</title><addtitle>Med Chem Res</addtitle><description>Novel dihydro-5
H
-furo[2,3-
d
]thiazolo[3,2-
a
]pyrimidin-5-ones (
3a–r
) and 6
H
-furo[2,3-
d
][1,3,4]thiadiazolo[3,2-
a
]pyrimidin-8(7
H
)-ones (
3s–v
) were designed and obtained from radical cyclizations between 7-hydroxy-5
H
-thiazolo[3,2-
a
]pyrimidin-5-one derivatives (
1a–d)
and 7-hydroxy-5
H
-[1,3,4]thiadiazolo[3,2-
a
]pyrimidin-5-one (
1e
) with various alkenes (
2a–h
) mediated by Mn(OAc)
3
. Obtained compounds were characterized with
1
H NMR,
13
C NMR,
19
F NMR, FTIR and HRMS techniques. In vitro AChE inhibitory results of these compounds show that compounds (
3i–p)
are the most active AChEI’s (AChE inhibitor) with IC
50
values between 0.15 and 15.16 µM. Also, ligand protein interactions of two most active compounds (
3i
and
3j
) were investigated by molecular docking studies. Furthermore, druglikeness and ADME analyses of
3i–p
were performed. All tested compounds showed satisfactory druglike characteristics.</description><subject>Acetylcholinesterase</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Bioorganic Chemistry</subject><subject>Inorganic Chemistry</subject><subject>Medicinal Chemistry</subject><subject>Molecular docking</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Original Research</subject><subject>Pharmacology/Toxicology</subject><subject>Protein interaction</subject><issn>1054-2523</issn><issn>1554-8120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kMtKBDEQRRtR8PkDrgJuba28etJLGXyB4kZXIiHTqdiRMRmTbmX8BX_ajCO4c1X3wr1V1KmqQwonFGBymgFAiBoYr4GvlNqodqiURVAGm0VD0Uwyvl3t5vwCwCcg5E71deu7FD_MOxKTs88DWpKXYeixGGKCJWfT_pz40PuZH3wMJA-j9ZhJdCTEd5yToffmM87jT3pl7K9_5MesNk-LZfKv3voQAxI35nLB-n5pU3RjMoF08XURx2DzfrXlzDzjwe_cqx4uzu-nV_XN3eX19Oym7jhth7pVLbfMuc5Q4LJFKxtLacMbROXUBFGqZsY5l0IJFJ2YOd4wOaGNbQ1aZHyvOlrvXaT4NmIe9EscUygnNVMAtFVKiJJi61Thk3NCpxflD5OWmoJeQddr6LpA1z_QtSolvi7lEg7PmP5W_9P6Bm1ah2o</recordid><startdate>20230501</startdate><enddate>20230501</enddate><creator>Yilmaz, Mehmet</creator><creator>Inal, Aslı Ustalar</creator><creator>Sari, Sait</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>FR3</scope><scope>M7Z</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0001-7179-4045</orcidid></search><sort><creationdate>20230501</creationdate><title>Microwave assisted synthesis and AChE inhibition studies of novel thiazolo and thiadiazolo [3,2-a]pyrimidinone fused dihydrofuran compounds</title><author>Yilmaz, Mehmet ; Inal, Aslı Ustalar ; Sari, Sait</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-9893d2ffca10359ed56d11636ee8f87ee586b3335484e4c4bf3625716d9aede23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetylcholinesterase</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Bioorganic Chemistry</topic><topic>Inorganic Chemistry</topic><topic>Medicinal Chemistry</topic><topic>Molecular docking</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Original Research</topic><topic>Pharmacology/Toxicology</topic><topic>Protein interaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yilmaz, Mehmet</creatorcontrib><creatorcontrib>Inal, Aslı Ustalar</creatorcontrib><creatorcontrib>Sari, Sait</creatorcontrib><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 1</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Medicinal chemistry research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yilmaz, Mehmet</au><au>Inal, Aslı Ustalar</au><au>Sari, Sait</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave assisted synthesis and AChE inhibition studies of novel thiazolo and thiadiazolo [3,2-a]pyrimidinone fused dihydrofuran compounds</atitle><jtitle>Medicinal chemistry research</jtitle><stitle>Med Chem Res</stitle><date>2023-05-01</date><risdate>2023</risdate><volume>32</volume><issue>5</issue><spage>957</spage><epage>974</epage><pages>957-974</pages><issn>1054-2523</issn><eissn>1554-8120</eissn><abstract>Novel dihydro-5
H
-furo[2,3-
d
]thiazolo[3,2-
a
]pyrimidin-5-ones (
3a–r
) and 6
H
-furo[2,3-
d
][1,3,4]thiadiazolo[3,2-
a
]pyrimidin-8(7
H
)-ones (
3s–v
) were designed and obtained from radical cyclizations between 7-hydroxy-5
H
-thiazolo[3,2-
a
]pyrimidin-5-one derivatives (
1a–d)
and 7-hydroxy-5
H
-[1,3,4]thiadiazolo[3,2-
a
]pyrimidin-5-one (
1e
) with various alkenes (
2a–h
) mediated by Mn(OAc)
3
. Obtained compounds were characterized with
1
H NMR,
13
C NMR,
19
F NMR, FTIR and HRMS techniques. In vitro AChE inhibitory results of these compounds show that compounds (
3i–p)
are the most active AChEI’s (AChE inhibitor) with IC
50
values between 0.15 and 15.16 µM. Also, ligand protein interactions of two most active compounds (
3i
and
3j
) were investigated by molecular docking studies. Furthermore, druglikeness and ADME analyses of
3i–p
were performed. All tested compounds showed satisfactory druglike characteristics.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s00044-023-03044-8</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0001-7179-4045</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1054-2523 |
| ispartof | Medicinal chemistry research, 2023-05, Vol.32 (5), p.957-974 |
| issn | 1054-2523 1554-8120 |
| language | eng |
| recordid | cdi_proquest_journals_2800198844 |
| source | Springer Nature |
| subjects | Acetylcholinesterase Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Inorganic Chemistry Medicinal Chemistry Molecular docking NMR Nuclear magnetic resonance Original Research Pharmacology/Toxicology Protein interaction |
| title | Microwave assisted synthesis and AChE inhibition studies of novel thiazolo and thiadiazolo [3,2-a]pyrimidinone fused dihydrofuran compounds |
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