Synthesis of non-symmetric N-benzylbispidinol amides and study of their inhibitory activity against the main protease of the SARS-CoV-2 virus
Based on the data obtained by molecular modeling of the non-covalent interaction of non-symmetric N -benzylbispidin-9-ol amides with the active site of the main protease 3CLpro of the SARS-CoV-2 virus, a series of compounds was synthesized, and their inhibitory activity against 3CLpro was studied an...
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| Veröffentlicht in: | Russian chemical bulletin 2023, Vol.72 (1), p.239-247 |
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| creator | Dalinger, A. I. Baev, D. S. Yarovaya, O. I. Chirkova, V. Yu Sharlaeva, E. A. Belenkaya, S. V. Shcherbakov, D. N. Salakhutdinov, N. F. Vatsadze, S. Z. |
| description | Based on the data obtained by molecular modeling of the non-covalent interaction of non-symmetric
N
-benzylbispidin-9-ol amides with the active site of the main protease 3CLpro of the SARS-CoV-2 virus, a series of compounds was synthesized, and their inhibitory activity against 3CLpro was studied and compared with that of the known inhibitor ML188 (IC
50
= 1.56±0.55 µmol L
−1
). It was found that only compound
1g
containing the 1,4-dihydroindeno[1,2-
c
]pyrazole fragment showed moderate activity (IC
50
= 100±5.7µmol L
−1
) and was characterized by the highest calculated binding energy among the studied bispidine derivatives according to molecular docking data. |
| doi_str_mv | 10.1007/s11172-023-3729-x |
| format | Article |
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N
-benzylbispidin-9-ol amides with the active site of the main protease 3CLpro of the SARS-CoV-2 virus, a series of compounds was synthesized, and their inhibitory activity against 3CLpro was studied and compared with that of the known inhibitor ML188 (IC
50
= 1.56±0.55 µmol L
−1
). It was found that only compound
1g
containing the 1,4-dihydroindeno[1,2-
c
]pyrazole fragment showed moderate activity (IC
50
= 100±5.7µmol L
−1
) and was characterized by the highest calculated binding energy among the studied bispidine derivatives according to molecular docking data.</description><identifier>ISSN: 1066-5285</identifier><identifier>EISSN: 1573-9171</identifier><identifier>DOI: 10.1007/s11172-023-3729-x</identifier><identifier>PMID: 36817558</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Amides ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Full ; Full Articles ; Inorganic Chemistry ; Molecular docking ; Organic Chemistry ; Protease ; Pyrazole ; Severe acute respiratory syndrome coronavirus 2 ; Viruses</subject><ispartof>Russian chemical bulletin, 2023, Vol.72 (1), p.239-247</ispartof><rights>Springer Science+Business Media LLC 2023</rights><rights>Springer Science+Business Media LLC 2023.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c400t-fd9e0a7117cf133e27c8a37ad06566e64e269049aee36ed1c3d8c20f2b9661e23</citedby><cites>FETCH-LOGICAL-c400t-fd9e0a7117cf133e27c8a37ad06566e64e269049aee36ed1c3d8c20f2b9661e23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11172-023-3729-x$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11172-023-3729-x$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>230,315,781,785,886,4025,27928,27929,27930,41493,42562,51324</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36817558$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dalinger, A. I.</creatorcontrib><creatorcontrib>Baev, D. S.</creatorcontrib><creatorcontrib>Yarovaya, O. I.</creatorcontrib><creatorcontrib>Chirkova, V. Yu</creatorcontrib><creatorcontrib>Sharlaeva, E. A.</creatorcontrib><creatorcontrib>Belenkaya, S. V.</creatorcontrib><creatorcontrib>Shcherbakov, D. N.</creatorcontrib><creatorcontrib>Salakhutdinov, N. F.</creatorcontrib><creatorcontrib>Vatsadze, S. Z.</creatorcontrib><title>Synthesis of non-symmetric N-benzylbispidinol amides and study of their inhibitory activity against the main protease of the SARS-CoV-2 virus</title><title>Russian chemical bulletin</title><addtitle>Russ Chem Bull</addtitle><addtitle>Russ Chem Bull</addtitle><description>Based on the data obtained by molecular modeling of the non-covalent interaction of non-symmetric
N
-benzylbispidin-9-ol amides with the active site of the main protease 3CLpro of the SARS-CoV-2 virus, a series of compounds was synthesized, and their inhibitory activity against 3CLpro was studied and compared with that of the known inhibitor ML188 (IC
50
= 1.56±0.55 µmol L
−1
). It was found that only compound
1g
containing the 1,4-dihydroindeno[1,2-
c
]pyrazole fragment showed moderate activity (IC
50
= 100±5.7µmol L
−1
) and was characterized by the highest calculated binding energy among the studied bispidine derivatives according to molecular docking data.</description><subject>Amides</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Full</subject><subject>Full Articles</subject><subject>Inorganic Chemistry</subject><subject>Molecular docking</subject><subject>Organic Chemistry</subject><subject>Protease</subject><subject>Pyrazole</subject><subject>Severe acute respiratory syndrome coronavirus 2</subject><subject>Viruses</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kUuLFDEUhQtRnHH0B7iRgBs30TyqkspGGJrxAYOCrW5DOnWrO0NV0iapZsr_4H82RbfjA1zlwP3Oyb2cqnpKyUtKiHyVKKWSYcI45pIpfHuvOqeN5FhRSe8XTYTADWubs-pRSjeEENa27cPqjIuWyqZpz6sf69nnHSSXUOiRDx6neRwhR2fRB7wB_30eNi7tXed8GJAZXQcJGd-hlKduXkzF7iJyfuc2Loc4I2OzO7hcxNY4n_JCoLFItI8hg0lwsqH15ac1XoWvmKGDi1N6XD3ozZDgyem9qL68ufq8eoevP759v7q8xrYmJOO-U0CMLMfbnnIOTNrWcGk6IhohQNTAhCK1MgBcQEct71rLSM82SggKjF9Ur4-5-2kzQmfB52gGvY9uNHHWwTj998S7nd6Gg1aKiZqSEvDiFBDDtwlS1qNLFobBeAhT0kxKxeta1qKgz_9Bb8IUfTlvoYRolJB1oeiRsjGkFKG_W4YSvZStj2XrUrZeyta3xfPszyvuHL_aLQA7AqmM_Bbi76__n_oTIuS4WQ</recordid><startdate>2023</startdate><enddate>2023</enddate><creator>Dalinger, A. I.</creator><creator>Baev, D. S.</creator><creator>Yarovaya, O. I.</creator><creator>Chirkova, V. Yu</creator><creator>Sharlaeva, E. A.</creator><creator>Belenkaya, S. V.</creator><creator>Shcherbakov, D. N.</creator><creator>Salakhutdinov, N. F.</creator><creator>Vatsadze, S. Z.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>2023</creationdate><title>Synthesis of non-symmetric N-benzylbispidinol amides and study of their inhibitory activity against the main protease of the SARS-CoV-2 virus</title><author>Dalinger, A. I. ; Baev, D. S. ; Yarovaya, O. I. ; Chirkova, V. Yu ; Sharlaeva, E. A. ; Belenkaya, S. V. ; Shcherbakov, D. N. ; Salakhutdinov, N. F. ; Vatsadze, S. Z.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c400t-fd9e0a7117cf133e27c8a37ad06566e64e269049aee36ed1c3d8c20f2b9661e23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Amides</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Full</topic><topic>Full Articles</topic><topic>Inorganic Chemistry</topic><topic>Molecular docking</topic><topic>Organic Chemistry</topic><topic>Protease</topic><topic>Pyrazole</topic><topic>Severe acute respiratory syndrome coronavirus 2</topic><topic>Viruses</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dalinger, A. I.</creatorcontrib><creatorcontrib>Baev, D. S.</creatorcontrib><creatorcontrib>Yarovaya, O. I.</creatorcontrib><creatorcontrib>Chirkova, V. Yu</creatorcontrib><creatorcontrib>Sharlaeva, E. A.</creatorcontrib><creatorcontrib>Belenkaya, S. V.</creatorcontrib><creatorcontrib>Shcherbakov, D. N.</creatorcontrib><creatorcontrib>Salakhutdinov, N. F.</creatorcontrib><creatorcontrib>Vatsadze, S. Z.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dalinger, A. I.</au><au>Baev, D. S.</au><au>Yarovaya, O. I.</au><au>Chirkova, V. Yu</au><au>Sharlaeva, E. A.</au><au>Belenkaya, S. V.</au><au>Shcherbakov, D. N.</au><au>Salakhutdinov, N. F.</au><au>Vatsadze, S. Z.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of non-symmetric N-benzylbispidinol amides and study of their inhibitory activity against the main protease of the SARS-CoV-2 virus</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><addtitle>Russ Chem Bull</addtitle><date>2023</date><risdate>2023</risdate><volume>72</volume><issue>1</issue><spage>239</spage><epage>247</epage><pages>239-247</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>Based on the data obtained by molecular modeling of the non-covalent interaction of non-symmetric
N
-benzylbispidin-9-ol amides with the active site of the main protease 3CLpro of the SARS-CoV-2 virus, a series of compounds was synthesized, and their inhibitory activity against 3CLpro was studied and compared with that of the known inhibitor ML188 (IC
50
= 1.56±0.55 µmol L
−1
). It was found that only compound
1g
containing the 1,4-dihydroindeno[1,2-
c
]pyrazole fragment showed moderate activity (IC
50
= 100±5.7µmol L
−1
) and was characterized by the highest calculated binding energy among the studied bispidine derivatives according to molecular docking data.</abstract><cop>New York</cop><pub>Springer US</pub><pmid>36817558</pmid><doi>10.1007/s11172-023-3729-x</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_9926410 |
| source | SpringerNature Journals |
| subjects | Amides Chemistry Chemistry and Materials Science Chemistry/Food Science Full Full Articles Inorganic Chemistry Molecular docking Organic Chemistry Protease Pyrazole Severe acute respiratory syndrome coronavirus 2 Viruses |
| title | Synthesis of non-symmetric N-benzylbispidinol amides and study of their inhibitory activity against the main protease of the SARS-CoV-2 virus |
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