Eco-friendly synthesis of substituted tetrahydroquinolines as potential ecdysone receptor agonists
New eco-friendly approaches were proposed for the synthesis of cis -cyclopentene-annulated heterocyclic compounds containing a tetrahydroquinoline moiety. For the first time we implemented a one-pot three-component cyclocondensation of aromatic amines (aniline, 5-aminoquinoline, o -phenylenediamine)...
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| Veröffentlicht in: | Chemical papers 2023-09, Vol.77 (9), p.5495-5506 |
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| creator | Savchenko, Rimma G. Limantseva, Regina M. Benkovskaya, Galina V. Khairullina, Veronica R. Mozgovoj, Oleg S. |
| description | New eco-friendly approaches were proposed for the synthesis of
cis
-cyclopentene-annulated heterocyclic compounds containing a tetrahydroquinoline moiety. For the first time we implemented a one-pot three-component cyclocondensation of aromatic amines (aniline, 5-aminoquinoline,
o
-phenylenediamine), aldehydes, and cyclopentadiene (CPD) in water and in the ionic liquid. The effect of synthesized substituted 3a,4,5,9b-tetrahydro-3
H
-cyclopenta[
c
]quinolines on the reproduction of house fly imago and on the initial stage of offspring ontogeny was evaluated in comparison with the effect of natural insect hormone using biological screening (
Musca domestica
). The most probable factors of stabilization of prepared compounds
7–10
in the active site of the
Heliothis virescens
receptor were identified using AutoDock 4.2, AutoDock Vina, and GOLD Suite molecular docking software. According to the results of three scoring functions, 4-(3-chlorophenyl)-8-fluoro-3a,4,5,9b-tetrahydro-3
H
-cyclopenta[
c
]quinoline forms the most stable complex with the chosen receptor. The results of bioassays and molecular docking indicate that these compounds may be considered as potential ecdysone agonists. |
| doi_str_mv | 10.1007/s11696-023-02880-7 |
| format | Article |
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cis
-cyclopentene-annulated heterocyclic compounds containing a tetrahydroquinoline moiety. For the first time we implemented a one-pot three-component cyclocondensation of aromatic amines (aniline, 5-aminoquinoline,
o
-phenylenediamine), aldehydes, and cyclopentadiene (CPD) in water and in the ionic liquid. The effect of synthesized substituted 3a,4,5,9b-tetrahydro-3
H
-cyclopenta[
c
]quinolines on the reproduction of house fly imago and on the initial stage of offspring ontogeny was evaluated in comparison with the effect of natural insect hormone using biological screening (
Musca domestica
). The most probable factors of stabilization of prepared compounds
7–10
in the active site of the
Heliothis virescens
receptor were identified using AutoDock 4.2, AutoDock Vina, and GOLD Suite molecular docking software. According to the results of three scoring functions, 4-(3-chlorophenyl)-8-fluoro-3a,4,5,9b-tetrahydro-3
H
-cyclopenta[
c
]quinoline forms the most stable complex with the chosen receptor. The results of bioassays and molecular docking indicate that these compounds may be considered as potential ecdysone agonists.</description><identifier>ISSN: 0366-6352</identifier><identifier>EISSN: 1336-9075</identifier><identifier>EISSN: 2585-7290</identifier><identifier>DOI: 10.1007/s11696-023-02880-7</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Aldehydes ; Amines ; Aminoquinolines ; Aniline ; Biochemistry ; Biotechnology ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Compounds ; Cyclopentene ; Heterocyclic compounds ; Industrial Chemistry/Chemical Engineering ; Insects ; Ionic liquids ; Materials Science ; Medicinal Chemistry ; Molecular docking ; Ontogeny ; Organic compounds ; Original Paper ; Phenylenediamine ; Quinoline ; Receptors ; Substitutes ; Synthesis</subject><ispartof>Chemical papers, 2023-09, Vol.77 (9), p.5495-5506</ispartof><rights>Institute of Chemistry, Slovak Academy of Sciences 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><cites>FETCH-LOGICAL-c270t-d25002adfd61fa71192d8e4c12ae6e8d9fb9b7051b4a5be8ae97df51884a79f63</cites><orcidid>0000-0001-9145-2253</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11696-023-02880-7$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11696-023-02880-7$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27922,27923,41486,42555,51317</link.rule.ids></links><search><creatorcontrib>Savchenko, Rimma G.</creatorcontrib><creatorcontrib>Limantseva, Regina M.</creatorcontrib><creatorcontrib>Benkovskaya, Galina V.</creatorcontrib><creatorcontrib>Khairullina, Veronica R.</creatorcontrib><creatorcontrib>Mozgovoj, Oleg S.</creatorcontrib><title>Eco-friendly synthesis of substituted tetrahydroquinolines as potential ecdysone receptor agonists</title><title>Chemical papers</title><addtitle>Chem. Pap</addtitle><description>New eco-friendly approaches were proposed for the synthesis of
cis
-cyclopentene-annulated heterocyclic compounds containing a tetrahydroquinoline moiety. For the first time we implemented a one-pot three-component cyclocondensation of aromatic amines (aniline, 5-aminoquinoline,
o
-phenylenediamine), aldehydes, and cyclopentadiene (CPD) in water and in the ionic liquid. The effect of synthesized substituted 3a,4,5,9b-tetrahydro-3
H
-cyclopenta[
c
]quinolines on the reproduction of house fly imago and on the initial stage of offspring ontogeny was evaluated in comparison with the effect of natural insect hormone using biological screening (
Musca domestica
). The most probable factors of stabilization of prepared compounds
7–10
in the active site of the
Heliothis virescens
receptor were identified using AutoDock 4.2, AutoDock Vina, and GOLD Suite molecular docking software. According to the results of three scoring functions, 4-(3-chlorophenyl)-8-fluoro-3a,4,5,9b-tetrahydro-3
H
-cyclopenta[
c
]quinoline forms the most stable complex with the chosen receptor. The results of bioassays and molecular docking indicate that these compounds may be considered as potential ecdysone agonists.</description><subject>Aldehydes</subject><subject>Amines</subject><subject>Aminoquinolines</subject><subject>Aniline</subject><subject>Biochemistry</subject><subject>Biotechnology</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Compounds</subject><subject>Cyclopentene</subject><subject>Heterocyclic compounds</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Insects</subject><subject>Ionic liquids</subject><subject>Materials Science</subject><subject>Medicinal Chemistry</subject><subject>Molecular docking</subject><subject>Ontogeny</subject><subject>Organic compounds</subject><subject>Original Paper</subject><subject>Phenylenediamine</subject><subject>Quinoline</subject><subject>Receptors</subject><subject>Substitutes</subject><subject>Synthesis</subject><issn>0366-6352</issn><issn>1336-9075</issn><issn>2585-7290</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kD1PwzAQhi0EEqXwB5gsMQdsJ7bjEVXlQ6rEArPlxOc2VbGLzx3y70kpEhvD6Zb3ee_0EHLL2T1nTD8g58qoiol6mrZllT4jM17XqjJMy3MyY7VSlaqluCRXiFvGmoZJNiPdsk9VyANEvxspjrFsAAekKVA8dFiGcijgaYGS3Wb0OX0dhph2QwSkDuk-FYhlcDsKvR8xRaAZetiXlKlbpzhgwWtyEdwO4eZ3z8nH0_J98VKt3p5fF4-rqhealcoLyZhwPnjFg9OcG-FbaHouHChovQmd6TSTvGuc7KB1YLQPkrdt47QJqp6Tu1Pv_vglYLHbdMhxOmlFK7lpuDRmSolTqs8JMUOw-zx8ujxazuzRpT25tJNL--PS6gmqTxBO4biG_Ff9D_UNiUR6Tw</recordid><startdate>20230901</startdate><enddate>20230901</enddate><creator>Savchenko, Rimma G.</creator><creator>Limantseva, Regina M.</creator><creator>Benkovskaya, Galina V.</creator><creator>Khairullina, Veronica R.</creator><creator>Mozgovoj, Oleg S.</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-9145-2253</orcidid></search><sort><creationdate>20230901</creationdate><title>Eco-friendly synthesis of substituted tetrahydroquinolines as potential ecdysone receptor agonists</title><author>Savchenko, Rimma G. ; Limantseva, Regina M. ; Benkovskaya, Galina V. ; Khairullina, Veronica R. ; Mozgovoj, Oleg S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c270t-d25002adfd61fa71192d8e4c12ae6e8d9fb9b7051b4a5be8ae97df51884a79f63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aldehydes</topic><topic>Amines</topic><topic>Aminoquinolines</topic><topic>Aniline</topic><topic>Biochemistry</topic><topic>Biotechnology</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Compounds</topic><topic>Cyclopentene</topic><topic>Heterocyclic compounds</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Insects</topic><topic>Ionic liquids</topic><topic>Materials Science</topic><topic>Medicinal Chemistry</topic><topic>Molecular docking</topic><topic>Ontogeny</topic><topic>Organic compounds</topic><topic>Original Paper</topic><topic>Phenylenediamine</topic><topic>Quinoline</topic><topic>Receptors</topic><topic>Substitutes</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Savchenko, Rimma G.</creatorcontrib><creatorcontrib>Limantseva, Regina M.</creatorcontrib><creatorcontrib>Benkovskaya, Galina V.</creatorcontrib><creatorcontrib>Khairullina, Veronica R.</creatorcontrib><creatorcontrib>Mozgovoj, Oleg S.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical papers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Savchenko, Rimma G.</au><au>Limantseva, Regina M.</au><au>Benkovskaya, Galina V.</au><au>Khairullina, Veronica R.</au><au>Mozgovoj, Oleg S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Eco-friendly synthesis of substituted tetrahydroquinolines as potential ecdysone receptor agonists</atitle><jtitle>Chemical papers</jtitle><stitle>Chem. Pap</stitle><date>2023-09-01</date><risdate>2023</risdate><volume>77</volume><issue>9</issue><spage>5495</spage><epage>5506</epage><pages>5495-5506</pages><issn>0366-6352</issn><eissn>1336-9075</eissn><eissn>2585-7290</eissn><abstract>New eco-friendly approaches were proposed for the synthesis of
cis
-cyclopentene-annulated heterocyclic compounds containing a tetrahydroquinoline moiety. For the first time we implemented a one-pot three-component cyclocondensation of aromatic amines (aniline, 5-aminoquinoline,
o
-phenylenediamine), aldehydes, and cyclopentadiene (CPD) in water and in the ionic liquid. The effect of synthesized substituted 3a,4,5,9b-tetrahydro-3
H
-cyclopenta[
c
]quinolines on the reproduction of house fly imago and on the initial stage of offspring ontogeny was evaluated in comparison with the effect of natural insect hormone using biological screening (
Musca domestica
). The most probable factors of stabilization of prepared compounds
7–10
in the active site of the
Heliothis virescens
receptor were identified using AutoDock 4.2, AutoDock Vina, and GOLD Suite molecular docking software. According to the results of three scoring functions, 4-(3-chlorophenyl)-8-fluoro-3a,4,5,9b-tetrahydro-3
H
-cyclopenta[
c
]quinoline forms the most stable complex with the chosen receptor. The results of bioassays and molecular docking indicate that these compounds may be considered as potential ecdysone agonists.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><doi>10.1007/s11696-023-02880-7</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0001-9145-2253</orcidid></addata></record> |
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| subjects | Aldehydes Amines Aminoquinolines Aniline Biochemistry Biotechnology Chemistry Chemistry and Materials Science Chemistry/Food Science Compounds Cyclopentene Heterocyclic compounds Industrial Chemistry/Chemical Engineering Insects Ionic liquids Materials Science Medicinal Chemistry Molecular docking Ontogeny Organic compounds Original Paper Phenylenediamine Quinoline Receptors Substitutes Synthesis |
| title | Eco-friendly synthesis of substituted tetrahydroquinolines as potential ecdysone receptor agonists |
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