Synthesis of Benzofuran‐Based Hybrid Molecules: Molecular Docking and Antibacterial Activity Against Pseudomonas aeruginosa
ABSTRACT A rapid and efficient protocol for synthesizing two series of benzofuran‐based hybrid polyheterocycles is presented: benzofuran‐isatin and benzofuran N‐acylhydrazones, and evaluation of their antibacterial activity both in vitro and in silico against two strains of Pseudomonas aeruginosa, P...
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| Veröffentlicht in: | Journal of heterocyclic chemistry 2024-11, Vol.61 (11), p.1653-1667 |
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| container_title | Journal of heterocyclic chemistry |
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| creator | Cortés‐García, Carlos J. Mercado‐Madrigal, Aidme I. Alejandre‐Castañeda, Viridiana Patiño‐Medina, Jose Alberto Castro‐Velázquez, Verónica Rodríguez‐González, Vicente Ramírez‐Díaz, Martha Isela Islas‐Jácome, Alejandro Rincón‐Guevara, Mónica A. Chacón‐García, Luis Meza‐Carmen, Victor Díaz‐Cervantes, Erik |
| description | ABSTRACT
A rapid and efficient protocol for synthesizing two series of benzofuran‐based hybrid polyheterocycles is presented: benzofuran‐isatin and benzofuran N‐acylhydrazones, and evaluation of their antibacterial activity both in vitro and in silico against two strains of Pseudomonas aeruginosa, PAO1 and PA14 were determined. Six of the tested compounds were shown to be active against the hypervirulent strain PA14. Docking studies were conducted using RNA polymerase sigmaS protein for P. aeruginosa PAO1 and PqsE protein for P. aeruginosa PA14 to provide additional insights into these results. A pharmacophore model was computed to suggest potential structural derivatives on the target molecules, offering further insights for future research. Finally, 40 novel compounds, including intermediates, were synthesized in a three‐step reaction. |
| doi_str_mv | 10.1002/jhet.4887 |
| format | Article |
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A rapid and efficient protocol for synthesizing two series of benzofuran‐based hybrid polyheterocycles is presented: benzofuran‐isatin and benzofuran N‐acylhydrazones, and evaluation of their antibacterial activity both in vitro and in silico against two strains of Pseudomonas aeruginosa, PAO1 and PA14 were determined. Six of the tested compounds were shown to be active against the hypervirulent strain PA14. Docking studies were conducted using RNA polymerase sigmaS protein for P. aeruginosa PAO1 and PqsE protein for P. aeruginosa PA14 to provide additional insights into these results. A pharmacophore model was computed to suggest potential structural derivatives on the target molecules, offering further insights for future research. Finally, 40 novel compounds, including intermediates, were synthesized in a three‐step reaction.</description><identifier>ISSN: 0022-152X</identifier><identifier>EISSN: 1943-5193</identifier><identifier>DOI: 10.1002/jhet.4887</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Inc</publisher><subject>Antiinfectives and antibacterials ; benzofuran ; Chemical synthesis ; docking N‐acylhydrazones ; isatin ; Molecular docking ; molecular hybridization ; Proteins ; Pseudomonas aeruginosa</subject><ispartof>Journal of heterocyclic chemistry, 2024-11, Vol.61 (11), p.1653-1667</ispartof><rights>2024 Wiley Periodicals LLC.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1877-aa5baaac90a2894dc4391646ddfcd59307399cf0de041d83a13298d8e6fe47903</cites><orcidid>0000-0003-2838-7211 ; 0000-0002-1746-3795 ; 0000-0003-4632-6316</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjhet.4887$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjhet.4887$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Cortés‐García, Carlos J.</creatorcontrib><creatorcontrib>Mercado‐Madrigal, Aidme I.</creatorcontrib><creatorcontrib>Alejandre‐Castañeda, Viridiana</creatorcontrib><creatorcontrib>Patiño‐Medina, Jose Alberto</creatorcontrib><creatorcontrib>Castro‐Velázquez, Verónica</creatorcontrib><creatorcontrib>Rodríguez‐González, Vicente</creatorcontrib><creatorcontrib>Ramírez‐Díaz, Martha Isela</creatorcontrib><creatorcontrib>Islas‐Jácome, Alejandro</creatorcontrib><creatorcontrib>Rincón‐Guevara, Mónica A.</creatorcontrib><creatorcontrib>Chacón‐García, Luis</creatorcontrib><creatorcontrib>Meza‐Carmen, Victor</creatorcontrib><creatorcontrib>Díaz‐Cervantes, Erik</creatorcontrib><title>Synthesis of Benzofuran‐Based Hybrid Molecules: Molecular Docking and Antibacterial Activity Against Pseudomonas aeruginosa</title><title>Journal of heterocyclic chemistry</title><description>ABSTRACT
A rapid and efficient protocol for synthesizing two series of benzofuran‐based hybrid polyheterocycles is presented: benzofuran‐isatin and benzofuran N‐acylhydrazones, and evaluation of their antibacterial activity both in vitro and in silico against two strains of Pseudomonas aeruginosa, PAO1 and PA14 were determined. Six of the tested compounds were shown to be active against the hypervirulent strain PA14. Docking studies were conducted using RNA polymerase sigmaS protein for P. aeruginosa PAO1 and PqsE protein for P. aeruginosa PA14 to provide additional insights into these results. A pharmacophore model was computed to suggest potential structural derivatives on the target molecules, offering further insights for future research. Finally, 40 novel compounds, including intermediates, were synthesized in a three‐step reaction.</description><subject>Antiinfectives and antibacterials</subject><subject>benzofuran</subject><subject>Chemical synthesis</subject><subject>docking N‐acylhydrazones</subject><subject>isatin</subject><subject>Molecular docking</subject><subject>molecular hybridization</subject><subject>Proteins</subject><subject>Pseudomonas aeruginosa</subject><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kM9KAzEQh4MoWKsH3yDgycO2yWb_xVut1SoVBSt4W6ZJtk1dk5rsKisIPoLP6JO4tXr0NDP8vpmBD6FDSnqUkLC_XKiqF2VZuoU6lEcsiCln26jTZmFA4_BhF-15v2xHytK0g97vGlMtlNce2wKfKvNmi9qB-fr4PAWvJB43M6clvralEnWp_MlfCw6fWfGozRyDkXhgKj0DUSmnocQDUekXXTV4MAdtfIVvvaqlfbIGPAbl6rk21sM-2img9Orgt3bR_floOhwHk5uLy-FgEgiapWkAEM8AQHACYcYjKSLGaRIlUhZCxpyRlHEuCiIViajMGFAW8kxmKilUlHLCuuhoc3fl7HOtfJUvbe1M-zJnNExiTjOatNTxhhLOeu9Uka-cfgLX5JTka7v52m6-ttuy_Q37qkvV_A_mV-PR9GfjG-cLf68</recordid><startdate>202411</startdate><enddate>202411</enddate><creator>Cortés‐García, Carlos J.</creator><creator>Mercado‐Madrigal, Aidme I.</creator><creator>Alejandre‐Castañeda, Viridiana</creator><creator>Patiño‐Medina, Jose Alberto</creator><creator>Castro‐Velázquez, Verónica</creator><creator>Rodríguez‐González, Vicente</creator><creator>Ramírez‐Díaz, Martha Isela</creator><creator>Islas‐Jácome, Alejandro</creator><creator>Rincón‐Guevara, Mónica A.</creator><creator>Chacón‐García, Luis</creator><creator>Meza‐Carmen, Victor</creator><creator>Díaz‐Cervantes, Erik</creator><general>John Wiley & Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-2838-7211</orcidid><orcidid>https://orcid.org/0000-0002-1746-3795</orcidid><orcidid>https://orcid.org/0000-0003-4632-6316</orcidid></search><sort><creationdate>202411</creationdate><title>Synthesis of Benzofuran‐Based Hybrid Molecules: Molecular Docking and Antibacterial Activity Against Pseudomonas aeruginosa</title><author>Cortés‐García, Carlos J. ; Mercado‐Madrigal, Aidme I. ; Alejandre‐Castañeda, Viridiana ; Patiño‐Medina, Jose Alberto ; Castro‐Velázquez, Verónica ; Rodríguez‐González, Vicente ; Ramírez‐Díaz, Martha Isela ; Islas‐Jácome, Alejandro ; Rincón‐Guevara, Mónica A. ; Chacón‐García, Luis ; Meza‐Carmen, Victor ; Díaz‐Cervantes, Erik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1877-aa5baaac90a2894dc4391646ddfcd59307399cf0de041d83a13298d8e6fe47903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Antiinfectives and antibacterials</topic><topic>benzofuran</topic><topic>Chemical synthesis</topic><topic>docking N‐acylhydrazones</topic><topic>isatin</topic><topic>Molecular docking</topic><topic>molecular hybridization</topic><topic>Proteins</topic><topic>Pseudomonas aeruginosa</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cortés‐García, Carlos J.</creatorcontrib><creatorcontrib>Mercado‐Madrigal, Aidme I.</creatorcontrib><creatorcontrib>Alejandre‐Castañeda, Viridiana</creatorcontrib><creatorcontrib>Patiño‐Medina, Jose Alberto</creatorcontrib><creatorcontrib>Castro‐Velázquez, Verónica</creatorcontrib><creatorcontrib>Rodríguez‐González, Vicente</creatorcontrib><creatorcontrib>Ramírez‐Díaz, Martha Isela</creatorcontrib><creatorcontrib>Islas‐Jácome, Alejandro</creatorcontrib><creatorcontrib>Rincón‐Guevara, Mónica A.</creatorcontrib><creatorcontrib>Chacón‐García, Luis</creatorcontrib><creatorcontrib>Meza‐Carmen, Victor</creatorcontrib><creatorcontrib>Díaz‐Cervantes, Erik</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cortés‐García, Carlos J.</au><au>Mercado‐Madrigal, Aidme I.</au><au>Alejandre‐Castañeda, Viridiana</au><au>Patiño‐Medina, Jose Alberto</au><au>Castro‐Velázquez, Verónica</au><au>Rodríguez‐González, Vicente</au><au>Ramírez‐Díaz, Martha Isela</au><au>Islas‐Jácome, Alejandro</au><au>Rincón‐Guevara, Mónica A.</au><au>Chacón‐García, Luis</au><au>Meza‐Carmen, Victor</au><au>Díaz‐Cervantes, Erik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Benzofuran‐Based Hybrid Molecules: Molecular Docking and Antibacterial Activity Against Pseudomonas aeruginosa</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><date>2024-11</date><risdate>2024</risdate><volume>61</volume><issue>11</issue><spage>1653</spage><epage>1667</epage><pages>1653-1667</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>ABSTRACT
A rapid and efficient protocol for synthesizing two series of benzofuran‐based hybrid polyheterocycles is presented: benzofuran‐isatin and benzofuran N‐acylhydrazones, and evaluation of their antibacterial activity both in vitro and in silico against two strains of Pseudomonas aeruginosa, PAO1 and PA14 were determined. Six of the tested compounds were shown to be active against the hypervirulent strain PA14. Docking studies were conducted using RNA polymerase sigmaS protein for P. aeruginosa PAO1 and PqsE protein for P. aeruginosa PA14 to provide additional insights into these results. A pharmacophore model was computed to suggest potential structural derivatives on the target molecules, offering further insights for future research. Finally, 40 novel compounds, including intermediates, were synthesized in a three‐step reaction.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Inc</pub><doi>10.1002/jhet.4887</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0003-2838-7211</orcidid><orcidid>https://orcid.org/0000-0002-1746-3795</orcidid><orcidid>https://orcid.org/0000-0003-4632-6316</orcidid></addata></record> |
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| subjects | Antiinfectives and antibacterials benzofuran Chemical synthesis docking N‐acylhydrazones isatin Molecular docking molecular hybridization Proteins Pseudomonas aeruginosa |
| title | Synthesis of Benzofuran‐Based Hybrid Molecules: Molecular Docking and Antibacterial Activity Against Pseudomonas aeruginosa |
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