Synthesis, antioxidant, and molecular docking of new fluorescent (4‐alkoxyphenyl)‐nitrothiophene compounds
New fluorescent 4‐alkoxyphenyl‐nitrothiophene compounds 4a–d bearing diverse alkoxyl tails are described. The synthetic strategy was simply accomplished by alkali‐assisted alkylation of 4‐(5‐nitrothiophen‐2‐yl)phenol (3) with propyl, hexyl, nonyl, and/or dodecyl iodide. The molecular structures were...
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| Veröffentlicht in: | Luminescence (Chichester, England) England), 2023-08, Vol.38 (8), p.1493-1500 |
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| creator | Miled, Wafa Abomuti, May Abdullah Alotaibi, Fatimah A. Alhadhrami, Nahlah A. Zghab, Imen |
| description | New fluorescent 4‐alkoxyphenyl‐nitrothiophene compounds 4a–d bearing diverse alkoxyl tails are described. The synthetic strategy was simply accomplished by alkali‐assisted alkylation of 4‐(5‐nitrothiophen‐2‐yl)phenol (3) with propyl, hexyl, nonyl, and/or dodecyl iodide. The molecular structures were determined using infrared (IR), 1H NMR, and mass spectroscopy. Ultraviolet–visible (UV–vis) absorption and emission spectra of the produced 4‐alkoxyphenyl‐nitrothiophenes revealed considerable extinction coefficients, which were shown to be controlled by the thiophene bridge in conjugation with the alkoxy donor moiety. It was found that the maximum absorbance wavelength was affected by the alkoxyl group‐bonded substituents. The antioxidant efficiency obtained from the 4‐alkoxyphenyl‐nitrothiophene hybrids was excellent compared with that widely used drugs [butylated hydroxytoluene (BHT) and vitamin C]. Unlike 2‐(4‐[dodecyloxy]phenyl)‐5‐nitrothiophene hybrid 4d, which has made solid claims about the good effect of its reference drugs and vitamins, Docking investigations of the prepared 4‐alkoxyphenyl‐nitrothiophene hybrids towards the selected 5IKQ protein revealed impressive coordination and antioxidant effectiveness.
2‐(4‐[Hexyloxy]phenyl)‐5‐nitrothiophene hybrid 4b displayed a fluorescence colour in dimethyl sulphoxide (DMSO) in UV spectra, better radical scavenging, and a rational docking score with S = −7.2694 kcal/mol and RMSD = 0.8550 in s molecular docking study towards PDB: 5IKQ. |
| doi_str_mv | 10.1002/bio.4531 |
| format | Article |
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2‐(4‐[Hexyloxy]phenyl)‐5‐nitrothiophene hybrid 4b displayed a fluorescence colour in dimethyl sulphoxide (DMSO) in UV spectra, better radical scavenging, and a rational docking score with S = −7.2694 kcal/mol and RMSD = 0.8550 in s molecular docking study towards PDB: 5IKQ.</description><identifier>ISSN: 1522-7235</identifier><identifier>EISSN: 1522-7243</identifier><identifier>DOI: 10.1002/bio.4531</identifier><identifier>PMID: 37259924</identifier><language>eng</language><publisher>England: Wiley Subscription Services, Inc</publisher><subject>(4‐alkoxyphenyl)‐nitrothiophene ; 4‐(5‐nitrothiophen‐2‐yl)phenol ; Alkylation ; Analytical methods ; antioxidant ; Antioxidants ; Antioxidants - chemistry ; Ascorbic Acid ; Bridges ; Butylated hydroxytoluene ; Chemical Phenomena ; Chemical synthesis ; Coefficients ; Coloring Agents ; Conjugation ; Drugs ; Emission spectra ; Fluorescence ; hexyl iodide ; Hybrids ; Iodides ; Mass spectroscopy ; Molecular docking ; Molecular Docking Simulation ; Molecular Structure ; NMR ; Nuclear magnetic resonance ; Phenols ; pull–push ; Vitamins ; Wavelength</subject><ispartof>Luminescence (Chichester, England), 2023-08, Vol.38 (8), p.1493-1500</ispartof><rights>2023 John Wiley & Sons Ltd.</rights><rights>2023 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3491-2033d8b0214800453959037dd55ee1dbfbb4ea07a77f6cedd9adde01db3d5f193</citedby><cites>FETCH-LOGICAL-c3491-2033d8b0214800453959037dd55ee1dbfbb4ea07a77f6cedd9adde01db3d5f193</cites><orcidid>0000-0003-1805-5926</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%2Fbio.4531$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fbio.4531$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37259924$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Miled, Wafa</creatorcontrib><creatorcontrib>Abomuti, May Abdullah</creatorcontrib><creatorcontrib>Alotaibi, Fatimah A.</creatorcontrib><creatorcontrib>Alhadhrami, Nahlah A.</creatorcontrib><creatorcontrib>Zghab, Imen</creatorcontrib><title>Synthesis, antioxidant, and molecular docking of new fluorescent (4‐alkoxyphenyl)‐nitrothiophene compounds</title><title>Luminescence (Chichester, England)</title><addtitle>Luminescence</addtitle><description>New fluorescent 4‐alkoxyphenyl‐nitrothiophene compounds 4a–d bearing diverse alkoxyl tails are described. The synthetic strategy was simply accomplished by alkali‐assisted alkylation of 4‐(5‐nitrothiophen‐2‐yl)phenol (3) with propyl, hexyl, nonyl, and/or dodecyl iodide. The molecular structures were determined using infrared (IR), 1H NMR, and mass spectroscopy. Ultraviolet–visible (UV–vis) absorption and emission spectra of the produced 4‐alkoxyphenyl‐nitrothiophenes revealed considerable extinction coefficients, which were shown to be controlled by the thiophene bridge in conjugation with the alkoxy donor moiety. It was found that the maximum absorbance wavelength was affected by the alkoxyl group‐bonded substituents. The antioxidant efficiency obtained from the 4‐alkoxyphenyl‐nitrothiophene hybrids was excellent compared with that widely used drugs [butylated hydroxytoluene (BHT) and vitamin C]. Unlike 2‐(4‐[dodecyloxy]phenyl)‐5‐nitrothiophene hybrid 4d, which has made solid claims about the good effect of its reference drugs and vitamins, Docking investigations of the prepared 4‐alkoxyphenyl‐nitrothiophene hybrids towards the selected 5IKQ protein revealed impressive coordination and antioxidant effectiveness.
2‐(4‐[Hexyloxy]phenyl)‐5‐nitrothiophene hybrid 4b displayed a fluorescence colour in dimethyl sulphoxide (DMSO) in UV spectra, better radical scavenging, and a rational docking score with S = −7.2694 kcal/mol and RMSD = 0.8550 in s molecular docking study towards PDB: 5IKQ.</description><subject>(4‐alkoxyphenyl)‐nitrothiophene</subject><subject>4‐(5‐nitrothiophen‐2‐yl)phenol</subject><subject>Alkylation</subject><subject>Analytical methods</subject><subject>antioxidant</subject><subject>Antioxidants</subject><subject>Antioxidants - chemistry</subject><subject>Ascorbic Acid</subject><subject>Bridges</subject><subject>Butylated hydroxytoluene</subject><subject>Chemical Phenomena</subject><subject>Chemical synthesis</subject><subject>Coefficients</subject><subject>Coloring Agents</subject><subject>Conjugation</subject><subject>Drugs</subject><subject>Emission spectra</subject><subject>Fluorescence</subject><subject>hexyl iodide</subject><subject>Hybrids</subject><subject>Iodides</subject><subject>Mass spectroscopy</subject><subject>Molecular docking</subject><subject>Molecular Docking Simulation</subject><subject>Molecular Structure</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Phenols</subject><subject>pull–push</subject><subject>Vitamins</subject><subject>Wavelength</subject><issn>1522-7235</issn><issn>1522-7243</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kctOwzAQRS0E4lGQ-AIUiU2RSPErSbMExEtCYgGsIyeeUINjFztRmx2fwDfyJbi0dIHEamY8R1d3fBE6JHhEMKZnpbIjnjCygXZJQmmcUc421z1LdtCe968Y4zRN8220wzKa5Dnlu8g89qadgFf-NBKmVXauZKiLQUaN1VB1WrhI2upNmZfI1pGBWVTrzjrwFZg2GvKvj0-h3-y8n07A9PokzEa1zrYTZRdPEFW2mdrOSL-PtmqhPRys6gA9X189Xd7G9w83d5fn93HFeE5iihmT4xJTwscYh8vyJMcskzJJAIgs67LkIHAmsqxOK5AyF1ICDhsmk5rkbICGS92ps-8d-LZoVLCrtTBgO1_QMSUpZ2mWBfT4D_pqO2eCu0Bxziklwc5asHLWewd1MXWqEa4vCC4WGRQhg2KRQUCPVoJd2YBcg7-fHoB4CcyUhv5foeLi7uFH8Bu9ZpMh</recordid><startdate>202308</startdate><enddate>202308</enddate><creator>Miled, Wafa</creator><creator>Abomuti, May Abdullah</creator><creator>Alotaibi, Fatimah A.</creator><creator>Alhadhrami, Nahlah A.</creator><creator>Zghab, Imen</creator><general>Wiley Subscription Services, Inc</general><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>7QF</scope><scope>7QO</scope><scope>7QP</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7U5</scope><scope>7U7</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H95</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L.G</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-1805-5926</orcidid></search><sort><creationdate>202308</creationdate><title>Synthesis, antioxidant, and molecular docking of new fluorescent (4‐alkoxyphenyl)‐nitrothiophene compounds</title><author>Miled, Wafa ; Abomuti, May Abdullah ; Alotaibi, Fatimah A. ; Alhadhrami, Nahlah A. ; Zghab, Imen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3491-2033d8b0214800453959037dd55ee1dbfbb4ea07a77f6cedd9adde01db3d5f193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>(4‐alkoxyphenyl)‐nitrothiophene</topic><topic>4‐(5‐nitrothiophen‐2‐yl)phenol</topic><topic>Alkylation</topic><topic>Analytical methods</topic><topic>antioxidant</topic><topic>Antioxidants</topic><topic>Antioxidants - chemistry</topic><topic>Ascorbic Acid</topic><topic>Bridges</topic><topic>Butylated hydroxytoluene</topic><topic>Chemical Phenomena</topic><topic>Chemical synthesis</topic><topic>Coefficients</topic><topic>Coloring Agents</topic><topic>Conjugation</topic><topic>Drugs</topic><topic>Emission spectra</topic><topic>Fluorescence</topic><topic>hexyl iodide</topic><topic>Hybrids</topic><topic>Iodides</topic><topic>Mass spectroscopy</topic><topic>Molecular docking</topic><topic>Molecular Docking Simulation</topic><topic>Molecular Structure</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Phenols</topic><topic>pull–push</topic><topic>Vitamins</topic><topic>Wavelength</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Miled, Wafa</creatorcontrib><creatorcontrib>Abomuti, May Abdullah</creatorcontrib><creatorcontrib>Alotaibi, Fatimah A.</creatorcontrib><creatorcontrib>Alhadhrami, Nahlah A.</creatorcontrib><creatorcontrib>Zghab, Imen</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Luminescence (Chichester, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Miled, Wafa</au><au>Abomuti, May Abdullah</au><au>Alotaibi, Fatimah A.</au><au>Alhadhrami, Nahlah A.</au><au>Zghab, Imen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, antioxidant, and molecular docking of new fluorescent (4‐alkoxyphenyl)‐nitrothiophene compounds</atitle><jtitle>Luminescence (Chichester, England)</jtitle><addtitle>Luminescence</addtitle><date>2023-08</date><risdate>2023</risdate><volume>38</volume><issue>8</issue><spage>1493</spage><epage>1500</epage><pages>1493-1500</pages><issn>1522-7235</issn><eissn>1522-7243</eissn><abstract>New fluorescent 4‐alkoxyphenyl‐nitrothiophene compounds 4a–d bearing diverse alkoxyl tails are described. The synthetic strategy was simply accomplished by alkali‐assisted alkylation of 4‐(5‐nitrothiophen‐2‐yl)phenol (3) with propyl, hexyl, nonyl, and/or dodecyl iodide. The molecular structures were determined using infrared (IR), 1H NMR, and mass spectroscopy. Ultraviolet–visible (UV–vis) absorption and emission spectra of the produced 4‐alkoxyphenyl‐nitrothiophenes revealed considerable extinction coefficients, which were shown to be controlled by the thiophene bridge in conjugation with the alkoxy donor moiety. It was found that the maximum absorbance wavelength was affected by the alkoxyl group‐bonded substituents. The antioxidant efficiency obtained from the 4‐alkoxyphenyl‐nitrothiophene hybrids was excellent compared with that widely used drugs [butylated hydroxytoluene (BHT) and vitamin C]. Unlike 2‐(4‐[dodecyloxy]phenyl)‐5‐nitrothiophene hybrid 4d, which has made solid claims about the good effect of its reference drugs and vitamins, Docking investigations of the prepared 4‐alkoxyphenyl‐nitrothiophene hybrids towards the selected 5IKQ protein revealed impressive coordination and antioxidant effectiveness.
2‐(4‐[Hexyloxy]phenyl)‐5‐nitrothiophene hybrid 4b displayed a fluorescence colour in dimethyl sulphoxide (DMSO) in UV spectra, better radical scavenging, and a rational docking score with S = −7.2694 kcal/mol and RMSD = 0.8550 in s molecular docking study towards PDB: 5IKQ.</abstract><cop>England</cop><pub>Wiley Subscription Services, Inc</pub><pmid>37259924</pmid><doi>10.1002/bio.4531</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-1805-5926</orcidid></addata></record> |
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| subjects | (4‐alkoxyphenyl)‐nitrothiophene 4‐(5‐nitrothiophen‐2‐yl)phenol Alkylation Analytical methods antioxidant Antioxidants Antioxidants - chemistry Ascorbic Acid Bridges Butylated hydroxytoluene Chemical Phenomena Chemical synthesis Coefficients Coloring Agents Conjugation Drugs Emission spectra Fluorescence hexyl iodide Hybrids Iodides Mass spectroscopy Molecular docking Molecular Docking Simulation Molecular Structure NMR Nuclear magnetic resonance Phenols pull–push Vitamins Wavelength |
| title | Synthesis, antioxidant, and molecular docking of new fluorescent (4‐alkoxyphenyl)‐nitrothiophene compounds |
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