One Pot Synthesis and Biological Activity Studies of New Spirooxindoles
This article reports one‐pot synthesis of ten novel spirooxindoles using 5‐methyl‐2‐thiohydantoin, isatin derivatives, and malononitrile in good to high yields (65‐90 %). The structures of the synthesized compounds were deduced by 1H‐NMR, 13C NMR, FT‐IR, and Mass spectral data. The antibacterial act...
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| Veröffentlicht in: | Chemistry & biodiversity 2024-06, Vol.21 (6), p.e202301942-n/a |
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| creator | Omidvar, Amir Reza Asghari, Sakineh Ghasempour, Leila Mohseni, Mojtaba |
| description | This article reports one‐pot synthesis of ten novel spirooxindoles using 5‐methyl‐2‐thiohydantoin, isatin derivatives, and malononitrile in good to high yields (65‐90 %). The structures of the synthesized compounds were deduced by 1H‐NMR, 13C NMR, FT‐IR, and Mass spectral data. The antibacterial activity of the compounds was evaluated against two Gram‐positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram‐negative bacteria (Escherichia coli and Pseudomonas aeruginosa) based on the Kirby‐Bauer method. According to the obtained data, the synthesized compounds show more activity against Gram‐positive bacteria than Gram‐negative bacteria. Also, the antioxidant activity of these compounds was measured using the DPPH radical scavenging test method, which showed good to excellent activity (59.65–94.03 %). Among them, the chlorinated derivatives (4 f–j) exhibited more antioxidant activity (84.85–94.03 %) than the other compounds (4 a–e) (56.65–74.4 %) and even ascorbic acid as a standard antioxidant compound (82.3 %). |
| doi_str_mv | 10.1002/cbdv.202301942 |
| format | Article |
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The structures of the synthesized compounds were deduced by 1H‐NMR, 13C NMR, FT‐IR, and Mass spectral data. The antibacterial activity of the compounds was evaluated against two Gram‐positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram‐negative bacteria (Escherichia coli and Pseudomonas aeruginosa) based on the Kirby‐Bauer method. According to the obtained data, the synthesized compounds show more activity against Gram‐positive bacteria than Gram‐negative bacteria. Also, the antioxidant activity of these compounds was measured using the DPPH radical scavenging test method, which showed good to excellent activity (59.65–94.03 %). Among them, the chlorinated derivatives (4 f–j) exhibited more antioxidant activity (84.85–94.03 %) than the other compounds (4 a–e) (56.65–74.4 %) and even ascorbic acid as a standard antioxidant compound (82.3 %).</description><identifier>ISSN: 1612-1872</identifier><identifier>ISSN: 1612-1880</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.202301942</identifier><identifier>PMID: 38393713</identifier><language>eng</language><publisher>Switzerland: Wiley Subscription Services, Inc</publisher><subject>2-Thiohydantoin ; Anti-bacterial ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Anti-oxidant ; Antibacterial activity ; Antioxidants ; Antioxidants - chemical synthesis ; Antioxidants - chemistry ; Antioxidants - pharmacology ; Ascorbic acid ; Biological activity ; Biphenyl Compounds - antagonists & inhibitors ; Biphenyl Compounds - chemistry ; Coliforms ; E coli ; Gram-negative bacteria ; Gram-Negative Bacteria - drug effects ; Gram-Positive Bacteria - drug effects ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; Isatin - chemical synthesis ; Isatin - chemistry ; Isatin - pharmacology ; Isatins ; Malononitrile ; Microbial Sensitivity Tests ; Molecular Structure ; NMR ; Nuclear magnetic resonance ; Oxindoles - chemical synthesis ; Oxindoles - chemistry ; Oxindoles - pharmacology ; Picrates - antagonists & inhibitors ; Pseudomonas aeruginosa - drug effects ; Scavenging ; Spiro Compounds - chemical synthesis ; Spiro Compounds - chemistry ; Spiro Compounds - pharmacology ; Spirooxindoles ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship ; Synthesis</subject><ispartof>Chemistry & biodiversity, 2024-06, Vol.21 (6), p.e202301942-n/a</ispartof><rights>2024 Wiley-VHCA AG, Zurich, Switzerland</rights><rights>2024 Wiley-VHCA AG, Zurich, Switzerland.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3282-d3652558e69c8cd46a306a87ac9d77edf823b4533212652c587f62f1e52ef0743</cites><orcidid>0000-0002-6608-9525</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%2Fcbdv.202301942$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.202301942$$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/38393713$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Omidvar, Amir Reza</creatorcontrib><creatorcontrib>Asghari, Sakineh</creatorcontrib><creatorcontrib>Ghasempour, Leila</creatorcontrib><creatorcontrib>Mohseni, Mojtaba</creatorcontrib><title>One Pot Synthesis and Biological Activity Studies of New Spirooxindoles</title><title>Chemistry & biodiversity</title><addtitle>Chem Biodivers</addtitle><description>This article reports one‐pot synthesis of ten novel spirooxindoles using 5‐methyl‐2‐thiohydantoin, isatin derivatives, and malononitrile in good to high yields (65‐90 %). The structures of the synthesized compounds were deduced by 1H‐NMR, 13C NMR, FT‐IR, and Mass spectral data. The antibacterial activity of the compounds was evaluated against two Gram‐positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram‐negative bacteria (Escherichia coli and Pseudomonas aeruginosa) based on the Kirby‐Bauer method. According to the obtained data, the synthesized compounds show more activity against Gram‐positive bacteria than Gram‐negative bacteria. Also, the antioxidant activity of these compounds was measured using the DPPH radical scavenging test method, which showed good to excellent activity (59.65–94.03 %). Among them, the chlorinated derivatives (4 f–j) exhibited more antioxidant activity (84.85–94.03 %) than the other compounds (4 a–e) (56.65–74.4 %) and even ascorbic acid as a standard antioxidant compound (82.3 %).</description><subject>2-Thiohydantoin</subject><subject>Anti-bacterial</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Anti-oxidant</subject><subject>Antibacterial activity</subject><subject>Antioxidants</subject><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - pharmacology</subject><subject>Ascorbic acid</subject><subject>Biological activity</subject><subject>Biphenyl Compounds - antagonists & inhibitors</subject><subject>Biphenyl Compounds - chemistry</subject><subject>Coliforms</subject><subject>E coli</subject><subject>Gram-negative bacteria</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Isatin - chemical synthesis</subject><subject>Isatin - chemistry</subject><subject>Isatin - pharmacology</subject><subject>Isatins</subject><subject>Malononitrile</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Oxindoles - chemical synthesis</subject><subject>Oxindoles - chemistry</subject><subject>Oxindoles - pharmacology</subject><subject>Picrates - antagonists & inhibitors</subject><subject>Pseudomonas aeruginosa - drug effects</subject><subject>Scavenging</subject><subject>Spiro Compounds - chemical synthesis</subject><subject>Spiro Compounds - chemistry</subject><subject>Spiro Compounds - pharmacology</subject><subject>Spirooxindoles</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>Synthesis</subject><issn>1612-1872</issn><issn>1612-1880</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0M1PwjAYBvDGaETRq0fTxIuXYT-2rj0CKpoQMUG9NqPttGSsuG7g_ntLQEy8eOqb5vc-efMAcIFRDyNEbtRMr3oEEYqwiMkBOMEMkwhzjg73c0o64NT7efDhnx-DDuVU0BTTEzCalAY-uxpO27L-MN56mJUaDqwr3LtVWQH7qrYrW7dwWjfaGg9dDp_MGk6XtnLuy5baFcafgaM8K7w5371d8Hp_9zJ8iMaT0eOwP44UJZxEmrKEJAk3TCiudMwyiljG00wJnaZG55zQWZxQSjAJUiU8zRnJsUmIyVEa0y643uYuK_fZGF_LhfXKFEVWGtd4SVGCQhGCkUCv_tC5a6oyXBcUE1gQLjaqt1Wqct5XJpfLyi6yqpUYyU3FclOx3FccFi53sc1sYfSe_3QagNiCtS1M-0-cHA5u337DvwG_FIXj</recordid><startdate>202406</startdate><enddate>202406</enddate><creator>Omidvar, Amir Reza</creator><creator>Asghari, Sakineh</creator><creator>Ghasempour, Leila</creator><creator>Mohseni, Mojtaba</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>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6608-9525</orcidid></search><sort><creationdate>202406</creationdate><title>One Pot Synthesis and Biological Activity Studies of New Spirooxindoles</title><author>Omidvar, Amir Reza ; Asghari, Sakineh ; Ghasempour, Leila ; Mohseni, Mojtaba</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3282-d3652558e69c8cd46a306a87ac9d77edf823b4533212652c587f62f1e52ef0743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>2-Thiohydantoin</topic><topic>Anti-bacterial</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Anti-oxidant</topic><topic>Antibacterial activity</topic><topic>Antioxidants</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - pharmacology</topic><topic>Ascorbic acid</topic><topic>Biological activity</topic><topic>Biphenyl Compounds - antagonists & inhibitors</topic><topic>Biphenyl Compounds - chemistry</topic><topic>Coliforms</topic><topic>E coli</topic><topic>Gram-negative bacteria</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Isatin - chemical synthesis</topic><topic>Isatin - chemistry</topic><topic>Isatin - pharmacology</topic><topic>Isatins</topic><topic>Malononitrile</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Oxindoles - chemical synthesis</topic><topic>Oxindoles - chemistry</topic><topic>Oxindoles - pharmacology</topic><topic>Picrates - antagonists & inhibitors</topic><topic>Pseudomonas aeruginosa - drug effects</topic><topic>Scavenging</topic><topic>Spiro Compounds - chemical synthesis</topic><topic>Spiro Compounds - chemistry</topic><topic>Spiro Compounds - pharmacology</topic><topic>Spirooxindoles</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Omidvar, Amir Reza</creatorcontrib><creatorcontrib>Asghari, Sakineh</creatorcontrib><creatorcontrib>Ghasempour, Leila</creatorcontrib><creatorcontrib>Mohseni, Mojtaba</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Omidvar, Amir Reza</au><au>Asghari, Sakineh</au><au>Ghasempour, Leila</au><au>Mohseni, Mojtaba</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One Pot Synthesis and Biological Activity Studies of New Spirooxindoles</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2024-06</date><risdate>2024</risdate><volume>21</volume><issue>6</issue><spage>e202301942</spage><epage>n/a</epage><pages>e202301942-n/a</pages><issn>1612-1872</issn><issn>1612-1880</issn><eissn>1612-1880</eissn><abstract>This article reports one‐pot synthesis of ten novel spirooxindoles using 5‐methyl‐2‐thiohydantoin, isatin derivatives, and malononitrile in good to high yields (65‐90 %). The structures of the synthesized compounds were deduced by 1H‐NMR, 13C NMR, FT‐IR, and Mass spectral data. The antibacterial activity of the compounds was evaluated against two Gram‐positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram‐negative bacteria (Escherichia coli and Pseudomonas aeruginosa) based on the Kirby‐Bauer method. According to the obtained data, the synthesized compounds show more activity against Gram‐positive bacteria than Gram‐negative bacteria. Also, the antioxidant activity of these compounds was measured using the DPPH radical scavenging test method, which showed good to excellent activity (59.65–94.03 %). Among them, the chlorinated derivatives (4 f–j) exhibited more antioxidant activity (84.85–94.03 %) than the other compounds (4 a–e) (56.65–74.4 %) and even ascorbic acid as a standard antioxidant compound (82.3 %).</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>38393713</pmid><doi>10.1002/cbdv.202301942</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-6608-9525</orcidid></addata></record> |
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| subjects | 2-Thiohydantoin Anti-bacterial Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Anti-oxidant Antibacterial activity Antioxidants Antioxidants - chemical synthesis Antioxidants - chemistry Antioxidants - pharmacology Ascorbic acid Biological activity Biphenyl Compounds - antagonists & inhibitors Biphenyl Compounds - chemistry Coliforms E coli Gram-negative bacteria Gram-Negative Bacteria - drug effects Gram-Positive Bacteria - drug effects Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Isatin - chemical synthesis Isatin - chemistry Isatin - pharmacology Isatins Malononitrile Microbial Sensitivity Tests Molecular Structure NMR Nuclear magnetic resonance Oxindoles - chemical synthesis Oxindoles - chemistry Oxindoles - pharmacology Picrates - antagonists & inhibitors Pseudomonas aeruginosa - drug effects Scavenging Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Spiro Compounds - pharmacology Spirooxindoles Staphylococcus aureus - drug effects Structure-Activity Relationship Synthesis |
| title | One Pot Synthesis and Biological Activity Studies of New Spirooxindoles |
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