Novel Schiff bases–based thiophenes: Design, synthesis and biological evaluation
2‐amino‐5‐(3‐fluoro‐4‐methoxyphenyl)thiophene‐3‐carbonitrile derivatives have been synthesized from 1‐(3‐fluoro‐4‐methoxyphenyl)ethanone, malononitrile, mild base, and sulfur powder using the Gewald method through a multistep reaction sequence. The structures of newly synthesized compounds were esta...
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| Veröffentlicht in: | Journal of the Chinese Chemical Society (Taipei) 2020-07, Vol.67 (7), p.1278-1288 |
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| container_title | Journal of the Chinese Chemical Society (Taipei) |
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| creator | Puthran, Divyaraj Poojary, Boja Nayak, Soukhyarani G. Purushotham, Nikil Bhat, Manjunath Hedge, Hemant |
| description | 2‐amino‐5‐(3‐fluoro‐4‐methoxyphenyl)thiophene‐3‐carbonitrile derivatives have been synthesized from 1‐(3‐fluoro‐4‐methoxyphenyl)ethanone, malononitrile, mild base, and sulfur powder using the Gewald method through a multistep reaction sequence. The structures of newly synthesized compounds were established on the basis of their elemental analyses, IR, 1H NMR, 13C NMR, and mass spectral data, and then synthesized compounds were screened for their in vitro antimicrobial activity. Among them, derivatives 3b (thiphene), 3f (pyrazole), and 3d (halogen) showed good activity and remaining derivatives exhibited moderate activity.
Literature reports for active derivatives of thiophene hybridized with substituted five, six and fused heterocyclic ring systems. |
| doi_str_mv | 10.1002/jccs.201900388 |
| format | Article |
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Literature reports for active derivatives of thiophene hybridized with substituted five, six and fused heterocyclic ring systems.</description><identifier>ISSN: 0009-4536</identifier><identifier>EISSN: 2192-6549</identifier><identifier>DOI: 10.1002/jccs.201900388</identifier><language>eng</language><publisher>Weinheim: Wiley‐VCH Verlag GmbH & Co. KGaA</publisher><subject>1‐(3‐fluoro‐4‐methoxyphenyl)ethanone ; antimicrobial ; Derivatives ; Gewald synthesis ; Imines ; Malononitrile ; NMR ; Nuclear magnetic resonance ; Pyrazole ; Schiff base ; Thiophenes</subject><ispartof>Journal of the Chinese Chemical Society (Taipei), 2020-07, Vol.67 (7), p.1278-1288</ispartof><rights>2020 The Chemical Society Located in Taipei & Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3548-baf70d6cf68401796c4ba2544d9b858c2858f22f820355b2a6ba90a771972d2f3</citedby><cites>FETCH-LOGICAL-c3548-baf70d6cf68401796c4ba2544d9b858c2858f22f820355b2a6ba90a771972d2f3</cites><orcidid>0000-0001-6725-3289</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%2Fjccs.201900388$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjccs.201900388$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Puthran, Divyaraj</creatorcontrib><creatorcontrib>Poojary, Boja</creatorcontrib><creatorcontrib>Nayak, Soukhyarani G.</creatorcontrib><creatorcontrib>Purushotham, Nikil</creatorcontrib><creatorcontrib>Bhat, Manjunath</creatorcontrib><creatorcontrib>Hedge, Hemant</creatorcontrib><title>Novel Schiff bases–based thiophenes: Design, synthesis and biological evaluation</title><title>Journal of the Chinese Chemical Society (Taipei)</title><description>2‐amino‐5‐(3‐fluoro‐4‐methoxyphenyl)thiophene‐3‐carbonitrile derivatives have been synthesized from 1‐(3‐fluoro‐4‐methoxyphenyl)ethanone, malononitrile, mild base, and sulfur powder using the Gewald method through a multistep reaction sequence. The structures of newly synthesized compounds were established on the basis of their elemental analyses, IR, 1H NMR, 13C NMR, and mass spectral data, and then synthesized compounds were screened for their in vitro antimicrobial activity. Among them, derivatives 3b (thiphene), 3f (pyrazole), and 3d (halogen) showed good activity and remaining derivatives exhibited moderate activity.
Literature reports for active derivatives of thiophene hybridized with substituted five, six and fused heterocyclic ring systems.</description><subject>1‐(3‐fluoro‐4‐methoxyphenyl)ethanone</subject><subject>antimicrobial</subject><subject>Derivatives</subject><subject>Gewald synthesis</subject><subject>Imines</subject><subject>Malononitrile</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Pyrazole</subject><subject>Schiff base</subject><subject>Thiophenes</subject><issn>0009-4536</issn><issn>2192-6549</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkD1PwzAQhi0EEqWwMltiJeVysRObDZVvVSBRmC3HsZtUIS5xWtSN_8A_5JeQqghGlntveJ476SXkOIZRDIBnc2PCCCGWAIkQO2SAscQo5UzukgEAyIjxJN0nByHMAViCXA7I04Nf2ZpOTVk5R3MdbPj6-NxkQbuy8ovSNjac00sbqllzSsO66cp-D1Q3Bc0rX_tZZXRN7UrXS91Vvjkke07XwR795JC8XF89j2-jyePN3fhiEpmEMxHl2mVQpMalgkGcydSwXCNnrJC54MJgPxyiEwgJ5znqNNcSdJbFMsMCXTIkJ9u7i9a_LW3o1Nwv26Z_qZAhsoQLyXpqtKVM60NorVOLtnrV7VrFoDa9qU1v6re3XpBb4b2q7fofWt2Px9M_9xt3nnJG</recordid><startdate>202007</startdate><enddate>202007</enddate><creator>Puthran, Divyaraj</creator><creator>Poojary, Boja</creator><creator>Nayak, Soukhyarani G.</creator><creator>Purushotham, Nikil</creator><creator>Bhat, Manjunath</creator><creator>Hedge, Hemant</creator><general>Wiley‐VCH Verlag GmbH & Co. KGaA</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-6725-3289</orcidid></search><sort><creationdate>202007</creationdate><title>Novel Schiff bases–based thiophenes: Design, synthesis and biological evaluation</title><author>Puthran, Divyaraj ; Poojary, Boja ; Nayak, Soukhyarani G. ; Purushotham, Nikil ; Bhat, Manjunath ; Hedge, Hemant</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3548-baf70d6cf68401796c4ba2544d9b858c2858f22f820355b2a6ba90a771972d2f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>1‐(3‐fluoro‐4‐methoxyphenyl)ethanone</topic><topic>antimicrobial</topic><topic>Derivatives</topic><topic>Gewald synthesis</topic><topic>Imines</topic><topic>Malononitrile</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Pyrazole</topic><topic>Schiff base</topic><topic>Thiophenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Puthran, Divyaraj</creatorcontrib><creatorcontrib>Poojary, Boja</creatorcontrib><creatorcontrib>Nayak, Soukhyarani G.</creatorcontrib><creatorcontrib>Purushotham, Nikil</creatorcontrib><creatorcontrib>Bhat, Manjunath</creatorcontrib><creatorcontrib>Hedge, Hemant</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of the Chinese Chemical Society (Taipei)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Puthran, Divyaraj</au><au>Poojary, Boja</au><au>Nayak, Soukhyarani G.</au><au>Purushotham, Nikil</au><au>Bhat, Manjunath</au><au>Hedge, Hemant</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Schiff bases–based thiophenes: Design, synthesis and biological evaluation</atitle><jtitle>Journal of the Chinese Chemical Society (Taipei)</jtitle><date>2020-07</date><risdate>2020</risdate><volume>67</volume><issue>7</issue><spage>1278</spage><epage>1288</epage><pages>1278-1288</pages><issn>0009-4536</issn><eissn>2192-6549</eissn><abstract>2‐amino‐5‐(3‐fluoro‐4‐methoxyphenyl)thiophene‐3‐carbonitrile derivatives have been synthesized from 1‐(3‐fluoro‐4‐methoxyphenyl)ethanone, malononitrile, mild base, and sulfur powder using the Gewald method through a multistep reaction sequence. The structures of newly synthesized compounds were established on the basis of their elemental analyses, IR, 1H NMR, 13C NMR, and mass spectral data, and then synthesized compounds were screened for their in vitro antimicrobial activity. Among them, derivatives 3b (thiphene), 3f (pyrazole), and 3d (halogen) showed good activity and remaining derivatives exhibited moderate activity.
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| subjects | 1‐(3‐fluoro‐4‐methoxyphenyl)ethanone antimicrobial Derivatives Gewald synthesis Imines Malononitrile NMR Nuclear magnetic resonance Pyrazole Schiff base Thiophenes |
| title | Novel Schiff bases–based thiophenes: Design, synthesis and biological evaluation |
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