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Experimental and theoretical investigations on a furan‐2‐carboxamide‐bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity
A thiazole‐based heterocyclic amide, namely, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, C8H6N2O2S, was synthesized and investigated for its antimicrobial activity. The structure was characterized by elemental analysis and IR, 1H NMR, and 13C NMR spectroscopy. The molecular and electronic structures were i...
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Published in: | Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2022-03, Vol.78 (3), p.201-211 |
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container_title | Acta crystallographica. Section C, Crystal structure communications |
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description | A thiazole‐based heterocyclic amide, namely, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, C8H6N2O2S, was synthesized and investigated for its antimicrobial activity. The structure was characterized by elemental analysis and IR, 1H NMR, and 13C NMR spectroscopy. The molecular and electronic structures were investigated experimentally by single‐crystal X‐ray diffraction (XRD) and theoretically by density functional theory (DFT) modelling. The compound crystallized in the monoclinic space group P21/n and the asymmetric unit contains two symmetrically independent molecules. Several noncovalent interactions were recorded by XRD and analysed with Hirshfeld surface analysis (HSA) calculations. Natural bond orbital, molecular electrostatic potential, second‐order nonlinear optical and thermodynamic property analyses were also carried out using the DFT/B3LYP method. The title compound was evaluated for antimicrobial activity against eight microorganisms consisting of Gram‐negative bacteria, Gram‐positive bacteria and fungi. The compound showed good antimicrobial activity against the eight tested microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.
A thiazole‐based heterocyclic amide, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, was synthesized and investigated for its antimicrobial activity against eight microorganisms and showed good activity against all eight microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications. |
doi_str_mv | 10.1107/S2053229622002066 |
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A thiazole‐based heterocyclic amide, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, was synthesized and investigated for its antimicrobial activity against eight microorganisms and showed good activity against all eight microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.</description><identifier>ISSN: 2053-2296</identifier><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 2053-2296</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S2053229622002066</identifier><identifier>PMID: 35245217</identifier><language>eng</language><publisher>5 Abbey Square, Chester, Cheshire CH1 2HU, England: International Union of Crystallography</publisher><subject>Antiinfectives and antibacterials ; antimicrobial activity ; Antimicrobial agents ; Bacteria ; Biological activity ; carboxamide ; Chemical analysis ; Chemical bonds ; Chemical synthesis ; Crystal structure ; Crystallization ; Crystallography, X-Ray ; Density functional theory ; Electronics ; furan ; Furans - pharmacology ; Hirshfeld surface ; Hydrogen Bonding ; Infrared analysis ; Infrared spectroscopy ; Investigations ; Magnetic Resonance Spectroscopy ; Microorganisms ; NMR spectroscopy ; Optical properties ; spectroscopic evaluation ; Spectroscopy, Fourier Transform Infrared ; Surface analysis (chemical) ; thiazolamide ; Thiazoles - chemistry ; Thiazoles - pharmacology ; X-ray diffraction ; XRD</subject><ispartof>Acta crystallographica. Section C, Crystal structure communications, 2022-03, Vol.78 (3), p.201-211</ispartof><rights>2022 Çakmak et al. published by IUCr Journals.</rights><rights>Copyright Wiley Subscription Services, Inc. Mar 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3798-fe0a670900426430878c22d17b6ed3f5ded9a08f2a92211449270e0cc74223163</citedby><cites>FETCH-LOGICAL-c3798-fe0a670900426430878c22d17b6ed3f5ded9a08f2a92211449270e0cc74223163</cites><orcidid>0000-0002-1406-5513 ; 0000-0001-7754-9059 ; 0000-0002-4428-4696</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35245217$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Çakmak, Şükriye</creatorcontrib><creatorcontrib>Koşar Kırca, Başak</creatorcontrib><creatorcontrib>Veyisoğlu, Aysel</creatorcontrib><creatorcontrib>Yakan, Hasan</creatorcontrib><creatorcontrib>Ersanlı, Cem Cüneyt</creatorcontrib><creatorcontrib>Kütük, Halil</creatorcontrib><title>Experimental and theoretical investigations on a furan‐2‐carboxamide‐bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity</title><title>Acta crystallographica. Section C, Crystal structure communications</title><addtitle>Acta Crystallogr C Struct Chem</addtitle><description>A thiazole‐based heterocyclic amide, namely, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, C8H6N2O2S, was synthesized and investigated for its antimicrobial activity. The structure was characterized by elemental analysis and IR, 1H NMR, and 13C NMR spectroscopy. The molecular and electronic structures were investigated experimentally by single‐crystal X‐ray diffraction (XRD) and theoretically by density functional theory (DFT) modelling. The compound crystallized in the monoclinic space group P21/n and the asymmetric unit contains two symmetrically independent molecules. Several noncovalent interactions were recorded by XRD and analysed with Hirshfeld surface analysis (HSA) calculations. Natural bond orbital, molecular electrostatic potential, second‐order nonlinear optical and thermodynamic property analyses were also carried out using the DFT/B3LYP method. The title compound was evaluated for antimicrobial activity against eight microorganisms consisting of Gram‐negative bacteria, Gram‐positive bacteria and fungi. The compound showed good antimicrobial activity against the eight tested microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.
A thiazole‐based heterocyclic amide, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, was synthesized and investigated for its antimicrobial activity against eight microorganisms and showed good activity against all eight microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.</description><subject>Antiinfectives and antibacterials</subject><subject>antimicrobial activity</subject><subject>Antimicrobial agents</subject><subject>Bacteria</subject><subject>Biological activity</subject><subject>carboxamide</subject><subject>Chemical analysis</subject><subject>Chemical bonds</subject><subject>Chemical synthesis</subject><subject>Crystal structure</subject><subject>Crystallization</subject><subject>Crystallography, X-Ray</subject><subject>Density functional theory</subject><subject>Electronics</subject><subject>furan</subject><subject>Furans - pharmacology</subject><subject>Hirshfeld surface</subject><subject>Hydrogen Bonding</subject><subject>Infrared analysis</subject><subject>Infrared spectroscopy</subject><subject>Investigations</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Microorganisms</subject><subject>NMR spectroscopy</subject><subject>Optical properties</subject><subject>spectroscopic evaluation</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>Surface analysis (chemical)</subject><subject>thiazolamide</subject><subject>Thiazoles - chemistry</subject><subject>Thiazoles - pharmacology</subject><subject>X-ray diffraction</subject><subject>XRD</subject><issn>2053-2296</issn><issn>0108-2701</issn><issn>2053-2296</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFksFu1DAQhiMEolXpA3BBlrhw2O3a4yROuFXbllYqVFqKBFwix5nsuvLaWzspTU99BJ6RE4-Bd7cgBEgcLHtG3_wz45kkec7oAWNUTN4DzThAmQNQCjTPHyW7a9d47Xv823sn2Q_hilLKGGRCsKfJDs8gzYCJ3eT78e0KvV6i7aQh0jakW6Dz2GkVbW1vMHR6LjvtbCDOEkna3kv77f4rxKOkr92tXOoGo1Wj9NrOo4KWd87gaxIGG-WCDiOyjA7VG-mJWkgvVRez3m10ST2Qs9nk3dvZ5OPsaEQwgp13Vqt_okcnlyNyqn1YtGgaEnrfSoWxdGmGmGnTQ62dcfNNCzFc3-hueJY8aaUJuP9w7yUfTo4vp6fj84s3Z9PD87HioizGLVKZC1pSmkKeclqIQgE0TNQ5NrzNGmxKSYsWZAnAWJqWIChSpUQKwFnO95JXW92Vd9d9_L1qqYNCY6RF14cKcp6zNM8yiOjLP9Ar1_vYx4aKBKO8iBTbUsq7EDy21SrOS_qhYrRab0L11ybEmBcPyn29xOZXxM-5R6DcAl-0weH_itXhpyl8vuCUFfwHsGPElw</recordid><startdate>202203</startdate><enddate>202203</enddate><creator>Çakmak, Şükriye</creator><creator>Koşar Kırca, Başak</creator><creator>Veyisoğlu, Aysel</creator><creator>Yakan, Hasan</creator><creator>Ersanlı, Cem Cüneyt</creator><creator>Kütük, Halil</creator><general>International Union of Crystallography</general><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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1406-5513</orcidid><orcidid>https://orcid.org/0000-0001-7754-9059</orcidid><orcidid>https://orcid.org/0000-0002-4428-4696</orcidid></search><sort><creationdate>202203</creationdate><title>Experimental and theoretical investigations on a furan‐2‐carboxamide‐bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity</title><author>Çakmak, Şükriye ; Koşar Kırca, Başak ; Veyisoğlu, Aysel ; Yakan, Hasan ; Ersanlı, Cem Cüneyt ; Kütük, Halil</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3798-fe0a670900426430878c22d17b6ed3f5ded9a08f2a92211449270e0cc74223163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Antiinfectives and antibacterials</topic><topic>antimicrobial activity</topic><topic>Antimicrobial agents</topic><topic>Bacteria</topic><topic>Biological activity</topic><topic>carboxamide</topic><topic>Chemical analysis</topic><topic>Chemical bonds</topic><topic>Chemical synthesis</topic><topic>Crystal structure</topic><topic>Crystallization</topic><topic>Crystallography, X-Ray</topic><topic>Density functional theory</topic><topic>Electronics</topic><topic>furan</topic><topic>Furans - pharmacology</topic><topic>Hirshfeld surface</topic><topic>Hydrogen Bonding</topic><topic>Infrared analysis</topic><topic>Infrared spectroscopy</topic><topic>Investigations</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Microorganisms</topic><topic>NMR spectroscopy</topic><topic>Optical properties</topic><topic>spectroscopic evaluation</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Surface analysis (chemical)</topic><topic>thiazolamide</topic><topic>Thiazoles - chemistry</topic><topic>Thiazoles - pharmacology</topic><topic>X-ray diffraction</topic><topic>XRD</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Çakmak, Şükriye</creatorcontrib><creatorcontrib>Koşar Kırca, Başak</creatorcontrib><creatorcontrib>Veyisoğlu, Aysel</creatorcontrib><creatorcontrib>Yakan, Hasan</creatorcontrib><creatorcontrib>Ersanlı, Cem Cüneyt</creatorcontrib><creatorcontrib>Kütük, Halil</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><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><collection>MEDLINE - Academic</collection><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Çakmak, Şükriye</au><au>Koşar Kırca, Başak</au><au>Veyisoğlu, Aysel</au><au>Yakan, Hasan</au><au>Ersanlı, Cem Cüneyt</au><au>Kütük, Halil</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Experimental and theoretical investigations on a furan‐2‐carboxamide‐bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><addtitle>Acta Crystallogr C Struct Chem</addtitle><date>2022-03</date><risdate>2022</risdate><volume>78</volume><issue>3</issue><spage>201</spage><epage>211</epage><pages>201-211</pages><issn>2053-2296</issn><issn>0108-2701</issn><eissn>2053-2296</eissn><eissn>1600-5759</eissn><abstract>A thiazole‐based heterocyclic amide, namely, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, C8H6N2O2S, was synthesized and investigated for its antimicrobial activity. The structure was characterized by elemental analysis and IR, 1H NMR, and 13C NMR spectroscopy. The molecular and electronic structures were investigated experimentally by single‐crystal X‐ray diffraction (XRD) and theoretically by density functional theory (DFT) modelling. The compound crystallized in the monoclinic space group P21/n and the asymmetric unit contains two symmetrically independent molecules. Several noncovalent interactions were recorded by XRD and analysed with Hirshfeld surface analysis (HSA) calculations. Natural bond orbital, molecular electrostatic potential, second‐order nonlinear optical and thermodynamic property analyses were also carried out using the DFT/B3LYP method. The title compound was evaluated for antimicrobial activity against eight microorganisms consisting of Gram‐negative bacteria, Gram‐positive bacteria and fungi. The compound showed good antimicrobial activity against the eight tested microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.
A thiazole‐based heterocyclic amide, N‐(thiazol‐2‐yl)furan‐2‐carboxamide, was synthesized and investigated for its antimicrobial activity against eight microorganisms and showed good activity against all eight microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.</abstract><cop>5 Abbey Square, Chester, Cheshire CH1 2HU, England</cop><pub>International Union of Crystallography</pub><pmid>35245217</pmid><doi>10.1107/S2053229622002066</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-1406-5513</orcidid><orcidid>https://orcid.org/0000-0001-7754-9059</orcidid><orcidid>https://orcid.org/0000-0002-4428-4696</orcidid></addata></record> |
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subjects | Antiinfectives and antibacterials antimicrobial activity Antimicrobial agents Bacteria Biological activity carboxamide Chemical analysis Chemical bonds Chemical synthesis Crystal structure Crystallization Crystallography, X-Ray Density functional theory Electronics furan Furans - pharmacology Hirshfeld surface Hydrogen Bonding Infrared analysis Infrared spectroscopy Investigations Magnetic Resonance Spectroscopy Microorganisms NMR spectroscopy Optical properties spectroscopic evaluation Spectroscopy, Fourier Transform Infrared Surface analysis (chemical) thiazolamide Thiazoles - chemistry Thiazoles - pharmacology X-ray diffraction XRD |
title | Experimental and theoretical investigations on a furan‐2‐carboxamide‐bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity |
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