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Novel imidazole derivatives as antifungal agents: Synthesis, biological evaluation, ADME prediction and molecular docking studies
A series of 2-(substituteddithiocarbamoyl)-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide derivatives was designed and synthesized to combat the increasing incidence of drug-resistant fungal infections. All synthesized compounds were characterized by IR, 1 H-NMR, 13 C-NMR, and HRMS spectra and elem...
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Published in: | Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2019-09, Vol.194 (9), p.887-894 |
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container_title | Phosphorus, sulfur, and silicon and the related elements |
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creator | Altindag, Firuze Diyar Saglik, Begüm Nurpelin Acar Çevik, Ulviye Isikdag, Ilhan Özkay, Yusuf Karaca Gençer, Hülya |
description | A series of 2-(substituteddithiocarbamoyl)-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide derivatives was designed and synthesized to combat the increasing incidence of drug-resistant fungal infections. All synthesized compounds were characterized by IR,
1
H-NMR,
13
C-NMR, and HRMS spectra and elemental analyses. Antifungal activity tests were performed against four different fungal strains. Molecular docking studies were performed to investigate the mode of action towards the fungal lanosterol 14α-demethylase, a cytochrome P450-dependent enzyme. ADME studies were carried out and a connection between activities and physicochemical properties of the target compounds was determined. Most of the final compounds exhibited significant activity against Candida albicans and Candida krusei with MIC
50
value 12.5 μg/mL. The results of in vitro anti-Candida activity, a docking study and ADME prediction revealed that the newly synthesized compounds have potential anti-Candida activity and evidenced the most active derivative, 5b (2-Pyrrolidinthiocarbonylthio-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide), which can be further optimized as a lead compound. |
doi_str_mv | 10.1080/10426507.2019.1565761 |
format | article |
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1
H-NMR,
13
C-NMR, and HRMS spectra and elemental analyses. Antifungal activity tests were performed against four different fungal strains. Molecular docking studies were performed to investigate the mode of action towards the fungal lanosterol 14α-demethylase, a cytochrome P450-dependent enzyme. ADME studies were carried out and a connection between activities and physicochemical properties of the target compounds was determined. Most of the final compounds exhibited significant activity against Candida albicans and Candida krusei with MIC
50
value 12.5 μg/mL. The results of in vitro anti-Candida activity, a docking study and ADME prediction revealed that the newly synthesized compounds have potential anti-Candida activity and evidenced the most active derivative, 5b (2-Pyrrolidinthiocarbonylthio-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide), which can be further optimized as a lead compound.</description><identifier>ISSN: 1042-6507</identifier><identifier>EISSN: 1563-5325</identifier><identifier>DOI: 10.1080/10426507.2019.1565761</identifier><language>eng</language><publisher>Abingdon: Taylor & Francis</publisher><subject>antifungal activity ; Antifungal agents ; Chemical synthesis ; Cytochromes P450 ; Derivatives ; dithiocarbamate ; Fungi ; Fungicides ; Imidazole ; Lead compounds ; Molecular docking ; NMR ; Nuclear magnetic resonance</subject><ispartof>Phosphorus, sulfur, and silicon and the related elements, 2019-09, Vol.194 (9), p.887-894</ispartof><rights>2019 Taylor & Francis Group, LLC 2019</rights><rights>2019 Taylor & Francis Group, LLC</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c338t-c77faebb2e3e4069d47fb8f35bcd1dd7c310f8ff2819451a0080d4a28e750b413</citedby><cites>FETCH-LOGICAL-c338t-c77faebb2e3e4069d47fb8f35bcd1dd7c310f8ff2819451a0080d4a28e750b413</cites><orcidid>0000-0002-0151-6266</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></links><search><creatorcontrib>Altindag, Firuze Diyar</creatorcontrib><creatorcontrib>Saglik, Begüm Nurpelin</creatorcontrib><creatorcontrib>Acar Çevik, Ulviye</creatorcontrib><creatorcontrib>Isikdag, Ilhan</creatorcontrib><creatorcontrib>Özkay, Yusuf</creatorcontrib><creatorcontrib>Karaca Gençer, Hülya</creatorcontrib><title>Novel imidazole derivatives as antifungal agents: Synthesis, biological evaluation, ADME prediction and molecular docking studies</title><title>Phosphorus, sulfur, and silicon and the related elements</title><description>A series of 2-(substituteddithiocarbamoyl)-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide derivatives was designed and synthesized to combat the increasing incidence of drug-resistant fungal infections. All synthesized compounds were characterized by IR,
1
H-NMR,
13
C-NMR, and HRMS spectra and elemental analyses. Antifungal activity tests were performed against four different fungal strains. Molecular docking studies were performed to investigate the mode of action towards the fungal lanosterol 14α-demethylase, a cytochrome P450-dependent enzyme. ADME studies were carried out and a connection between activities and physicochemical properties of the target compounds was determined. Most of the final compounds exhibited significant activity against Candida albicans and Candida krusei with MIC
50
value 12.5 μg/mL. The results of in vitro anti-Candida activity, a docking study and ADME prediction revealed that the newly synthesized compounds have potential anti-Candida activity and evidenced the most active derivative, 5b (2-Pyrrolidinthiocarbonylthio-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide), which can be further optimized as a lead compound.</description><subject>antifungal activity</subject><subject>Antifungal agents</subject><subject>Chemical synthesis</subject><subject>Cytochromes P450</subject><subject>Derivatives</subject><subject>dithiocarbamate</subject><subject>Fungi</subject><subject>Fungicides</subject><subject>Imidazole</subject><subject>Lead compounds</subject><subject>Molecular docking</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><issn>1042-6507</issn><issn>1563-5325</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kFtLAzEQhRdR8PoThICvbs1ls9n6ZKn1Al4e1OeQzaWmpklNdiv1zX9uSuurMDDDzDln4CuKUwQHCDbwAsEK1xSyAYZoOEC0pqxGO8VBnkhJCaa7ec6aci3aLw5TmkEIh5jAg-LnKSy1A3ZulfgOTgOlo12Kzi51AiKX76zp_VQ4IKbad-kSvKx8966TTeegtcGFqZX5qpfC9dkX_DkYXT9OwCJqZeV6kUMUmOdw2TsRgQryw_opSF2vrE7HxZ4RLumTbT8q3m4mr-O78uH59n48eiglIU1XSsaM0G2LNdEVrIeqYqZtDKGtVEgpJgmCpjEGN2hYUSRgJqMqgRvNKGwrRI6Ks03uIobPXqeOz0IffX7JMWaYQUxqklV0o5IxpBS14Yto5yKuOIJ8TZv_0eZr2nxLO_uuNj7rTYhz8RWiU7wTKxeiicJLmzj5P-IXo9KIqw</recordid><startdate>20190902</startdate><enddate>20190902</enddate><creator>Altindag, Firuze Diyar</creator><creator>Saglik, Begüm Nurpelin</creator><creator>Acar Çevik, Ulviye</creator><creator>Isikdag, Ilhan</creator><creator>Özkay, Yusuf</creator><creator>Karaca Gençer, Hülya</creator><general>Taylor & Francis</general><general>Taylor & Francis Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-0151-6266</orcidid></search><sort><creationdate>20190902</creationdate><title>Novel imidazole derivatives as antifungal agents: Synthesis, biological evaluation, ADME prediction and molecular docking studies</title><author>Altindag, Firuze Diyar ; Saglik, Begüm Nurpelin ; Acar Çevik, Ulviye ; Isikdag, Ilhan ; Özkay, Yusuf ; Karaca Gençer, Hülya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c338t-c77faebb2e3e4069d47fb8f35bcd1dd7c310f8ff2819451a0080d4a28e750b413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>antifungal activity</topic><topic>Antifungal agents</topic><topic>Chemical synthesis</topic><topic>Cytochromes P450</topic><topic>Derivatives</topic><topic>dithiocarbamate</topic><topic>Fungi</topic><topic>Fungicides</topic><topic>Imidazole</topic><topic>Lead compounds</topic><topic>Molecular docking</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Altindag, Firuze Diyar</creatorcontrib><creatorcontrib>Saglik, Begüm Nurpelin</creatorcontrib><creatorcontrib>Acar Çevik, Ulviye</creatorcontrib><creatorcontrib>Isikdag, Ilhan</creatorcontrib><creatorcontrib>Özkay, Yusuf</creatorcontrib><creatorcontrib>Karaca Gençer, Hülya</creatorcontrib><collection>CrossRef</collection><jtitle>Phosphorus, sulfur, and silicon and the related elements</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Altindag, Firuze Diyar</au><au>Saglik, Begüm Nurpelin</au><au>Acar Çevik, Ulviye</au><au>Isikdag, Ilhan</au><au>Özkay, Yusuf</au><au>Karaca Gençer, Hülya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel imidazole derivatives as antifungal agents: Synthesis, biological evaluation, ADME prediction and molecular docking studies</atitle><jtitle>Phosphorus, sulfur, and silicon and the related elements</jtitle><date>2019-09-02</date><risdate>2019</risdate><volume>194</volume><issue>9</issue><spage>887</spage><epage>894</epage><pages>887-894</pages><issn>1042-6507</issn><eissn>1563-5325</eissn><abstract>A series of 2-(substituteddithiocarbamoyl)-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide derivatives was designed and synthesized to combat the increasing incidence of drug-resistant fungal infections. All synthesized compounds were characterized by IR,
1
H-NMR,
13
C-NMR, and HRMS spectra and elemental analyses. Antifungal activity tests were performed against four different fungal strains. Molecular docking studies were performed to investigate the mode of action towards the fungal lanosterol 14α-demethylase, a cytochrome P450-dependent enzyme. ADME studies were carried out and a connection between activities and physicochemical properties of the target compounds was determined. Most of the final compounds exhibited significant activity against Candida albicans and Candida krusei with MIC
50
value 12.5 μg/mL. The results of in vitro anti-Candida activity, a docking study and ADME prediction revealed that the newly synthesized compounds have potential anti-Candida activity and evidenced the most active derivative, 5b (2-Pyrrolidinthiocarbonylthio-N-[4-((1H-imidazol-1-yl)methyl)phenyl]acetamide), which can be further optimized as a lead compound.</abstract><cop>Abingdon</cop><pub>Taylor & Francis</pub><doi>10.1080/10426507.2019.1565761</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-0151-6266</orcidid></addata></record> |
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source | Taylor and Francis Science and Technology Collection |
subjects | antifungal activity Antifungal agents Chemical synthesis Cytochromes P450 Derivatives dithiocarbamate Fungi Fungicides Imidazole Lead compounds Molecular docking NMR Nuclear magnetic resonance |
title | Novel imidazole derivatives as antifungal agents: Synthesis, biological evaluation, ADME prediction and molecular docking studies |
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