New imidazolidineiminothione derivatives: Synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities
A series of new imidazolidineiminothione derivatives with various halogenated and alkylated aromatic substituents at N-(1) and at N-(3) was synthesized through the reaction of N-arylcyanothioformamides with arylisocyanate derivatives. Structure of imidazolidineiminothione derivatives were establishe...
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Veröffentlicht in: | European journal of medicinal chemistry 2016-10, Vol.122, p.419-428 |
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creator | Moussa, Ziad El-Sharief, Marwa A.M.Sh Abbas, Samir Y. |
description | A series of new imidazolidineiminothione derivatives with various halogenated and alkylated aromatic substituents at N-(1) and at N-(3) was synthesized through the reaction of N-arylcyanothioformamides with arylisocyanate derivatives. Structure of imidazolidineiminothione derivatives were established based on spectroscopic IR, 1H NMR, 13C NMR, 1H,1H-COSY, HSQC, 19F NMR, MS and elemental analyses data. Evaluation of antitumor, antiviral, antibacterial and antifungal activities for the synthesized compounds were carried out to probe their activities. Most of the synthesized compounds displayed antitumor activity. The presence of 3,5-dichlorophenyl moiety at N-(1) and trichlorophenyl moiety on N-(3) (2f) resulted the highest cytotoxic activity. The presence of 9H-fluorenyl moiety on N-(3) resulted in the lowest cytotoxic activity. The antiviral screening displayed that 2d and 2f were markedly active against one or two viral strains. Compound 2d (3,5-dichlorophenyl moiety at N-(1) and 4-chlorophenyl moiety on N-(3)) showed 100% antiviral effect toward HAV. Compound 2f showed 96.7% antiviral effect toward HSV1 and 80.3% antiviral effect toward HAV. The antimicrobial activity suggested that all of the imidazolidineiminothione derivatives possess significant antimicrobial activity against most of the test organisms. Some imidazolidineiminothione derivatives showed MIC values of antibacterial and antifungal activities ranged from 0.78 to 6.25 μg/ml.
A series of new imidazolidineiminothiones with various substituents were synthesized. In vitro biological evaluation of such compounds showed significant antitumor, antiviral, antibacterial and antifungal activities. [Display omitted]
•Synthesis of N-arylcyanothioformamides derivatives.•Using the cyanothioformamides for synthesizing imidazolidineiminothiones.•Antitumor activity was determined.•Antiviral activity was determined.•Antibacterial and antifungal activities were determined. |
doi_str_mv | 10.1016/j.ejmech.2016.06.051 |
format | Article |
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A series of new imidazolidineiminothiones with various substituents were synthesized. In vitro biological evaluation of such compounds showed significant antitumor, antiviral, antibacterial and antifungal activities. [Display omitted]
•Synthesis of N-arylcyanothioformamides derivatives.•Using the cyanothioformamides for synthesizing imidazolidineiminothiones.•Antitumor activity was determined.•Antiviral activity was determined.•Antibacterial and antifungal activities were determined.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2016.06.051</identifier><identifier>PMID: 27393950</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial ; Antifungal activities ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antitumor ; Antiviral ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; Humans ; Imidazolidineiminothiones ; Imidazolidines - chemical synthesis ; Imidazolidines - chemistry ; Imidazolidines - pharmacology ; Microbial Sensitivity Tests ; N-Arylcyanothioformamides ; NMR spectra ; Structure-Activity Relationship</subject><ispartof>European journal of medicinal chemistry, 2016-10, Vol.122, p.419-428</ispartof><rights>2016 Elsevier Masson SAS</rights><rights>Copyright © 2016 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-3747f34c0442a2141ac9f69365e2d4da2a721a3e92c6a7cceac946d986c68cf93</citedby><cites>FETCH-LOGICAL-c362t-3747f34c0442a2141ac9f69365e2d4da2a721a3e92c6a7cceac946d986c68cf93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2016.06.051$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27393950$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Moussa, Ziad</creatorcontrib><creatorcontrib>El-Sharief, Marwa A.M.Sh</creatorcontrib><creatorcontrib>Abbas, Samir Y.</creatorcontrib><title>New imidazolidineiminothione derivatives: Synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A series of new imidazolidineiminothione derivatives with various halogenated and alkylated aromatic substituents at N-(1) and at N-(3) was synthesized through the reaction of N-arylcyanothioformamides with arylisocyanate derivatives. Structure of imidazolidineiminothione derivatives were established based on spectroscopic IR, 1H NMR, 13C NMR, 1H,1H-COSY, HSQC, 19F NMR, MS and elemental analyses data. Evaluation of antitumor, antiviral, antibacterial and antifungal activities for the synthesized compounds were carried out to probe their activities. Most of the synthesized compounds displayed antitumor activity. The presence of 3,5-dichlorophenyl moiety at N-(1) and trichlorophenyl moiety on N-(3) (2f) resulted the highest cytotoxic activity. The presence of 9H-fluorenyl moiety on N-(3) resulted in the lowest cytotoxic activity. The antiviral screening displayed that 2d and 2f were markedly active against one or two viral strains. Compound 2d (3,5-dichlorophenyl moiety at N-(1) and 4-chlorophenyl moiety on N-(3)) showed 100% antiviral effect toward HAV. Compound 2f showed 96.7% antiviral effect toward HSV1 and 80.3% antiviral effect toward HAV. The antimicrobial activity suggested that all of the imidazolidineiminothione derivatives possess significant antimicrobial activity against most of the test organisms. Some imidazolidineiminothione derivatives showed MIC values of antibacterial and antifungal activities ranged from 0.78 to 6.25 μg/ml.
A series of new imidazolidineiminothiones with various substituents were synthesized. In vitro biological evaluation of such compounds showed significant antitumor, antiviral, antibacterial and antifungal activities. [Display omitted]
•Synthesis of N-arylcyanothioformamides derivatives.•Using the cyanothioformamides for synthesizing imidazolidineiminothiones.•Antitumor activity was determined.•Antiviral activity was determined.•Antibacterial and antifungal activities were determined.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial</subject><subject>Antifungal activities</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antitumor</subject><subject>Antiviral</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Humans</subject><subject>Imidazolidineiminothiones</subject><subject>Imidazolidines - chemical synthesis</subject><subject>Imidazolidines - chemistry</subject><subject>Imidazolidines - pharmacology</subject><subject>Microbial Sensitivity Tests</subject><subject>N-Arylcyanothioformamides</subject><subject>NMR spectra</subject><subject>Structure-Activity Relationship</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU1v1DAQhi0EokvhHyCUI4dm8VecDQekquKjUtUegLPljiesV4m92E5Q-2P4rTik9Ig0kucdP--M7CHkNaNbRpl6d9jiYUTYb3lRW1qiYU_IhrVqVwveyKdkQzkXdcOFPCEvUjpQShtF6XNywlvRia6hG_L7Gn9VbnTW3IfBWeexCB_y3gWPlcXoZpPdjOl99fXO5z0ml86qdETI0QwV7E00kAt2X7DgK-NthbMZplWGvlSyy9MY4tnfdHbFt6a3q7O0WVxLpZ_8j0XCwmWH6SV51psh4auH85R8__Tx28WX-urm8-XF-VUNQvFci1a2vZBApeSGM8kMdL3qhGqQW2kNNy1nRmDHQZkWAMu9VLbbKVA76DtxSt6ufY8x_JwwZT26BDgMxmOYkmY71gjVMiUKKlcUYkgpYq-P0Y0m3mlG9bIZfdDrZvSyGU1LNKzY3jxMmG5HtI-mf6sowIcVwPLO2WHUCRx6QOti-W1tg_v_hD_MX6ZK</recordid><startdate>20161021</startdate><enddate>20161021</enddate><creator>Moussa, Ziad</creator><creator>El-Sharief, Marwa A.M.Sh</creator><creator>Abbas, Samir Y.</creator><general>Elsevier Masson SAS</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>7X8</scope></search><sort><creationdate>20161021</creationdate><title>New imidazolidineiminothione derivatives: Synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities</title><author>Moussa, Ziad ; El-Sharief, Marwa A.M.Sh ; Abbas, Samir Y.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-3747f34c0442a2141ac9f69365e2d4da2a721a3e92c6a7cceac946d986c68cf93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial</topic><topic>Antifungal activities</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antitumor</topic><topic>Antiviral</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Imidazolidineiminothiones</topic><topic>Imidazolidines - chemical synthesis</topic><topic>Imidazolidines - chemistry</topic><topic>Imidazolidines - pharmacology</topic><topic>Microbial Sensitivity Tests</topic><topic>N-Arylcyanothioformamides</topic><topic>NMR spectra</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moussa, Ziad</creatorcontrib><creatorcontrib>El-Sharief, Marwa A.M.Sh</creatorcontrib><creatorcontrib>Abbas, Samir Y.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moussa, Ziad</au><au>El-Sharief, Marwa A.M.Sh</au><au>Abbas, Samir Y.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New imidazolidineiminothione derivatives: Synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2016-10-21</date><risdate>2016</risdate><volume>122</volume><spage>419</spage><epage>428</epage><pages>419-428</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>A series of new imidazolidineiminothione derivatives with various halogenated and alkylated aromatic substituents at N-(1) and at N-(3) was synthesized through the reaction of N-arylcyanothioformamides with arylisocyanate derivatives. Structure of imidazolidineiminothione derivatives were established based on spectroscopic IR, 1H NMR, 13C NMR, 1H,1H-COSY, HSQC, 19F NMR, MS and elemental analyses data. Evaluation of antitumor, antiviral, antibacterial and antifungal activities for the synthesized compounds were carried out to probe their activities. Most of the synthesized compounds displayed antitumor activity. The presence of 3,5-dichlorophenyl moiety at N-(1) and trichlorophenyl moiety on N-(3) (2f) resulted the highest cytotoxic activity. The presence of 9H-fluorenyl moiety on N-(3) resulted in the lowest cytotoxic activity. The antiviral screening displayed that 2d and 2f were markedly active against one or two viral strains. Compound 2d (3,5-dichlorophenyl moiety at N-(1) and 4-chlorophenyl moiety on N-(3)) showed 100% antiviral effect toward HAV. Compound 2f showed 96.7% antiviral effect toward HSV1 and 80.3% antiviral effect toward HAV. The antimicrobial activity suggested that all of the imidazolidineiminothione derivatives possess significant antimicrobial activity against most of the test organisms. Some imidazolidineiminothione derivatives showed MIC values of antibacterial and antifungal activities ranged from 0.78 to 6.25 μg/ml.
A series of new imidazolidineiminothiones with various substituents were synthesized. In vitro biological evaluation of such compounds showed significant antitumor, antiviral, antibacterial and antifungal activities. [Display omitted]
•Synthesis of N-arylcyanothioformamides derivatives.•Using the cyanothioformamides for synthesizing imidazolidineiminothiones.•Antitumor activity was determined.•Antiviral activity was determined.•Antibacterial and antifungal activities were determined.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>27393950</pmid><doi>10.1016/j.ejmech.2016.06.051</doi><tpages>10</tpages></addata></record> |
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subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial Antifungal activities Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antitumor Antiviral Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Cell Line, Tumor Drug Screening Assays, Antitumor Humans Imidazolidineiminothiones Imidazolidines - chemical synthesis Imidazolidines - chemistry Imidazolidines - pharmacology Microbial Sensitivity Tests N-Arylcyanothioformamides NMR spectra Structure-Activity Relationship |
title | New imidazolidineiminothione derivatives: Synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities |
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