Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones
A new series of 2-thiazolylimino-5-arylidene-4-thiazolidinones were synthesized and assayed in vitro for their antimicrobial activity. The designed compounds exhibited a remarkable inhibition of the growth of a wide number of Gram positive bacteria, including penicillin resistant strains, and of Gra...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2006-06, Vol.14 (11), p.3859-3864 |
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| creator | Vicini, Paola Geronikaki, Athina Anastasia, Kitka Incerti, Matteo Zani, Franca |
| description | A new series of 2-thiazolylimino-5-arylidene-4-thiazolidinones were synthesized and assayed in vitro for their antimicrobial activity. The designed compounds exhibited a remarkable inhibition of the growth of a wide number of Gram positive bacteria, including penicillin resistant strains, and of Gram negative
Haemophilus influenzae.
New 2-thiazolylimino-5-arylidene-4-thiazolidinones (compounds
4a–
j), unsubstituted or carrying hydroxy, methoxy, nitro and chloro groups on the benzene ring, were synthesized and assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria, yeasts and mould. The compounds were very potent towards all tested Gram positive microorganisms (MIC ranging from 0.03 to 6
μg/mL in most of the cases) and Gram negative
Haemophilus influenzae (MIC 0.15–1.5
μg/mL), whereas no effectiveness was exhibited against Gram negative
Escherichia coli and fungi up to the concentration of 100
μg/mL. The 5-arylidene derivatives showed an antibacterial efficacy considerably greater than that of the parent 2-(thiazol-2-ylimino)thiazolidin-4-one
3, suggesting that the substituted and unsubstituted 5-arylidene moiety plays an important role in enhancing the antimicrobial properties of this class of compounds. The remarkable inhibition of the growth of penicillin-resistant staphylococci makes these substances promising agents also for the treatment of infections caused by microorganisms resistant to currently available drugs. |
| doi_str_mv | 10.1016/j.bmc.2006.01.043 |
| format | Article |
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Haemophilus influenzae.
New 2-thiazolylimino-5-arylidene-4-thiazolidinones (compounds
4a–
j), unsubstituted or carrying hydroxy, methoxy, nitro and chloro groups on the benzene ring, were synthesized and assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria, yeasts and mould. The compounds were very potent towards all tested Gram positive microorganisms (MIC ranging from 0.03 to 6
μg/mL in most of the cases) and Gram negative
Haemophilus influenzae (MIC 0.15–1.5
μg/mL), whereas no effectiveness was exhibited against Gram negative
Escherichia coli and fungi up to the concentration of 100
μg/mL. The 5-arylidene derivatives showed an antibacterial efficacy considerably greater than that of the parent 2-(thiazol-2-ylimino)thiazolidin-4-one
3, suggesting that the substituted and unsubstituted 5-arylidene moiety plays an important role in enhancing the antimicrobial properties of this class of compounds. The remarkable inhibition of the growth of penicillin-resistant staphylococci makes these substances promising agents also for the treatment of infections caused by microorganisms resistant to currently available drugs.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2006.01.043</identifier><identifier>PMID: 16488614</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>2-Thiazolylimino-5-arylidene-4-thiazolidinones ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antifungal agents ; Antimicrobial activity ; Biological and medical sciences ; Escherichia coli ; General aspects ; Gram-Negative Bacteria - drug effects ; Gram-Positive Bacteria - drug effects ; Haemophilus influenzae ; Medical sciences ; Microbial Sensitivity Tests ; Molecular Structure ; Pharmacology. Drug treatments ; Structure-Activity Relationship ; Thiazole derivatives ; Thiazoles - chemical synthesis ; Thiazoles - chemistry ; Thiazoles - pharmacology ; Thiazolidinone derivatives</subject><ispartof>Bioorganic & medicinal chemistry, 2006-06, Vol.14 (11), p.3859-3864</ispartof><rights>2006 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c478t-9b5c7c25145094ac09ca305f9f33ad75d2d7f57ce25e28a38534504c6402b3953</citedby><cites>FETCH-LOGICAL-c478t-9b5c7c25145094ac09ca305f9f33ad75d2d7f57ce25e28a38534504c6402b3953</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089606000745$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17698201$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16488614$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vicini, Paola</creatorcontrib><creatorcontrib>Geronikaki, Athina</creatorcontrib><creatorcontrib>Anastasia, Kitka</creatorcontrib><creatorcontrib>Incerti, Matteo</creatorcontrib><creatorcontrib>Zani, Franca</creatorcontrib><title>Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A new series of 2-thiazolylimino-5-arylidene-4-thiazolidinones were synthesized and assayed in vitro for their antimicrobial activity. The designed compounds exhibited a remarkable inhibition of the growth of a wide number of Gram positive bacteria, including penicillin resistant strains, and of Gram negative
Haemophilus influenzae.
New 2-thiazolylimino-5-arylidene-4-thiazolidinones (compounds
4a–
j), unsubstituted or carrying hydroxy, methoxy, nitro and chloro groups on the benzene ring, were synthesized and assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria, yeasts and mould. The compounds were very potent towards all tested Gram positive microorganisms (MIC ranging from 0.03 to 6
μg/mL in most of the cases) and Gram negative
Haemophilus influenzae (MIC 0.15–1.5
μg/mL), whereas no effectiveness was exhibited against Gram negative
Escherichia coli and fungi up to the concentration of 100
μg/mL. The 5-arylidene derivatives showed an antibacterial efficacy considerably greater than that of the parent 2-(thiazol-2-ylimino)thiazolidin-4-one
3, suggesting that the substituted and unsubstituted 5-arylidene moiety plays an important role in enhancing the antimicrobial properties of this class of compounds. The remarkable inhibition of the growth of penicillin-resistant staphylococci makes these substances promising agents also for the treatment of infections caused by microorganisms resistant to currently available drugs.</description><subject>2-Thiazolylimino-5-arylidene-4-thiazolidinones</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal agents</subject><subject>Antimicrobial activity</subject><subject>Biological and medical sciences</subject><subject>Escherichia coli</subject><subject>General aspects</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Haemophilus influenzae</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><subject>Thiazole derivatives</subject><subject>Thiazoles - chemical synthesis</subject><subject>Thiazoles - chemistry</subject><subject>Thiazoles - pharmacology</subject><subject>Thiazolidinone derivatives</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEuLFDEQgIMo7rj6A7xIX_SW3sqzEzzJ4gsW9uDuTQjppJrN0J1eOz0D4683w4zsTQ9FFdRXRdVHyFsGLQOmr7ZtP4WWA-gWWAtSPCMbJrWkQlj2nGzAakPBWH1BXpWyBQAuLXtJLpiWxmgmN-Tnj0NeH7Ck0vgca6xpSmGZ--THxoc17dN6aOahyfMex4bT9SH53_N4GCuXZ6qoX2odMSOVf5sp1lbG8pq8GPxY8M05X5L7L5_vrr_Rm9uv368_3dAgO7NS26vQBa6YVGClD2CDF6AGOwjhY6cij92guoBcITdeGCUqKYOWwHthlbgkH057H5f51w7L6qZUAo6jzzjvitOdMZZL81-Q2a7jzBxBdgKrilIWHNzjkqb6qmPgju7d1lX37ujeAXPVfZ15d16-6yeMTxNn2RV4fwZ8CX4cFp9DKk9cp63hwCr38cRhdbZPuLgSEuaAMS0YVhfn9I8z_gCyKqFo</recordid><startdate>20060601</startdate><enddate>20060601</enddate><creator>Vicini, Paola</creator><creator>Geronikaki, Athina</creator><creator>Anastasia, Kitka</creator><creator>Incerti, Matteo</creator><creator>Zani, Franca</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</scope><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>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20060601</creationdate><title>Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones</title><author>Vicini, Paola ; Geronikaki, Athina ; Anastasia, Kitka ; Incerti, Matteo ; Zani, Franca</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c478t-9b5c7c25145094ac09ca305f9f33ad75d2d7f57ce25e28a38534504c6402b3953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>2-Thiazolylimino-5-arylidene-4-thiazolidinones</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antifungal agents</topic><topic>Antimicrobial activity</topic><topic>Biological and medical sciences</topic><topic>Escherichia coli</topic><topic>General aspects</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Haemophilus influenzae</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><topic>Thiazole derivatives</topic><topic>Thiazoles - chemical synthesis</topic><topic>Thiazoles - chemistry</topic><topic>Thiazoles - pharmacology</topic><topic>Thiazolidinone derivatives</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vicini, Paola</creatorcontrib><creatorcontrib>Geronikaki, Athina</creatorcontrib><creatorcontrib>Anastasia, Kitka</creatorcontrib><creatorcontrib>Incerti, Matteo</creatorcontrib><creatorcontrib>Zani, Franca</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vicini, Paola</au><au>Geronikaki, Athina</au><au>Anastasia, Kitka</au><au>Incerti, Matteo</au><au>Zani, Franca</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2006-06-01</date><risdate>2006</risdate><volume>14</volume><issue>11</issue><spage>3859</spage><epage>3864</epage><pages>3859-3864</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A new series of 2-thiazolylimino-5-arylidene-4-thiazolidinones were synthesized and assayed in vitro for their antimicrobial activity. The designed compounds exhibited a remarkable inhibition of the growth of a wide number of Gram positive bacteria, including penicillin resistant strains, and of Gram negative
Haemophilus influenzae.
New 2-thiazolylimino-5-arylidene-4-thiazolidinones (compounds
4a–
j), unsubstituted or carrying hydroxy, methoxy, nitro and chloro groups on the benzene ring, were synthesized and assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria, yeasts and mould. The compounds were very potent towards all tested Gram positive microorganisms (MIC ranging from 0.03 to 6
μg/mL in most of the cases) and Gram negative
Haemophilus influenzae (MIC 0.15–1.5
μg/mL), whereas no effectiveness was exhibited against Gram negative
Escherichia coli and fungi up to the concentration of 100
μg/mL. The 5-arylidene derivatives showed an antibacterial efficacy considerably greater than that of the parent 2-(thiazol-2-ylimino)thiazolidin-4-one
3, suggesting that the substituted and unsubstituted 5-arylidene moiety plays an important role in enhancing the antimicrobial properties of this class of compounds. The remarkable inhibition of the growth of penicillin-resistant staphylococci makes these substances promising agents also for the treatment of infections caused by microorganisms resistant to currently available drugs.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16488614</pmid><doi>10.1016/j.bmc.2006.01.043</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2006-06, Vol.14 (11), p.3859-3864 |
| issn | 0968-0896 1464-3391 |
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| source | MEDLINE; Elsevier ScienceDirect Journals Collection |
| subjects | 2-Thiazolylimino-5-arylidene-4-thiazolidinones Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antimicrobial activity Biological and medical sciences Escherichia coli General aspects Gram-Negative Bacteria - drug effects Gram-Positive Bacteria - drug effects Haemophilus influenzae Medical sciences Microbial Sensitivity Tests Molecular Structure Pharmacology. Drug treatments Structure-Activity Relationship Thiazole derivatives Thiazoles - chemical synthesis Thiazoles - chemistry Thiazoles - pharmacology Thiazolidinone derivatives |
| title | Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones |
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