N-Acylated and N, N′-diacylated imidazolidine-2-thione derivatives and N, N′-diacylated tetrahydropyrimidine-2(1 H)-thione analogues: Synthesis and antiproliferative activity
Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs 1o (3,5-dichlorobenzoyl), 1s (2-furoyl), 3s (2-furoyl) and 1t (2-the...
Gespeichert in:
| Veröffentlicht in: | European journal of medicinal chemistry 2009-03, Vol.44 (3), p.1106-1118 |
|---|---|
| Hauptverfasser: | , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1118 |
|---|---|
| container_issue | 3 |
| container_start_page | 1106 |
| container_title | European journal of medicinal chemistry |
| container_volume | 44 |
| creator | Cesarini, Sara Spallarossa, Andrea Ranise, Angelo Schenone, Silvia Rosano, Camillo La Colla, Paolo Sanna, Giuseppina Busonera, Bernardetta Loddo, Roberta |
| description | Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs
1o (3,5-dichlorobenzoyl),
1s (2-furoyl),
3s (2-furoyl) and
1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3–9.7
μM concentration range. Compound
14s exhibited selectivity for melanoma SK-MEL-5 (GI
50
<
5
nM);
1s for leukemia MOLT-4 (GI
50: 300
nM);
1q,
3b and
3q for renal cancer UO-31 (GI
50: 70–200
nM);
8s,
9s for non-small cell lung cancer EKVX (GI
50: 300, 10
nM) and
3j for HOP-92 (GI
50: 700
nM) cell line.
[Display omitted] |
| doi_str_mv | 10.1016/j.ejmech.2008.06.010 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_66980370</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0223523408003115</els_id><sourcerecordid>66980370</sourcerecordid><originalsourceid>FETCH-LOGICAL-c390t-382b7bdda379bf3017941df40fcd48e2020b38899fb0c8aa0a6fa708dc674d203</originalsourceid><addsrcrecordid>eNp9kcFu1DAQhi0EotvCGyCUC6hIZBk7ieNwQKoqoEjVcgDO1sSesF5lk63tXSmceKY-Ek9C0mzhBKeRrP__5h__jD3jsOTA5ZvNkjZbMuulAFBLkEvg8IAteClVmokif8gWIESWFiLLT9hpCBsAKCTAY3bClZSlKKoFu12lF2ZoMZJNsLPJ6nWy-vXzNrUO75_d1ln80bfOuo5Skca16ztKLHl3wOgOFP7ljBQ9rgfr-93gJ8wd4JwnV6_uKdhh23_fU3ibfBm6uKbgZhx20e38uLUhf7clQTMOF4cn7FGDbaCnx3nGvn14__XyKr3-_PHT5cV1arIKYpopUZe1tZiVVd1kwMsq57bJoTE2VyRAQJ0pVVVNDUYhAsoGS1DWyDK3ArIz9nLmjjFuxoRRb10w1LbYUb8PWspKQVZOwnwWGt-H4KnRu_Fa9IPmoKeu9EbPXempKw1Sj12NtudH_r7ekv1rOpYzCl4cBRgMto3HzrjwRye4kEVZTaB3s47G3zg48joYR50h6zyZqG3v_p_kN4j6uP0</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>66980370</pqid></control><display><type>article</type><title>N-Acylated and N, N′-diacylated imidazolidine-2-thione derivatives and N, N′-diacylated tetrahydropyrimidine-2(1 H)-thione analogues: Synthesis and antiproliferative activity</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>Cesarini, Sara ; Spallarossa, Andrea ; Ranise, Angelo ; Schenone, Silvia ; Rosano, Camillo ; La Colla, Paolo ; Sanna, Giuseppina ; Busonera, Bernardetta ; Loddo, Roberta</creator><creatorcontrib>Cesarini, Sara ; Spallarossa, Andrea ; Ranise, Angelo ; Schenone, Silvia ; Rosano, Camillo ; La Colla, Paolo ; Sanna, Giuseppina ; Busonera, Bernardetta ; Loddo, Roberta</creatorcontrib><description>Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs
1o (3,5-dichlorobenzoyl),
1s (2-furoyl),
3s (2-furoyl) and
1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3–9.7
μM concentration range. Compound
14s exhibited selectivity for melanoma SK-MEL-5 (GI
50
<
5
nM);
1s for leukemia MOLT-4 (GI
50: 300
nM);
1q,
3b and
3q for renal cancer UO-31 (GI
50: 70–200
nM);
8s,
9s for non-small cell lung cancer EKVX (GI
50: 300, 10
nM) and
3j for HOP-92 (GI
50: 700
nM) cell line.
[Display omitted]</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2008.06.010</identifier><identifier>PMID: 18667259</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Acylation ; Acylthioureas ; Antineoplastic agents ; Antiproliferative activity ; Biological and medical sciences ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; Imidazolidines - chemical synthesis ; Imidazolidines - pharmacology ; Magnetic Resonance Spectroscopy ; Medical sciences ; Parallel synthesis ; Pharmacology. Drug treatments ; Pyrimidines - chemical synthesis ; Pyrimidines - pharmacology ; Spectrophotometry, Infrared</subject><ispartof>European journal of medicinal chemistry, 2009-03, Vol.44 (3), p.1106-1118</ispartof><rights>2008 Elsevier Masson SAS</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-382b7bdda379bf3017941df40fcd48e2020b38899fb0c8aa0a6fa708dc674d203</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523408003115$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21265790$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18667259$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cesarini, Sara</creatorcontrib><creatorcontrib>Spallarossa, Andrea</creatorcontrib><creatorcontrib>Ranise, Angelo</creatorcontrib><creatorcontrib>Schenone, Silvia</creatorcontrib><creatorcontrib>Rosano, Camillo</creatorcontrib><creatorcontrib>La Colla, Paolo</creatorcontrib><creatorcontrib>Sanna, Giuseppina</creatorcontrib><creatorcontrib>Busonera, Bernardetta</creatorcontrib><creatorcontrib>Loddo, Roberta</creatorcontrib><title>N-Acylated and N, N′-diacylated imidazolidine-2-thione derivatives and N, N′-diacylated tetrahydropyrimidine-2(1 H)-thione analogues: Synthesis and antiproliferative activity</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs
1o (3,5-dichlorobenzoyl),
1s (2-furoyl),
3s (2-furoyl) and
1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3–9.7
μM concentration range. Compound
14s exhibited selectivity for melanoma SK-MEL-5 (GI
50
<
5
nM);
1s for leukemia MOLT-4 (GI
50: 300
nM);
1q,
3b and
3q for renal cancer UO-31 (GI
50: 70–200
nM);
8s,
9s for non-small cell lung cancer EKVX (GI
50: 300, 10
nM) and
3j for HOP-92 (GI
50: 700
nM) cell line.
[Display omitted]</description><subject>Acylation</subject><subject>Acylthioureas</subject><subject>Antineoplastic agents</subject><subject>Antiproliferative activity</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>Imidazolidines - chemical synthesis</subject><subject>Imidazolidines - pharmacology</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Parallel synthesis</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - pharmacology</subject><subject>Spectrophotometry, Infrared</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcFu1DAQhi0EotvCGyCUC6hIZBk7ieNwQKoqoEjVcgDO1sSesF5lk63tXSmceKY-Ek9C0mzhBKeRrP__5h__jD3jsOTA5ZvNkjZbMuulAFBLkEvg8IAteClVmokif8gWIESWFiLLT9hpCBsAKCTAY3bClZSlKKoFu12lF2ZoMZJNsLPJ6nWy-vXzNrUO75_d1ln80bfOuo5Skca16ztKLHl3wOgOFP7ljBQ9rgfr-93gJ8wd4JwnV6_uKdhh23_fU3ibfBm6uKbgZhx20e38uLUhf7clQTMOF4cn7FGDbaCnx3nGvn14__XyKr3-_PHT5cV1arIKYpopUZe1tZiVVd1kwMsq57bJoTE2VyRAQJ0pVVVNDUYhAsoGS1DWyDK3ArIz9nLmjjFuxoRRb10w1LbYUb8PWspKQVZOwnwWGt-H4KnRu_Fa9IPmoKeu9EbPXempKw1Sj12NtudH_r7ekv1rOpYzCl4cBRgMto3HzrjwRye4kEVZTaB3s47G3zg48joYR50h6zyZqG3v_p_kN4j6uP0</recordid><startdate>20090301</startdate><enddate>20090301</enddate><creator>Cesarini, Sara</creator><creator>Spallarossa, Andrea</creator><creator>Ranise, Angelo</creator><creator>Schenone, Silvia</creator><creator>Rosano, Camillo</creator><creator>La Colla, Paolo</creator><creator>Sanna, Giuseppina</creator><creator>Busonera, Bernardetta</creator><creator>Loddo, Roberta</creator><general>Elsevier Masson SAS</general><general>Elsevier</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>7X8</scope></search><sort><creationdate>20090301</creationdate><title>N-Acylated and N, N′-diacylated imidazolidine-2-thione derivatives and N, N′-diacylated tetrahydropyrimidine-2(1 H)-thione analogues: Synthesis and antiproliferative activity</title><author>Cesarini, Sara ; Spallarossa, Andrea ; Ranise, Angelo ; Schenone, Silvia ; Rosano, Camillo ; La Colla, Paolo ; Sanna, Giuseppina ; Busonera, Bernardetta ; Loddo, Roberta</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-382b7bdda379bf3017941df40fcd48e2020b38899fb0c8aa0a6fa708dc674d203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Acylation</topic><topic>Acylthioureas</topic><topic>Antineoplastic agents</topic><topic>Antiproliferative activity</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>Imidazolidines - chemical synthesis</topic><topic>Imidazolidines - pharmacology</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Parallel synthesis</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - pharmacology</topic><topic>Spectrophotometry, Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cesarini, Sara</creatorcontrib><creatorcontrib>Spallarossa, Andrea</creatorcontrib><creatorcontrib>Ranise, Angelo</creatorcontrib><creatorcontrib>Schenone, Silvia</creatorcontrib><creatorcontrib>Rosano, Camillo</creatorcontrib><creatorcontrib>La Colla, Paolo</creatorcontrib><creatorcontrib>Sanna, Giuseppina</creatorcontrib><creatorcontrib>Busonera, Bernardetta</creatorcontrib><creatorcontrib>Loddo, Roberta</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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cesarini, Sara</au><au>Spallarossa, Andrea</au><au>Ranise, Angelo</au><au>Schenone, Silvia</au><au>Rosano, Camillo</au><au>La Colla, Paolo</au><au>Sanna, Giuseppina</au><au>Busonera, Bernardetta</au><au>Loddo, Roberta</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N-Acylated and N, N′-diacylated imidazolidine-2-thione derivatives and N, N′-diacylated tetrahydropyrimidine-2(1 H)-thione analogues: Synthesis and antiproliferative activity</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2009-03-01</date><risdate>2009</risdate><volume>44</volume><issue>3</issue><spage>1106</spage><epage>1118</epage><pages>1106-1118</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Fifty-one acylthioureas (ATUs) incorporating imidazolidine-2-thione or its upper cyclohomologue were prepared by parallel synthesis and evaluated against a high number of human cancer cell lines for antiproliferative activity. ATUs
1o (3,5-dichlorobenzoyl),
1s (2-furoyl),
3s (2-furoyl) and
1t (2-thenoyl) displayed activity against leukemia, melanoma LOX IMVI, non-small cell lung NCI-H522, renal 786-0, CAKI-1, SN12C, UO-31 and breast MCF7, MDA-MB-435, T-47D cancer cell lines in the 0.3–9.7
μM concentration range. Compound
14s exhibited selectivity for melanoma SK-MEL-5 (GI
50
<
5
nM);
1s for leukemia MOLT-4 (GI
50: 300
nM);
1q,
3b and
3q for renal cancer UO-31 (GI
50: 70–200
nM);
8s,
9s for non-small cell lung cancer EKVX (GI
50: 300, 10
nM) and
3j for HOP-92 (GI
50: 700
nM) cell line.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>18667259</pmid><doi>10.1016/j.ejmech.2008.06.010</doi><tpages>13</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2009-03, Vol.44 (3), p.1106-1118 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_66980370 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Acylation Acylthioureas Antineoplastic agents Antiproliferative activity Biological and medical sciences Cell Line, Tumor Cell Proliferation - drug effects Drug Screening Assays, Antitumor General aspects Humans Imidazolidines - chemical synthesis Imidazolidines - pharmacology Magnetic Resonance Spectroscopy Medical sciences Parallel synthesis Pharmacology. Drug treatments Pyrimidines - chemical synthesis Pyrimidines - pharmacology Spectrophotometry, Infrared |
| title | N-Acylated and N, N′-diacylated imidazolidine-2-thione derivatives and N, N′-diacylated tetrahydropyrimidine-2(1 H)-thione analogues: Synthesis and antiproliferative activity |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-25T02%3A40%3A57IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=N-Acylated%20and%20N,%20N%E2%80%B2-diacylated%20imidazolidine-2-thione%20derivatives%20and%20N,%20N%E2%80%B2-diacylated%20tetrahydropyrimidine-2(1%20H)-thione%20analogues:%20Synthesis%20and%20antiproliferative%20activity&rft.jtitle=European%20journal%20of%20medicinal%20chemistry&rft.au=Cesarini,%20Sara&rft.date=2009-03-01&rft.volume=44&rft.issue=3&rft.spage=1106&rft.epage=1118&rft.pages=1106-1118&rft.issn=0223-5234&rft.eissn=1768-3254&rft.coden=EJMCA5&rft_id=info:doi/10.1016/j.ejmech.2008.06.010&rft_dat=%3Cproquest_cross%3E66980370%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=66980370&rft_id=info:pmid/18667259&rft_els_id=S0223523408003115&rfr_iscdi=true |