Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids
This work is part of a large program, which seeks to discover new antitumor isobenfuranones designed from anacardic acids. The synthetic strategy for the construction of the title compounds takes into consideration the use of inexpensive anacardic acids ( 2), the major natural cashew ( Anacardium oc...
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| Veröffentlicht in: | European journal of medicinal chemistry 2010-08, Vol.45 (8), p.3480-3489 |
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| creator | Logrado, Lúcio P.L. Santos, Camila O. Romeiro, Luiz A.S. Costa, Arinice M. Ferreira, José R.O. Cavalcanti, Bruno C. Manoel de Moraes, O. Costa-Lotufo, Letícia V. Pessoa, Cláudia dos Santos, Maria L. |
| description | This work is part of a large program, which seeks to discover new antitumor isobenfuranones designed from anacardic acids. The synthetic strategy for the construction of the title compounds takes into consideration the use of inexpensive anacardic acids (
2), the major natural cashew (
Anacardium occidentale) nut-shell phenolic lipid, and features one-pot construction of fused-ring aromatic γ-lactones, phthalides. The cytotoxicity screening in different human cancer cell lines (HL-60 leukemia, SF295 glioblastoma and MDA-MB435 melanoma) by the MTT assay showed that acyclic precursor (
6), and isobenfuranones (
1a and
1b) are active compounds. Interestingly,
1a exhibits significant antiproliferative effect against HL-60 cells and moderate activity against SF295 and MDA-MB435 cell lines. Analysis of mechanisms involved in the cytotoxic activity showed that active compounds were leading to DNA damage, triggering apoptosis or necrosis induction.
A simple approach to isobenzofuranones from anacardic acids is described. Compound (
1b) showed a discriminatory antiproliferative effects against HL-60 cells.
[Display omitted] |
| doi_str_mv | 10.1016/j.ejmech.2010.05.015 |
| format | Article |
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2), the major natural cashew (
Anacardium occidentale) nut-shell phenolic lipid, and features one-pot construction of fused-ring aromatic γ-lactones, phthalides. The cytotoxicity screening in different human cancer cell lines (HL-60 leukemia, SF295 glioblastoma and MDA-MB435 melanoma) by the MTT assay showed that acyclic precursor (
6), and isobenfuranones (
1a and
1b) are active compounds. Interestingly,
1a exhibits significant antiproliferative effect against HL-60 cells and moderate activity against SF295 and MDA-MB435 cell lines. Analysis of mechanisms involved in the cytotoxic activity showed that active compounds were leading to DNA damage, triggering apoptosis or necrosis induction.
A simple approach to isobenzofuranones from anacardic acids is described. Compound (
1b) showed a discriminatory antiproliferative effects against HL-60 cells.
[Display omitted]</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2010.05.015</identifier><identifier>PMID: 20537433</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Anacardic acids ; Anacardic Acids - chemistry ; Animals ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Apoptosis - drug effects ; Benzofurans - chemical synthesis ; Benzofurans - chemistry ; Benzofurans - pharmacology ; Biological and medical sciences ; Cell Line, Tumor ; Cell Proliferation - drug effects ; Cell Survival - drug effects ; Cytotoxicity screening ; Drug Design ; Drug Evaluation, Preclinical - methods ; General aspects ; Humans ; Hydrophobic and Hydrophilic Interactions ; Inhibitory Concentration 50 ; Isobenzofuranones ; Medical sciences ; Oxygen - chemistry ; Pharmacology. Drug treatments ; Phthalides</subject><ispartof>European journal of medicinal chemistry, 2010-08, Vol.45 (8), p.3480-3489</ispartof><rights>2010 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><rights>Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-4b463b137d4e398a6106b577f0d0677922cec3c1339597faec8fa56f9a2858f03</citedby><cites>FETCH-LOGICAL-c457t-4b463b137d4e398a6106b577f0d0677922cec3c1339597faec8fa56f9a2858f03</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.2010.05.015$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22984930$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20537433$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Logrado, Lúcio P.L.</creatorcontrib><creatorcontrib>Santos, Camila O.</creatorcontrib><creatorcontrib>Romeiro, Luiz A.S.</creatorcontrib><creatorcontrib>Costa, Arinice M.</creatorcontrib><creatorcontrib>Ferreira, José R.O.</creatorcontrib><creatorcontrib>Cavalcanti, Bruno C.</creatorcontrib><creatorcontrib>Manoel de Moraes, O.</creatorcontrib><creatorcontrib>Costa-Lotufo, Letícia V.</creatorcontrib><creatorcontrib>Pessoa, Cláudia</creatorcontrib><creatorcontrib>dos Santos, Maria L.</creatorcontrib><title>Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>This work is part of a large program, which seeks to discover new antitumor isobenfuranones designed from anacardic acids. The synthetic strategy for the construction of the title compounds takes into consideration the use of inexpensive anacardic acids (
2), the major natural cashew (
Anacardium occidentale) nut-shell phenolic lipid, and features one-pot construction of fused-ring aromatic γ-lactones, phthalides. The cytotoxicity screening in different human cancer cell lines (HL-60 leukemia, SF295 glioblastoma and MDA-MB435 melanoma) by the MTT assay showed that acyclic precursor (
6), and isobenfuranones (
1a and
1b) are active compounds. Interestingly,
1a exhibits significant antiproliferative effect against HL-60 cells and moderate activity against SF295 and MDA-MB435 cell lines. Analysis of mechanisms involved in the cytotoxic activity showed that active compounds were leading to DNA damage, triggering apoptosis or necrosis induction.
A simple approach to isobenzofuranones from anacardic acids is described. Compound (
1b) showed a discriminatory antiproliferative effects against HL-60 cells.
[Display omitted]</description><subject>Anacardic acids</subject><subject>Anacardic Acids - chemistry</subject><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis - drug effects</subject><subject>Benzofurans - chemical synthesis</subject><subject>Benzofurans - chemistry</subject><subject>Benzofurans - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>Cell Survival - drug effects</subject><subject>Cytotoxicity screening</subject><subject>Drug Design</subject><subject>Drug Evaluation, Preclinical - methods</subject><subject>General aspects</subject><subject>Humans</subject><subject>Hydrophobic and Hydrophilic Interactions</subject><subject>Inhibitory Concentration 50</subject><subject>Isobenzofuranones</subject><subject>Medical sciences</subject><subject>Oxygen - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Phthalides</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMGKFDEQhoMo7rj6BiJ9EU89ppNOp_siyKKusOBBPYd0pbKbYTpZU-nF8enNMKPezKUg9dVfxcfYy45vO94Nb3db3C0Id1vB6xdXW96pR2zT6WFspVD9Y7bhQshWCdlfsGdEO865Gjh_yi4EV1L3Um4YfD3EcocUqLHRNXAoqaSfAUI5NAQZMYZ42yTf0DpTCWUt6JpAacb4K_k125giUuNqwm2sLZ_TUpMs2OwCNBaCo-fsibd7whfnesm-f_zw7eq6vfny6fPV-5sWeqVL28_9IOdOatejnEY7dHyYldaeOz5oPQkBCBI6KSc1aW8RRm_V4CcrRjV6Li_Zm1PufU4_VqRilkCA-72NmFYyWtY3THKsZH8iISeijN7c57DYfDAdN0e7ZmdOds3RruHKVLt17NV5wTov6P4O_dFZgddnwBLYva96INA_TkxjP8njpe9OHFYdDwGzIQgYAV3ICMW4FP5_yW9tn5uU</recordid><startdate>20100801</startdate><enddate>20100801</enddate><creator>Logrado, Lúcio P.L.</creator><creator>Santos, Camila O.</creator><creator>Romeiro, Luiz A.S.</creator><creator>Costa, Arinice M.</creator><creator>Ferreira, José R.O.</creator><creator>Cavalcanti, Bruno C.</creator><creator>Manoel de Moraes, O.</creator><creator>Costa-Lotufo, Letícia V.</creator><creator>Pessoa, Cláudia</creator><creator>dos Santos, Maria L.</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>20100801</creationdate><title>Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids</title><author>Logrado, Lúcio P.L. ; Santos, Camila O. ; Romeiro, Luiz A.S. ; Costa, Arinice M. ; Ferreira, José R.O. ; Cavalcanti, Bruno C. ; Manoel de Moraes, O. ; Costa-Lotufo, Letícia V. ; Pessoa, Cláudia ; dos Santos, Maria L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-4b463b137d4e398a6106b577f0d0677922cec3c1339597faec8fa56f9a2858f03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Anacardic acids</topic><topic>Anacardic Acids - chemistry</topic><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis - drug effects</topic><topic>Benzofurans - chemical synthesis</topic><topic>Benzofurans - chemistry</topic><topic>Benzofurans - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>Cell Survival - drug effects</topic><topic>Cytotoxicity screening</topic><topic>Drug Design</topic><topic>Drug Evaluation, Preclinical - methods</topic><topic>General aspects</topic><topic>Humans</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Inhibitory Concentration 50</topic><topic>Isobenzofuranones</topic><topic>Medical sciences</topic><topic>Oxygen - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Phthalides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Logrado, Lúcio P.L.</creatorcontrib><creatorcontrib>Santos, Camila O.</creatorcontrib><creatorcontrib>Romeiro, Luiz A.S.</creatorcontrib><creatorcontrib>Costa, Arinice M.</creatorcontrib><creatorcontrib>Ferreira, José R.O.</creatorcontrib><creatorcontrib>Cavalcanti, Bruno C.</creatorcontrib><creatorcontrib>Manoel de Moraes, O.</creatorcontrib><creatorcontrib>Costa-Lotufo, Letícia V.</creatorcontrib><creatorcontrib>Pessoa, Cláudia</creatorcontrib><creatorcontrib>dos Santos, Maria L.</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>Logrado, Lúcio P.L.</au><au>Santos, Camila O.</au><au>Romeiro, Luiz A.S.</au><au>Costa, Arinice M.</au><au>Ferreira, José R.O.</au><au>Cavalcanti, Bruno C.</au><au>Manoel de Moraes, O.</au><au>Costa-Lotufo, Letícia V.</au><au>Pessoa, Cláudia</au><au>dos Santos, Maria L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2010-08-01</date><risdate>2010</risdate><volume>45</volume><issue>8</issue><spage>3480</spage><epage>3489</epage><pages>3480-3489</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>This work is part of a large program, which seeks to discover new antitumor isobenfuranones designed from anacardic acids. The synthetic strategy for the construction of the title compounds takes into consideration the use of inexpensive anacardic acids (
2), the major natural cashew (
Anacardium occidentale) nut-shell phenolic lipid, and features one-pot construction of fused-ring aromatic γ-lactones, phthalides. The cytotoxicity screening in different human cancer cell lines (HL-60 leukemia, SF295 glioblastoma and MDA-MB435 melanoma) by the MTT assay showed that acyclic precursor (
6), and isobenfuranones (
1a and
1b) are active compounds. Interestingly,
1a exhibits significant antiproliferative effect against HL-60 cells and moderate activity against SF295 and MDA-MB435 cell lines. Analysis of mechanisms involved in the cytotoxic activity showed that active compounds were leading to DNA damage, triggering apoptosis or necrosis induction.
A simple approach to isobenzofuranones from anacardic acids is described. Compound (
1b) showed a discriminatory antiproliferative effects against HL-60 cells.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>20537433</pmid><doi>10.1016/j.ejmech.2010.05.015</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2010-08, Vol.45 (8), p.3480-3489 |
| issn | 0223-5234 1768-3254 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Anacardic acids Anacardic Acids - chemistry Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Apoptosis - drug effects Benzofurans - chemical synthesis Benzofurans - chemistry Benzofurans - pharmacology Biological and medical sciences Cell Line, Tumor Cell Proliferation - drug effects Cell Survival - drug effects Cytotoxicity screening Drug Design Drug Evaluation, Preclinical - methods General aspects Humans Hydrophobic and Hydrophilic Interactions Inhibitory Concentration 50 Isobenzofuranones Medical sciences Oxygen - chemistry Pharmacology. Drug treatments Phthalides |
| title | Synthesis and cytotoxicity screening of substituted isobenzofuranones designed from anacardic acids |
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