Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars
4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide ( 3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide ( 2c) by a bromo-radical substitution reaction occurred at C-4 position by NBS and AIBN. The novel phospha sugar analogue exerted high anti-proliferative effect on U937 ce...
Gespeichert in:
| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-10, Vol.20 (19), p.5943-5946 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5946 |
|---|---|
| container_issue | 19 |
| container_start_page | 5943 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 20 |
| creator | Yamada, Manabu Yamashita, Mitsuji Suyama, Takuya Yamashita, Junko Asai, Kazuhide Niimi, Taishi Ozaki, Nobuhisa Fujie, Michio Maddali, Kasthuraiah Nakamura, Satoki Ohnishi, Kazunori |
| description | 4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
2c) by a bromo-radical substitution reaction occurred at C-4 position by NBS and AIBN. The novel phospha sugar analogue exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec®, which is known as a molecule targeting chemotherapeutical agent.
4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
2c) by a bromo-radical substitution reaction occurred at C-4 position by
N-bromosuccinimide and 2,2′-azobisisobutyronitrile. The novel phospha sugar analogue
3c exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec®, which is known as a molecule targeting chemotherapeutical agent. The substitution of 2-phospholenes at C-3 and C-4 position with methyl groups as well as 4-bromo substituent suggests a good anti-proliferative effect. |
| doi_str_mv | 10.1016/j.bmcl.2010.01.061 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_754004597</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0960894X10000739</els_id><sourcerecordid>754004597</sourcerecordid><originalsourceid>FETCH-LOGICAL-c385t-492586dc564068ceb83ead0723118b82c3e4241e4da4552b8997039e7e5b13ef3</originalsourceid><addsrcrecordid>eNp9kcuO1DAQRS0EYpqBH2CBskFscFN-JY7EBo14SSPBAiR2luNUJm45cWOnRzR_wt_ing6wY2HVw6euS76EPGWwZcDqV7ttN7mw5VAawLZQs3tkw2QtqZCg7pMNtDVQ3cpvF-RRzjsAJkHKh-SCgy5Dgm3Ir88J9zbZxce5snNfubFUbsHkf56bcajmeIuhkrRLcYpUvJS09xMu4zFQRvcjziXhJYm5nIAzVozGH77HO8VlPEUb4k085GqlUklHLM9Ed3QBcxXTemWrfLixKT8mDwYbMj5Z4yX5-u7tl6sP9PrT-49Xb66pE1otVLZc6bp3qpZQa4edFmh7aLhgTHeaO4GSS4ayt1Ip3um2bUC02KDqmMBBXJIXZ919it8PmBcz-ewwBDtjWdg0SgJI1TaF5GfSpZhzwsHsk59sOhoG5uSI2ZmTI-bkiAFmiiNl6Nkqf-gm7P-O_LGgAM9XwGZnw5Ds7Hz-xwneAL8Ten3msHzGrcdksvM4O-x9QreYPvr_7fEbuH-rPQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>754004597</pqid></control><display><type>article</type><title>Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars</title><source>MEDLINE</source><source>Access via ScienceDirect (Elsevier)</source><creator>Yamada, Manabu ; Yamashita, Mitsuji ; Suyama, Takuya ; Yamashita, Junko ; Asai, Kazuhide ; Niimi, Taishi ; Ozaki, Nobuhisa ; Fujie, Michio ; Maddali, Kasthuraiah ; Nakamura, Satoki ; Ohnishi, Kazunori</creator><creatorcontrib>Yamada, Manabu ; Yamashita, Mitsuji ; Suyama, Takuya ; Yamashita, Junko ; Asai, Kazuhide ; Niimi, Taishi ; Ozaki, Nobuhisa ; Fujie, Michio ; Maddali, Kasthuraiah ; Nakamura, Satoki ; Ohnishi, Kazunori</creatorcontrib><description>4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
2c) by a bromo-radical substitution reaction occurred at C-4 position by NBS and AIBN. The novel phospha sugar analogue exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec®, which is known as a molecule targeting chemotherapeutical agent.
4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
2c) by a bromo-radical substitution reaction occurred at C-4 position by
N-bromosuccinimide and 2,2′-azobisisobutyronitrile. The novel phospha sugar analogue
3c exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec®, which is known as a molecule targeting chemotherapeutical agent. The substitution of 2-phospholenes at C-3 and C-4 position with methyl groups as well as 4-bromo substituent suggests a good anti-proliferative effect.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.01.061</identifier><identifier>PMID: 20801031</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - toxicity ; Benzamides ; Biological and medical sciences ; Cell Line, Tumor ; Cyclic P-Oxides - chemical synthesis ; Cyclic P-Oxides - chemistry ; Cyclic P-Oxides - toxicity ; General aspects ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - toxicity ; Humans ; Imatinib Mesylate ; Leukemia cells ; Medical sciences ; MTT in vitro method ; Organophosphorus Compounds - chemical synthesis ; Organophosphorus Compounds - chemistry ; Organophosphorus Compounds - toxicity ; Pharmacology. Drug treatments ; Phospha sugars ; Phosphorus - chemistry ; Phosphorus heterocycles ; Piperazines - toxicity ; Pyrimidines - toxicity ; Tumors</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-10, Vol.20 (19), p.5943-5946</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c385t-492586dc564068ceb83ead0723118b82c3e4241e4da4552b8997039e7e5b13ef3</citedby><cites>FETCH-LOGICAL-c385t-492586dc564068ceb83ead0723118b82c3e4241e4da4552b8997039e7e5b13ef3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2010.01.061$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23270261$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20801031$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yamada, Manabu</creatorcontrib><creatorcontrib>Yamashita, Mitsuji</creatorcontrib><creatorcontrib>Suyama, Takuya</creatorcontrib><creatorcontrib>Yamashita, Junko</creatorcontrib><creatorcontrib>Asai, Kazuhide</creatorcontrib><creatorcontrib>Niimi, Taishi</creatorcontrib><creatorcontrib>Ozaki, Nobuhisa</creatorcontrib><creatorcontrib>Fujie, Michio</creatorcontrib><creatorcontrib>Maddali, Kasthuraiah</creatorcontrib><creatorcontrib>Nakamura, Satoki</creatorcontrib><creatorcontrib>Ohnishi, Kazunori</creatorcontrib><title>Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
2c) by a bromo-radical substitution reaction occurred at C-4 position by NBS and AIBN. The novel phospha sugar analogue exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec®, which is known as a molecule targeting chemotherapeutical agent.
4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
2c) by a bromo-radical substitution reaction occurred at C-4 position by
N-bromosuccinimide and 2,2′-azobisisobutyronitrile. The novel phospha sugar analogue
3c exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec®, which is known as a molecule targeting chemotherapeutical agent. The substitution of 2-phospholenes at C-3 and C-4 position with methyl groups as well as 4-bromo substituent suggests a good anti-proliferative effect.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - toxicity</subject><subject>Benzamides</subject><subject>Biological and medical sciences</subject><subject>Cell Line, Tumor</subject><subject>Cyclic P-Oxides - chemical synthesis</subject><subject>Cyclic P-Oxides - chemistry</subject><subject>Cyclic P-Oxides - toxicity</subject><subject>General aspects</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - toxicity</subject><subject>Humans</subject><subject>Imatinib Mesylate</subject><subject>Leukemia cells</subject><subject>Medical sciences</subject><subject>MTT in vitro method</subject><subject>Organophosphorus Compounds - chemical synthesis</subject><subject>Organophosphorus Compounds - chemistry</subject><subject>Organophosphorus Compounds - toxicity</subject><subject>Pharmacology. Drug treatments</subject><subject>Phospha sugars</subject><subject>Phosphorus - chemistry</subject><subject>Phosphorus heterocycles</subject><subject>Piperazines - toxicity</subject><subject>Pyrimidines - toxicity</subject><subject>Tumors</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kcuO1DAQRS0EYpqBH2CBskFscFN-JY7EBo14SSPBAiR2luNUJm45cWOnRzR_wt_ing6wY2HVw6euS76EPGWwZcDqV7ttN7mw5VAawLZQs3tkw2QtqZCg7pMNtDVQ3cpvF-RRzjsAJkHKh-SCgy5Dgm3Ir88J9zbZxce5snNfubFUbsHkf56bcajmeIuhkrRLcYpUvJS09xMu4zFQRvcjziXhJYm5nIAzVozGH77HO8VlPEUb4k085GqlUklHLM9Ed3QBcxXTemWrfLixKT8mDwYbMj5Z4yX5-u7tl6sP9PrT-49Xb66pE1otVLZc6bp3qpZQa4edFmh7aLhgTHeaO4GSS4ayt1Ip3um2bUC02KDqmMBBXJIXZ919it8PmBcz-ewwBDtjWdg0SgJI1TaF5GfSpZhzwsHsk59sOhoG5uSI2ZmTI-bkiAFmiiNl6Nkqf-gm7P-O_LGgAM9XwGZnw5Ds7Hz-xwneAL8Ten3msHzGrcdksvM4O-x9QreYPvr_7fEbuH-rPQ</recordid><startdate>20101001</startdate><enddate>20101001</enddate><creator>Yamada, Manabu</creator><creator>Yamashita, Mitsuji</creator><creator>Suyama, Takuya</creator><creator>Yamashita, Junko</creator><creator>Asai, Kazuhide</creator><creator>Niimi, Taishi</creator><creator>Ozaki, Nobuhisa</creator><creator>Fujie, Michio</creator><creator>Maddali, Kasthuraiah</creator><creator>Nakamura, Satoki</creator><creator>Ohnishi, Kazunori</creator><general>Elsevier Ltd</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>20101001</creationdate><title>Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars</title><author>Yamada, Manabu ; Yamashita, Mitsuji ; Suyama, Takuya ; Yamashita, Junko ; Asai, Kazuhide ; Niimi, Taishi ; Ozaki, Nobuhisa ; Fujie, Michio ; Maddali, Kasthuraiah ; Nakamura, Satoki ; Ohnishi, Kazunori</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-492586dc564068ceb83ead0723118b82c3e4241e4da4552b8997039e7e5b13ef3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - toxicity</topic><topic>Benzamides</topic><topic>Biological and medical sciences</topic><topic>Cell Line, Tumor</topic><topic>Cyclic P-Oxides - chemical synthesis</topic><topic>Cyclic P-Oxides - chemistry</topic><topic>Cyclic P-Oxides - toxicity</topic><topic>General aspects</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic Compounds - toxicity</topic><topic>Humans</topic><topic>Imatinib Mesylate</topic><topic>Leukemia cells</topic><topic>Medical sciences</topic><topic>MTT in vitro method</topic><topic>Organophosphorus Compounds - chemical synthesis</topic><topic>Organophosphorus Compounds - chemistry</topic><topic>Organophosphorus Compounds - toxicity</topic><topic>Pharmacology. Drug treatments</topic><topic>Phospha sugars</topic><topic>Phosphorus - chemistry</topic><topic>Phosphorus heterocycles</topic><topic>Piperazines - toxicity</topic><topic>Pyrimidines - toxicity</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamada, Manabu</creatorcontrib><creatorcontrib>Yamashita, Mitsuji</creatorcontrib><creatorcontrib>Suyama, Takuya</creatorcontrib><creatorcontrib>Yamashita, Junko</creatorcontrib><creatorcontrib>Asai, Kazuhide</creatorcontrib><creatorcontrib>Niimi, Taishi</creatorcontrib><creatorcontrib>Ozaki, Nobuhisa</creatorcontrib><creatorcontrib>Fujie, Michio</creatorcontrib><creatorcontrib>Maddali, Kasthuraiah</creatorcontrib><creatorcontrib>Nakamura, Satoki</creatorcontrib><creatorcontrib>Ohnishi, Kazunori</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamada, Manabu</au><au>Yamashita, Mitsuji</au><au>Suyama, Takuya</au><au>Yamashita, Junko</au><au>Asai, Kazuhide</au><au>Niimi, Taishi</au><au>Ozaki, Nobuhisa</au><au>Fujie, Michio</au><au>Maddali, Kasthuraiah</au><au>Nakamura, Satoki</au><au>Ohnishi, Kazunori</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010-10-01</date><risdate>2010</risdate><volume>20</volume><issue>19</issue><spage>5943</spage><epage>5946</epage><pages>5943-5946</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
2c) by a bromo-radical substitution reaction occurred at C-4 position by NBS and AIBN. The novel phospha sugar analogue exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec®, which is known as a molecule targeting chemotherapeutical agent.
4-Bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
3c) was first synthesized from 3,4-dimethyl-1-phenyl-2-phospholene 1-oxide (
2c) by a bromo-radical substitution reaction occurred at C-4 position by
N-bromosuccinimide and 2,2′-azobisisobutyronitrile. The novel phospha sugar analogue
3c exerted high anti-proliferative effect on U937 cells evaluated by MTT in vitro methods and was much more efficient than that of Gleevec®, which is known as a molecule targeting chemotherapeutical agent. The substitution of 2-phospholenes at C-3 and C-4 position with methyl groups as well as 4-bromo substituent suggests a good anti-proliferative effect.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20801031</pmid><doi>10.1016/j.bmcl.2010.01.061</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2010-10, Vol.20 (19), p.5943-5946 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_754004597 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - toxicity Benzamides Biological and medical sciences Cell Line, Tumor Cyclic P-Oxides - chemical synthesis Cyclic P-Oxides - chemistry Cyclic P-Oxides - toxicity General aspects Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Heterocyclic Compounds - toxicity Humans Imatinib Mesylate Leukemia cells Medical sciences MTT in vitro method Organophosphorus Compounds - chemical synthesis Organophosphorus Compounds - chemistry Organophosphorus Compounds - toxicity Pharmacology. Drug treatments Phospha sugars Phosphorus - chemistry Phosphorus heterocycles Piperazines - toxicity Pyrimidines - toxicity Tumors |
| title | Preparation and characterization of novel 4-bromo-3,4-dimethyl-1-phenyl-2-phospholene 1-oxide and the analogous phosphorus heterocycles or phospha sugars |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T06%3A03%3A30IST&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=Preparation%20and%20characterization%20of%20novel%204-bromo-3,4-dimethyl-1-phenyl-2-phospholene%201-oxide%20and%20the%20analogous%20phosphorus%20heterocycles%20or%20phospha%20sugars&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry%20letters&rft.au=Yamada,%20Manabu&rft.date=2010-10-01&rft.volume=20&rft.issue=19&rft.spage=5943&rft.epage=5946&rft.pages=5943-5946&rft.issn=0960-894X&rft.eissn=1464-3405&rft_id=info:doi/10.1016/j.bmcl.2010.01.061&rft_dat=%3Cproquest_cross%3E754004597%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=754004597&rft_id=info:pmid/20801031&rft_els_id=S0960894X10000739&rfr_iscdi=true |