Antitumor Activity of 9(R)-Dihydrotaxane Analogs
A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solu...
Gespeichert in:
| Veröffentlicht in: | Journal of medicinal chemistry 1995-04, Vol.38 (9), p.1482-1492 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1492 |
|---|---|
| container_issue | 9 |
| container_start_page | 1482 |
| container_title | Journal of medicinal chemistry |
| container_volume | 38 |
| creator | Klein, Larry L Li, Leping Maring, Clarence J Yeung, Clinton M Thomas, Sheela A Grampovnik, David J Plattner, Jacob J |
| description | A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity. |
| doi_str_mv | 10.1021/jm00009a009 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_77264109</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>77264109</sourcerecordid><originalsourceid>FETCH-LOGICAL-a383t-d3db4b72e9c8e420695496699699edf415731f78f55fe54fb16625df1f7392aa3</originalsourceid><addsrcrecordid>eNpt0FtLwzAUB_AgypzTJ5-FPYgXpJpLkzSPZd6dKDp98CVkbaKdvcykle3bG2kZPhgSDuT8OBz-AOwieIogRmezAvojlH9roI8ohkEYwXAd9CHEOMAMk02w5dzMK4Iw6YEe50RAyPsAxmWd1U1R2WGc1Nl3Vi-HlRmKo6fj4Dz7WKa2qtVClXoYlyqv3t022DAqd3qnqwPwcnkxGV0H44erm1E8DhSJSB2kJJ2GU461SCIdYsgEDQVjQvirUxMiygkyPDKUGk1DM0WMYZoa_0cEVooMwEE7d26rr0a7WhaZS3Se-12qxknOMQsRFB6etDCxlXNWGzm3WaHsUiIof_ORf_Lxeq8b20wLna5sF4jv73d95RKVG6vKJHMrRihmUUQ9C1qWuVovVm1lPyXjhFM5eXyW_P7t9o5HrxJ6f9h6lTg5qxrrw3T_LvgDqROFwA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>77264109</pqid></control><display><type>article</type><title>Antitumor Activity of 9(R)-Dihydrotaxane Analogs</title><source>MEDLINE</source><source>ACS Publications</source><creator>Klein, Larry L ; Li, Leping ; Maring, Clarence J ; Yeung, Clinton M ; Thomas, Sheela A ; Grampovnik, David J ; Plattner, Jacob J</creator><creatorcontrib>Klein, Larry L ; Li, Leping ; Maring, Clarence J ; Yeung, Clinton M ; Thomas, Sheela A ; Grampovnik, David J ; Plattner, Jacob J</creatorcontrib><description>A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00009a009</identifier><identifier>PMID: 7739007</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - pharmacology ; Biological and medical sciences ; General aspects ; Humans ; Medical sciences ; Mice ; Paclitaxel - analogs & derivatives ; Paclitaxel - chemistry ; Paclitaxel - pharmacology ; Pharmacology. Drug treatments ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 1995-04, Vol.38 (9), p.1482-1492</ispartof><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a383t-d3db4b72e9c8e420695496699699edf415731f78f55fe54fb16625df1f7392aa3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00009a009$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00009a009$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3526885$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7739007$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Klein, Larry L</creatorcontrib><creatorcontrib>Li, Leping</creatorcontrib><creatorcontrib>Maring, Clarence J</creatorcontrib><creatorcontrib>Yeung, Clinton M</creatorcontrib><creatorcontrib>Thomas, Sheela A</creatorcontrib><creatorcontrib>Grampovnik, David J</creatorcontrib><creatorcontrib>Plattner, Jacob J</creatorcontrib><title>Antitumor Activity of 9(R)-Dihydrotaxane Analogs</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biological and medical sciences</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Paclitaxel - analogs & derivatives</subject><subject>Paclitaxel - chemistry</subject><subject>Paclitaxel - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Tumor Cells, Cultured</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0FtLwzAUB_AgypzTJ5-FPYgXpJpLkzSPZd6dKDp98CVkbaKdvcykle3bG2kZPhgSDuT8OBz-AOwieIogRmezAvojlH9roI8ohkEYwXAd9CHEOMAMk02w5dzMK4Iw6YEe50RAyPsAxmWd1U1R2WGc1Nl3Vi-HlRmKo6fj4Dz7WKa2qtVClXoYlyqv3t022DAqd3qnqwPwcnkxGV0H44erm1E8DhSJSB2kJJ2GU461SCIdYsgEDQVjQvirUxMiygkyPDKUGk1DM0WMYZoa_0cEVooMwEE7d26rr0a7WhaZS3Se-12qxknOMQsRFB6etDCxlXNWGzm3WaHsUiIof_ORf_Lxeq8b20wLna5sF4jv73d95RKVG6vKJHMrRihmUUQ9C1qWuVovVm1lPyXjhFM5eXyW_P7t9o5HrxJ6f9h6lTg5qxrrw3T_LvgDqROFwA</recordid><startdate>19950401</startdate><enddate>19950401</enddate><creator>Klein, Larry L</creator><creator>Li, Leping</creator><creator>Maring, Clarence J</creator><creator>Yeung, Clinton M</creator><creator>Thomas, Sheela A</creator><creator>Grampovnik, David J</creator><creator>Plattner, Jacob J</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>19950401</creationdate><title>Antitumor Activity of 9(R)-Dihydrotaxane Analogs</title><author>Klein, Larry L ; Li, Leping ; Maring, Clarence J ; Yeung, Clinton M ; Thomas, Sheela A ; Grampovnik, David J ; Plattner, Jacob J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a383t-d3db4b72e9c8e420695496699699edf415731f78f55fe54fb16625df1f7392aa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biological and medical sciences</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Paclitaxel - analogs & derivatives</topic><topic>Paclitaxel - chemistry</topic><topic>Paclitaxel - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Klein, Larry L</creatorcontrib><creatorcontrib>Li, Leping</creatorcontrib><creatorcontrib>Maring, Clarence J</creatorcontrib><creatorcontrib>Yeung, Clinton M</creatorcontrib><creatorcontrib>Thomas, Sheela A</creatorcontrib><creatorcontrib>Grampovnik, David J</creatorcontrib><creatorcontrib>Plattner, Jacob J</creatorcontrib><collection>Istex</collection><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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Klein, Larry L</au><au>Li, Leping</au><au>Maring, Clarence J</au><au>Yeung, Clinton M</au><au>Thomas, Sheela A</au><au>Grampovnik, David J</au><au>Plattner, Jacob J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antitumor Activity of 9(R)-Dihydrotaxane Analogs</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1995-04-01</date><risdate>1995</risdate><volume>38</volume><issue>9</issue><spage>1482</spage><epage>1492</epage><pages>1482-1492</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A novel reduced taxane, 13-acetyl-9(R)-dihydrobaccatin III (1) has been isolated from Taxus canadensis. The selective C-13 deacetylation of this isolate has allowed for the preparation of a wide variety of 9(R)-dihydrotaxane analogs. In general, this series has shown greater stability and water solubility than the 9-carbonyl series while retaining antimicrotubule and tumor cell cytotoxicity activities relative to taxol. Placement of polar functionalities at the C-7 position results in loss of activity whereas alkylation or acylation of either C-7 or C-9 hydroxyl groups ameliorate the activity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>7739007</pmid><doi>10.1021/jm00009a009</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1995-04, Vol.38 (9), p.1482-1492 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_77264109 |
| source | MEDLINE; ACS Publications |
| subjects | Animals Antineoplastic agents Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences General aspects Humans Medical sciences Mice Paclitaxel - analogs & derivatives Paclitaxel - chemistry Paclitaxel - pharmacology Pharmacology. Drug treatments Tumor Cells, Cultured |
| title | Antitumor Activity of 9(R)-Dihydrotaxane Analogs |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-15T22%3A54%3A39IST&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=Antitumor%20Activity%20of%209(R)-Dihydrotaxane%20Analogs&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Klein,%20Larry%20L&rft.date=1995-04-01&rft.volume=38&rft.issue=9&rft.spage=1482&rft.epage=1492&rft.pages=1482-1492&rft.issn=0022-2623&rft.eissn=1520-4804&rft.coden=JMCMAR&rft_id=info:doi/10.1021/jm00009a009&rft_dat=%3Cproquest_cross%3E77264109%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=77264109&rft_id=info:pmid/7739007&rfr_iscdi=true |