Pleuromutilin derivatives having a purine ring. Part 2: Influence of the central spacer on the antibacterial activity against Gram-positive pathogens
Structural modification of the 4-piperidinethio moiety, as a central spacer of the pleuromutilin analogues 2A and 2B with excellent in vitro and in vivo antibacterial activities and good solubility in water, led to the discovery of the novel and promising compounds 14B and 17B. Structural modificati...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2009, Vol.19 (1), p.170-174 |
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| container_end_page | 174 |
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| container_start_page | 170 |
| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Hirokawa, Yoshimi Kinoshita, Hironori Tanaka, Tomoyuki Nakamura, Takanori Fujimoto, Koichi Kashimoto, Shigeki Kojima, Tsuyoshi Kato, Shiro |
| description | Structural modification of the 4-piperidinethio moiety, as a central spacer of the pleuromutilin analogues
2A and
2B with excellent in vitro and in vivo antibacterial activities and good solubility in water, led to the discovery of the novel and promising compounds
14B and
17B.
Structural modification of the 4-piperidinethio moiety, as a spacer of the first pleuromutilin analogues
2A and
2B having a purine ring, led to discovery of the novel pleuromutilin derivatives
14B and
17B. These compounds with good solubility in water showed promising in vitro antibacterial activity against various Gram-positive bacteria including MRSA, PRSP, and VRE and have potent in vivo efficacy. |
| doi_str_mv | 10.1016/j.bmcl.2008.10.123 |
| format | Article |
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2A and
2B with excellent in vitro and in vivo antibacterial activities and good solubility in water, led to the discovery of the novel and promising compounds
14B and
17B.
Structural modification of the 4-piperidinethio moiety, as a spacer of the first pleuromutilin analogues
2A and
2B having a purine ring, led to discovery of the novel pleuromutilin derivatives
14B and
17B. These compounds with good solubility in water showed promising in vitro antibacterial activity against various Gram-positive bacteria including MRSA, PRSP, and VRE and have potent in vivo efficacy.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2008.10.123</identifier><identifier>PMID: 19028096</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Biological and medical sciences ; Diterpenes - chemistry ; Gram-positive bacteria ; Gram-Positive Bacteria - drug effects ; Medical sciences ; MIC ; Microbial Sensitivity Tests ; MRSA ; Pharmacology. Drug treatments ; Piperazine ring ; Pleuromutilin ; Pleuromutilins ; Polycyclic Compounds ; PRSP ; Purine ring ; Purines - chemistry ; Solubility ; Spacer ; Structure-Activity Relationship ; Sulfide ; VRE</subject><ispartof>Bioorganic & medicinal chemistry letters, 2009, Vol.19 (1), p.170-174</ispartof><rights>2008 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c512t-3b1087cbfbe136104bb500f8d0b2725c03c282cfd86752466ae968ae4daa9e253</citedby><cites>FETCH-LOGICAL-c512t-3b1087cbfbe136104bb500f8d0b2725c03c282cfd86752466ae968ae4daa9e253</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X08013395$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,4009,27902,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21030115$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19028096$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hirokawa, Yoshimi</creatorcontrib><creatorcontrib>Kinoshita, Hironori</creatorcontrib><creatorcontrib>Tanaka, Tomoyuki</creatorcontrib><creatorcontrib>Nakamura, Takanori</creatorcontrib><creatorcontrib>Fujimoto, Koichi</creatorcontrib><creatorcontrib>Kashimoto, Shigeki</creatorcontrib><creatorcontrib>Kojima, Tsuyoshi</creatorcontrib><creatorcontrib>Kato, Shiro</creatorcontrib><title>Pleuromutilin derivatives having a purine ring. Part 2: Influence of the central spacer on the antibacterial activity against Gram-positive pathogens</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Structural modification of the 4-piperidinethio moiety, as a central spacer of the pleuromutilin analogues
2A and
2B with excellent in vitro and in vivo antibacterial activities and good solubility in water, led to the discovery of the novel and promising compounds
14B and
17B.
Structural modification of the 4-piperidinethio moiety, as a spacer of the first pleuromutilin analogues
2A and
2B having a purine ring, led to discovery of the novel pleuromutilin derivatives
14B and
17B. These compounds with good solubility in water showed promising in vitro antibacterial activity against various Gram-positive bacteria including MRSA, PRSP, and VRE and have potent in vivo efficacy.</description><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Diterpenes - chemistry</subject><subject>Gram-positive bacteria</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Medical sciences</subject><subject>MIC</subject><subject>Microbial Sensitivity Tests</subject><subject>MRSA</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperazine ring</subject><subject>Pleuromutilin</subject><subject>Pleuromutilins</subject><subject>Polycyclic Compounds</subject><subject>PRSP</subject><subject>Purine ring</subject><subject>Purines - chemistry</subject><subject>Solubility</subject><subject>Spacer</subject><subject>Structure-Activity Relationship</subject><subject>Sulfide</subject><subject>VRE</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkcFu1DAQhiMEokvhBTggX-CWMHYcx0FcUAWlUiV6AIlbNHEmu14lTrCdSH0Q3peku4IbcLGtf775Z-Q_SV5yyDhw9faYNYPpMwGgs00T-aNkx6WSaS6heJzsoFKQ6kp-v0iehXAE4BKkfJpc8AqEXqu75OddT7Mfhzna3jrWkrcLRrtQYAdcrNszZNPsrSO2HvuM3aGPTLxjN67rZ3KG2NixeCBmyEWPPQsTGvJsdA8qumgbNHH1XWvrwy423jPco3UhsmuPQzqNwW4j2YTxMO7JhefJkw77QC_O92Xy7dPHr1ef09sv1zdXH25TU3AR07zhoEvTdA3xXHGQTVMAdLqFRpSiMJAboYXpWq3KQkilkCqlkWSLWJEo8svkzcl38uOPmUKsBxsM9T06GudQK1Wqqiz0P0EBueRaqv8AhRJFuY0WJ9D4MQRPXT15O6C_rznUW7z1sd7irbd4HzSRr02vzu5zM1D7p-Wc5wq8PgMYDPadR2ds-M0JDjlwvk1_f-Jo_d3Fkq-DsVuarfVkYt2O9m97_AJlrcVd</recordid><startdate>2009</startdate><enddate>2009</enddate><creator>Hirokawa, Yoshimi</creator><creator>Kinoshita, Hironori</creator><creator>Tanaka, Tomoyuki</creator><creator>Nakamura, Takanori</creator><creator>Fujimoto, Koichi</creator><creator>Kashimoto, Shigeki</creator><creator>Kojima, Tsuyoshi</creator><creator>Kato, Shiro</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>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>2009</creationdate><title>Pleuromutilin derivatives having a purine ring. Part 2: Influence of the central spacer on the antibacterial activity against Gram-positive pathogens</title><author>Hirokawa, Yoshimi ; Kinoshita, Hironori ; Tanaka, Tomoyuki ; Nakamura, Takanori ; Fujimoto, Koichi ; Kashimoto, Shigeki ; Kojima, Tsuyoshi ; Kato, Shiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c512t-3b1087cbfbe136104bb500f8d0b2725c03c282cfd86752466ae968ae4daa9e253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Diterpenes - chemistry</topic><topic>Gram-positive bacteria</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>Medical sciences</topic><topic>MIC</topic><topic>Microbial Sensitivity Tests</topic><topic>MRSA</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperazine ring</topic><topic>Pleuromutilin</topic><topic>Pleuromutilins</topic><topic>Polycyclic Compounds</topic><topic>PRSP</topic><topic>Purine ring</topic><topic>Purines - chemistry</topic><topic>Solubility</topic><topic>Spacer</topic><topic>Structure-Activity Relationship</topic><topic>Sulfide</topic><topic>VRE</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hirokawa, Yoshimi</creatorcontrib><creatorcontrib>Kinoshita, Hironori</creatorcontrib><creatorcontrib>Tanaka, Tomoyuki</creatorcontrib><creatorcontrib>Nakamura, Takanori</creatorcontrib><creatorcontrib>Fujimoto, Koichi</creatorcontrib><creatorcontrib>Kashimoto, Shigeki</creatorcontrib><creatorcontrib>Kojima, Tsuyoshi</creatorcontrib><creatorcontrib>Kato, Shiro</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>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hirokawa, Yoshimi</au><au>Kinoshita, Hironori</au><au>Tanaka, Tomoyuki</au><au>Nakamura, Takanori</au><au>Fujimoto, Koichi</au><au>Kashimoto, Shigeki</au><au>Kojima, Tsuyoshi</au><au>Kato, Shiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pleuromutilin derivatives having a purine ring. Part 2: Influence of the central spacer on the antibacterial activity against Gram-positive pathogens</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2009</date><risdate>2009</risdate><volume>19</volume><issue>1</issue><spage>170</spage><epage>174</epage><pages>170-174</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Structural modification of the 4-piperidinethio moiety, as a central spacer of the pleuromutilin analogues
2A and
2B with excellent in vitro and in vivo antibacterial activities and good solubility in water, led to the discovery of the novel and promising compounds
14B and
17B.
Structural modification of the 4-piperidinethio moiety, as a spacer of the first pleuromutilin analogues
2A and
2B having a purine ring, led to discovery of the novel pleuromutilin derivatives
14B and
17B. These compounds with good solubility in water showed promising in vitro antibacterial activity against various Gram-positive bacteria including MRSA, PRSP, and VRE and have potent in vivo efficacy.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19028096</pmid><doi>10.1016/j.bmcl.2008.10.123</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Bioorganic & medicinal chemistry letters, 2009, Vol.19 (1), p.170-174 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Diterpenes - chemistry Gram-positive bacteria Gram-Positive Bacteria - drug effects Medical sciences MIC Microbial Sensitivity Tests MRSA Pharmacology. Drug treatments Piperazine ring Pleuromutilin Pleuromutilins Polycyclic Compounds PRSP Purine ring Purines - chemistry Solubility Spacer Structure-Activity Relationship Sulfide VRE |
| title | Pleuromutilin derivatives having a purine ring. Part 2: Influence of the central spacer on the antibacterial activity against Gram-positive pathogens |
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