Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents
A new series of carbamate prodrugs of SQ109 is disclosed. Bioavailability of SQ109 after administration of prodrug 7a was 91.4% compared with 21.4% after oral administration of SQ109. After oral administration of compound 7a, the parent drug SQ109 exhibited preferential tissue distribution into lung...
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Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2009-05, Vol.19 (10), p.2808-2810 |
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creator | Meng, Qingyi Luo, Huibing Liu, Yibin Li, Wei Zhang, Wen Yao, Qizheng |
description | A new series of carbamate prodrugs of
SQ109 is disclosed. Bioavailability of
SQ109 after administration of prodrug
7a was 91.4% compared with 21.4% after oral administration of
SQ109. After oral administration of compound
7a, the parent drug
SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication.
The low bioavailability of
SQ109 in rats, resulting from first-pass effect in the liver, may be remedied by prodrug strategy. Based on esterase-sensitive carbamate prodrug strategy, a novel series of prodrugs of
SQ109 has been reported. Bioavailability of
SQ109 after administration of prodrug
7a was 91.4% compared with 21.4% after oral administration of
SQ109. After oral administration of compound
7a, the parent drug
SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication. |
doi_str_mv | 10.1016/j.bmcl.2009.03.091 |
format | Article |
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SQ109 is disclosed. Bioavailability of
SQ109 after administration of prodrug
7a was 91.4% compared with 21.4% after oral administration of
SQ109. After oral administration of compound
7a, the parent drug
SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication.
The low bioavailability of
SQ109 in rats, resulting from first-pass effect in the liver, may be remedied by prodrug strategy. Based on esterase-sensitive carbamate prodrug strategy, a novel series of prodrugs of
SQ109 has been reported. Bioavailability of
SQ109 after administration of prodrug
7a was 91.4% compared with 21.4% after oral administration of
SQ109. After oral administration of compound
7a, the parent drug
SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2009.03.091</identifier><identifier>PMID: 19362471</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject><![CDATA[Adamantane - administration & dosage ; Adamantane - analogs & derivatives ; Adamantane - chemical synthesis ; Adamantane - chemistry ; Administration, Oral ; Animals ; Anti-tuberculosis ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antitubercular Agents - administration & dosage ; Antitubercular Agents - chemical synthesis ; Antitubercular Agents - chemistry ; Bioavailability ; Biological and medical sciences ; Carbamates - administration & dosage ; Carbamates - chemical synthesis ; Carbamates - chemistry ; Ethylenediamines - administration & dosage ; Ethylenediamines - chemical synthesis ; Ethylenediamines - chemistry ; General pharmacology ; Medical sciences ; Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions ; Pharmacology. Drug treatments ; Prodrug ; Prodrugs - administration & dosage ; Prodrugs - chemical synthesis ; Prodrugs - chemistry ; Rats ; SQ109 ; Tissue Distribution]]></subject><ispartof>Bioorganic & medicinal chemistry letters, 2009-05, Vol.19 (10), p.2808-2810</ispartof><rights>2009 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c481t-f1263ec13f03af3d3fca70fc6671d977f710d094602960817336575b456eb7663</citedby><cites>FETCH-LOGICAL-c481t-f1263ec13f03af3d3fca70fc6671d977f710d094602960817336575b456eb7663</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.2009.03.091$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21496195$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19362471$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Meng, Qingyi</creatorcontrib><creatorcontrib>Luo, Huibing</creatorcontrib><creatorcontrib>Liu, Yibin</creatorcontrib><creatorcontrib>Li, Wei</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><creatorcontrib>Yao, Qizheng</creatorcontrib><title>Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A new series of carbamate prodrugs of
SQ109 is disclosed. Bioavailability of
SQ109 after administration of prodrug
7a was 91.4% compared with 21.4% after oral administration of
SQ109. After oral administration of compound
7a, the parent drug
SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication.
The low bioavailability of
SQ109 in rats, resulting from first-pass effect in the liver, may be remedied by prodrug strategy. Based on esterase-sensitive carbamate prodrug strategy, a novel series of prodrugs of
SQ109 has been reported. Bioavailability of
SQ109 after administration of prodrug
7a was 91.4% compared with 21.4% after oral administration of
SQ109. After oral administration of compound
7a, the parent drug
SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication.</description><subject>Adamantane - administration & dosage</subject><subject>Adamantane - analogs & derivatives</subject><subject>Adamantane - chemical synthesis</subject><subject>Adamantane - chemistry</subject><subject>Administration, Oral</subject><subject>Animals</subject><subject>Anti-tuberculosis</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antitubercular Agents - administration & dosage</subject><subject>Antitubercular Agents - chemical synthesis</subject><subject>Antitubercular Agents - chemistry</subject><subject>Bioavailability</subject><subject>Biological and medical sciences</subject><subject>Carbamates - administration & dosage</subject><subject>Carbamates - chemical synthesis</subject><subject>Carbamates - chemistry</subject><subject>Ethylenediamines - administration & dosage</subject><subject>Ethylenediamines - chemical synthesis</subject><subject>Ethylenediamines - chemistry</subject><subject>General pharmacology</subject><subject>Medical sciences</subject><subject>Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions</subject><subject>Pharmacology. Drug treatments</subject><subject>Prodrug</subject><subject>Prodrugs - administration & dosage</subject><subject>Prodrugs - chemical synthesis</subject><subject>Prodrugs - chemistry</subject><subject>Rats</subject><subject>SQ109</subject><subject>Tissue Distribution</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>eNqFkE1rFTEUhoMo9lr9Ay5kNrqb8ZxJJrkBN1KqFgrFtkJ3IZM5qbnMR00yhf57Z3ovumtXB8LzvufkYew9QoWA8vOuagfXVzWAroBXoPEF26CQouQCmpdsA1pCudXi5oi9SWkHgAKEeM2OUHNZC4Ubdnn1MObflEIq7NgVdG_72eYwjcXkC2djawebqbiLUxfn27S-Xv1E0IVdAznkuaXo5n56bLilMae37JW3faJ3h3nMfn07vT75UZ5ffD87-XpeOrHFXHqsJSeH3AO3nnfcO6vAOykVdloprxA60EJCvXxji4pz2aimFY2kVknJj9mnfe9y3J-ZUjZDSI763o40zclItZjZ1s2zYA2NROQrWO9BF6eUInlzF8Ng44NBMKtyszOrcrMqN8DNonwJfTi0z-1A3f_IwfECfDwANjnb-2hHF9I_rkahJep1-5c9R4u0-0DRJBdodNSFSC6bbgpP3fEXFIid1w</recordid><startdate>20090515</startdate><enddate>20090515</enddate><creator>Meng, Qingyi</creator><creator>Luo, Huibing</creator><creator>Liu, Yibin</creator><creator>Li, Wei</creator><creator>Zhang, Wen</creator><creator>Yao, Qizheng</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20090515</creationdate><title>Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents</title><author>Meng, Qingyi ; Luo, Huibing ; Liu, Yibin ; Li, Wei ; Zhang, Wen ; Yao, Qizheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c481t-f1263ec13f03af3d3fca70fc6671d977f710d094602960817336575b456eb7663</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Adamantane - administration & dosage</topic><topic>Adamantane - analogs & derivatives</topic><topic>Adamantane - chemical synthesis</topic><topic>Adamantane - chemistry</topic><topic>Administration, Oral</topic><topic>Animals</topic><topic>Anti-tuberculosis</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antitubercular Agents - administration & dosage</topic><topic>Antitubercular Agents - chemical synthesis</topic><topic>Antitubercular Agents - chemistry</topic><topic>Bioavailability</topic><topic>Biological and medical sciences</topic><topic>Carbamates - administration & dosage</topic><topic>Carbamates - chemical synthesis</topic><topic>Carbamates - chemistry</topic><topic>Ethylenediamines - administration & dosage</topic><topic>Ethylenediamines - chemical synthesis</topic><topic>Ethylenediamines - chemistry</topic><topic>General pharmacology</topic><topic>Medical sciences</topic><topic>Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions</topic><topic>Pharmacology. Drug treatments</topic><topic>Prodrug</topic><topic>Prodrugs - administration & dosage</topic><topic>Prodrugs - chemical synthesis</topic><topic>Prodrugs - chemistry</topic><topic>Rats</topic><topic>SQ109</topic><topic>Tissue Distribution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meng, Qingyi</creatorcontrib><creatorcontrib>Luo, Huibing</creatorcontrib><creatorcontrib>Liu, Yibin</creatorcontrib><creatorcontrib>Li, Wei</creatorcontrib><creatorcontrib>Zhang, Wen</creatorcontrib><creatorcontrib>Yao, Qizheng</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</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>Meng, Qingyi</au><au>Luo, Huibing</au><au>Liu, Yibin</au><au>Li, Wei</au><au>Zhang, Wen</au><au>Yao, Qizheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2009-05-15</date><risdate>2009</risdate><volume>19</volume><issue>10</issue><spage>2808</spage><epage>2810</epage><pages>2808-2810</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A new series of carbamate prodrugs of
SQ109 is disclosed. Bioavailability of
SQ109 after administration of prodrug
7a was 91.4% compared with 21.4% after oral administration of
SQ109. After oral administration of compound
7a, the parent drug
SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication.
The low bioavailability of
SQ109 in rats, resulting from first-pass effect in the liver, may be remedied by prodrug strategy. Based on esterase-sensitive carbamate prodrug strategy, a novel series of prodrugs of
SQ109 has been reported. Bioavailability of
SQ109 after administration of prodrug
7a was 91.4% compared with 21.4% after oral administration of
SQ109. After oral administration of compound
7a, the parent drug
SQ109 exhibited preferential tissue distribution into lung and spleen, the target organs of tubercular infection and replication.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19362471</pmid><doi>10.1016/j.bmcl.2009.03.091</doi><tpages>3</tpages></addata></record> |
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subjects | Adamantane - administration & dosage Adamantane - analogs & derivatives Adamantane - chemical synthesis Adamantane - chemistry Administration, Oral Animals Anti-tuberculosis Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Antitubercular Agents - administration & dosage Antitubercular Agents - chemical synthesis Antitubercular Agents - chemistry Bioavailability Biological and medical sciences Carbamates - administration & dosage Carbamates - chemical synthesis Carbamates - chemistry Ethylenediamines - administration & dosage Ethylenediamines - chemical synthesis Ethylenediamines - chemistry General pharmacology Medical sciences Pharmacokinetics. Pharmacogenetics. Drug-receptor interactions Pharmacology. Drug treatments Prodrug Prodrugs - administration & dosage Prodrugs - chemical synthesis Prodrugs - chemistry Rats SQ109 Tissue Distribution |
title | Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents |
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