Synthesis and in Vitro Evaluation of the Antitubercular and Antibacterial Activity of Novel Oxazolidinones Bearing Octahydrocyclopenta[c]pyrrol-2-yl Moieties
A novel series of oxazolidinone-class antimicrobial agents with 5-substituted octahydrocyclopenta[c]pyrrole moieties at the C-ring of linezolid and an acetamide or 1,2,3-triazole ring as the C-5 side chain of the oxazolidinone ring were prepared. The resulting series of compounds were evaluated for...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2014/12/01, Vol.62(12), pp.1214-1224 |
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| creator | Bhattarai, Deepak Lee, Ju-hyeon Seo, Seon Hee Nam, Ghilsoo Choo, Hyunah Kang, Soon Bang Kwak, Jin-Hwan Oh, Taegwon Cho, Sang-Nae Pae, Ae Nim Kim, Eunice Eunkyeong Jeong, Nakcheol Keum, Gyochang |
| description | A novel series of oxazolidinone-class antimicrobial agents with 5-substituted octahydrocyclopenta[c]pyrrole moieties at the C-ring of linezolid and an acetamide or 1,2,3-triazole ring as the C-5 side chain of the oxazolidinone ring were prepared. The resulting series of compounds were evaluated for in vitro antimicrobial activity against Mycobacterium tuberculosis and a panel of clinically important resistant Gram-positive and -negative bacteria. Among them, endo-alcohol 2a and exo-alcohol 2b showed potent inhibitory activity against M. tuberculosis H37Rv, which was superior to that of linezolid. Several analogues in this series showed potent in vitro antibacterial activity against the clinically important vancomycin-resistant bacteria and showed similar or better potency against linezolid-resistant methicillin-resistant Staphylococcus aureus (MRSA) strains. The hydroxyl group in the azabicyclic C-ring interacted with the same hydrophobic pocket as linezolid based on a docking study. Selected compounds with high antimicrobial activity showed good human microsomal stability and low CYP isozyme and monoamine oxidase (MAO) inhibition. |
| doi_str_mv | 10.1248/cpb.c14-00510 |
| format | Article |
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The resulting series of compounds were evaluated for in vitro antimicrobial activity against Mycobacterium tuberculosis and a panel of clinically important resistant Gram-positive and -negative bacteria. Among them, endo-alcohol 2a and exo-alcohol 2b showed potent inhibitory activity against M. tuberculosis H37Rv, which was superior to that of linezolid. Several analogues in this series showed potent in vitro antibacterial activity against the clinically important vancomycin-resistant bacteria and showed similar or better potency against linezolid-resistant methicillin-resistant Staphylococcus aureus (MRSA) strains. The hydroxyl group in the azabicyclic C-ring interacted with the same hydrophobic pocket as linezolid based on a docking study. Selected compounds with high antimicrobial activity showed good human microsomal stability and low CYP isozyme and monoamine oxidase (MAO) inhibition.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.c14-00510</identifier><identifier>PMID: 25297523</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - pharmacology ; antibacterial agent ; Antitubercular Agents - chemical synthesis ; Antitubercular Agents - pharmacology ; Azabicyclo Compounds - chemical synthesis ; Azabicyclo Compounds - pharmacology ; Cytochrome P-450 Enzyme Inhibitors - pharmacology ; Enzyme Inhibitors - pharmacology ; Gram-Negative Bacteria - drug effects ; Gram-positive bacteria ; Gram-Positive Bacteria - drug effects ; High-Throughput Screening Assays ; linezolid ; Methicillin-Resistant Staphylococcus aureus - drug effects ; Microbial Sensitivity Tests ; Models, Molecular ; Monoamine Oxidase Inhibitors - pharmacology ; Mycobacterium tuberculosis ; Mycobacterium tuberculosis - drug effects ; Oxazoles - chemical synthesis ; Oxazoles - pharmacology ; oxazolidinone ; Pyrrolidines - chemical synthesis ; Pyrrolidines - pharmacology ; Staphylococcus aureus ; Vancomycin Resistance</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2014/12/01, Vol.62(12), pp.1214-1224</ispartof><rights>2014 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2014</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c736t-339c4269ebe416849222ba4043462d045f52cb8f9ee7221ee5f9282c8509b1a93</citedby><cites>FETCH-LOGICAL-c736t-339c4269ebe416849222ba4043462d045f52cb8f9ee7221ee5f9282c8509b1a93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1876,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25297523$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bhattarai, Deepak</creatorcontrib><creatorcontrib>Lee, Ju-hyeon</creatorcontrib><creatorcontrib>Seo, Seon Hee</creatorcontrib><creatorcontrib>Nam, Ghilsoo</creatorcontrib><creatorcontrib>Choo, Hyunah</creatorcontrib><creatorcontrib>Kang, Soon Bang</creatorcontrib><creatorcontrib>Kwak, Jin-Hwan</creatorcontrib><creatorcontrib>Oh, Taegwon</creatorcontrib><creatorcontrib>Cho, Sang-Nae</creatorcontrib><creatorcontrib>Pae, Ae Nim</creatorcontrib><creatorcontrib>Kim, Eunice Eunkyeong</creatorcontrib><creatorcontrib>Jeong, Nakcheol</creatorcontrib><creatorcontrib>Keum, Gyochang</creatorcontrib><creatorcontrib>Korea University</creatorcontrib><creatorcontrib>Handong Global University</creatorcontrib><creatorcontrib>Department of Biological Chemistry</creatorcontrib><creatorcontrib>University of Science and Technology</creatorcontrib><creatorcontrib>Department of chemistry</creatorcontrib><creatorcontrib>Department of Microbiology and the Brain Korea Project for the Medical Sciences</creatorcontrib><creatorcontrib>Korea Institute of Science and Technology(KIST</creatorcontrib><creatorcontrib>Yonsei University College of Medicine</creatorcontrib><creatorcontrib>Brain Science Institute</creatorcontrib><creatorcontrib>School of Life Science</creatorcontrib><creatorcontrib>Center for Neuro-Medicine</creatorcontrib><title>Synthesis and in Vitro Evaluation of the Antitubercular and Antibacterial Activity of Novel Oxazolidinones Bearing Octahydrocyclopenta[c]pyrrol-2-yl Moieties</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>A novel series of oxazolidinone-class antimicrobial agents with 5-substituted octahydrocyclopenta[c]pyrrole moieties at the C-ring of linezolid and an acetamide or 1,2,3-triazole ring as the C-5 side chain of the oxazolidinone ring were prepared. The resulting series of compounds were evaluated for in vitro antimicrobial activity against Mycobacterium tuberculosis and a panel of clinically important resistant Gram-positive and -negative bacteria. Among them, endo-alcohol 2a and exo-alcohol 2b showed potent inhibitory activity against M. tuberculosis H37Rv, which was superior to that of linezolid. Several analogues in this series showed potent in vitro antibacterial activity against the clinically important vancomycin-resistant bacteria and showed similar or better potency against linezolid-resistant methicillin-resistant Staphylococcus aureus (MRSA) strains. The hydroxyl group in the azabicyclic C-ring interacted with the same hydrophobic pocket as linezolid based on a docking study. Selected compounds with high antimicrobial activity showed good human microsomal stability and low CYP isozyme and monoamine oxidase (MAO) inhibition.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>antibacterial agent</subject><subject>Antitubercular Agents - chemical synthesis</subject><subject>Antitubercular Agents - pharmacology</subject><subject>Azabicyclo Compounds - chemical synthesis</subject><subject>Azabicyclo Compounds - pharmacology</subject><subject>Cytochrome P-450 Enzyme Inhibitors - pharmacology</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Gram-Negative Bacteria - drug effects</subject><subject>Gram-positive bacteria</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>High-Throughput Screening Assays</subject><subject>linezolid</subject><subject>Methicillin-Resistant Staphylococcus aureus - drug effects</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Monoamine Oxidase Inhibitors - pharmacology</subject><subject>Mycobacterium tuberculosis</subject><subject>Mycobacterium tuberculosis - drug effects</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - pharmacology</subject><subject>oxazolidinone</subject><subject>Pyrrolidines - chemical synthesis</subject><subject>Pyrrolidines - pharmacology</subject><subject>Staphylococcus aureus</subject><subject>Vancomycin Resistance</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkk9vEzEQxVcIREvhyBVZ4sJliz327sbHUEpBKuTAnwtCK68z2zhy7NT2Rizfhe-KNympxIWLR_b8_OZZz0XxnNFzBmL2Wm-7c81ESWnF6IPilHHRlBUAf1icUkplCbzmJ8WTGNeUQkUb_rg4gQpkUwE_LX5_Hl1aYTSRKLckxpFvJgVPLnfKDioZ74jvSSbI3CWThg6DHqwKe3o66pROGIyyZK6T2Zk0Thc--R1asvipfnlrlsZ5h5G8QRWMuyELndRqXAavR239Fl1S3_WP7RiCtyWUoyUfvcFkMD4tHvXKRnx2V8-Kr-8uv1y8L68XVx8u5telbnidSs6lFlBL7FCweiYkAHRKUMFFDUsqqr4C3c16idgAMMSqlzADPauo7JiS_Kx4ddDdBn87YEztxkSN1iqHfogta2rgVS1Y9X-0BikbUXPI6Mt_0LUfgssPyYIVlwyym0yVB0oHH2PAvt0Gs1FhbBltp4jbHHGbI273EWf-xZ3q0G1weaT_ZpqBqwOQu0Yr6501Du9n69joFW5MC3QvWgODXGZ5WN4zADF9mYZN1t4elNYxqRs8jlIhGW1xb6yGfGVajw7v2ysVWnT8DzxN0as</recordid><startdate>20141201</startdate><enddate>20141201</enddate><creator>Bhattarai, Deepak</creator><creator>Lee, Ju-hyeon</creator><creator>Seo, Seon Hee</creator><creator>Nam, Ghilsoo</creator><creator>Choo, Hyunah</creator><creator>Kang, Soon Bang</creator><creator>Kwak, Jin-Hwan</creator><creator>Oh, Taegwon</creator><creator>Cho, Sang-Nae</creator><creator>Pae, Ae Nim</creator><creator>Kim, Eunice Eunkyeong</creator><creator>Jeong, Nakcheol</creator><creator>Keum, Gyochang</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</general><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope><scope>7QL</scope><scope>C1K</scope></search><sort><creationdate>20141201</creationdate><title>Synthesis and in Vitro Evaluation of the Antitubercular and Antibacterial Activity of Novel Oxazolidinones Bearing Octahydrocyclopenta[c]pyrrol-2-yl Moieties</title><author>Bhattarai, Deepak ; Lee, Ju-hyeon ; Seo, Seon Hee ; Nam, Ghilsoo ; Choo, Hyunah ; Kang, Soon Bang ; Kwak, Jin-Hwan ; Oh, Taegwon ; Cho, Sang-Nae ; Pae, Ae Nim ; Kim, Eunice Eunkyeong ; Jeong, Nakcheol ; Keum, Gyochang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c736t-339c4269ebe416849222ba4043462d045f52cb8f9ee7221ee5f9282c8509b1a93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>antibacterial agent</topic><topic>Antitubercular Agents - chemical synthesis</topic><topic>Antitubercular Agents - pharmacology</topic><topic>Azabicyclo Compounds - chemical synthesis</topic><topic>Azabicyclo Compounds - pharmacology</topic><topic>Cytochrome P-450 Enzyme Inhibitors - pharmacology</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Gram-Negative Bacteria - drug effects</topic><topic>Gram-positive bacteria</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>High-Throughput Screening Assays</topic><topic>linezolid</topic><topic>Methicillin-Resistant Staphylococcus aureus - drug effects</topic><topic>Microbial Sensitivity Tests</topic><topic>Models, Molecular</topic><topic>Monoamine Oxidase Inhibitors - pharmacology</topic><topic>Mycobacterium tuberculosis</topic><topic>Mycobacterium tuberculosis - drug effects</topic><topic>Oxazoles - chemical synthesis</topic><topic>Oxazoles - pharmacology</topic><topic>oxazolidinone</topic><topic>Pyrrolidines - chemical synthesis</topic><topic>Pyrrolidines - pharmacology</topic><topic>Staphylococcus aureus</topic><topic>Vancomycin Resistance</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bhattarai, Deepak</creatorcontrib><creatorcontrib>Lee, Ju-hyeon</creatorcontrib><creatorcontrib>Seo, Seon Hee</creatorcontrib><creatorcontrib>Nam, Ghilsoo</creatorcontrib><creatorcontrib>Choo, Hyunah</creatorcontrib><creatorcontrib>Kang, Soon Bang</creatorcontrib><creatorcontrib>Kwak, Jin-Hwan</creatorcontrib><creatorcontrib>Oh, Taegwon</creatorcontrib><creatorcontrib>Cho, Sang-Nae</creatorcontrib><creatorcontrib>Pae, Ae Nim</creatorcontrib><creatorcontrib>Kim, Eunice Eunkyeong</creatorcontrib><creatorcontrib>Jeong, Nakcheol</creatorcontrib><creatorcontrib>Keum, Gyochang</creatorcontrib><creatorcontrib>Korea University</creatorcontrib><creatorcontrib>Handong Global University</creatorcontrib><creatorcontrib>Department of Biological Chemistry</creatorcontrib><creatorcontrib>University of Science and Technology</creatorcontrib><creatorcontrib>Department of chemistry</creatorcontrib><creatorcontrib>Department of Microbiology and the Brain Korea Project for the Medical Sciences</creatorcontrib><creatorcontrib>Korea Institute of Science and Technology(KIST</creatorcontrib><creatorcontrib>Yonsei University College of Medicine</creatorcontrib><creatorcontrib>Brain Science Institute</creatorcontrib><creatorcontrib>School of Life Science</creatorcontrib><creatorcontrib>Center for Neuro-Medicine</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - 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Pharm. Bull.</addtitle><date>2014-12-01</date><risdate>2014</risdate><volume>62</volume><issue>12</issue><spage>1214</spage><epage>1224</epage><pages>1214-1224</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>A novel series of oxazolidinone-class antimicrobial agents with 5-substituted octahydrocyclopenta[c]pyrrole moieties at the C-ring of linezolid and an acetamide or 1,2,3-triazole ring as the C-5 side chain of the oxazolidinone ring were prepared. The resulting series of compounds were evaluated for in vitro antimicrobial activity against Mycobacterium tuberculosis and a panel of clinically important resistant Gram-positive and -negative bacteria. Among them, endo-alcohol 2a and exo-alcohol 2b showed potent inhibitory activity against M. tuberculosis H37Rv, which was superior to that of linezolid. Several analogues in this series showed potent in vitro antibacterial activity against the clinically important vancomycin-resistant bacteria and showed similar or better potency against linezolid-resistant methicillin-resistant Staphylococcus aureus (MRSA) strains. The hydroxyl group in the azabicyclic C-ring interacted with the same hydrophobic pocket as linezolid based on a docking study. Selected compounds with high antimicrobial activity showed good human microsomal stability and low CYP isozyme and monoamine oxidase (MAO) inhibition.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>25297523</pmid><doi>10.1248/cpb.c14-00510</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 2014/12/01, Vol.62(12), pp.1214-1224 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology antibacterial agent Antitubercular Agents - chemical synthesis Antitubercular Agents - pharmacology Azabicyclo Compounds - chemical synthesis Azabicyclo Compounds - pharmacology Cytochrome P-450 Enzyme Inhibitors - pharmacology Enzyme Inhibitors - pharmacology Gram-Negative Bacteria - drug effects Gram-positive bacteria Gram-Positive Bacteria - drug effects High-Throughput Screening Assays linezolid Methicillin-Resistant Staphylococcus aureus - drug effects Microbial Sensitivity Tests Models, Molecular Monoamine Oxidase Inhibitors - pharmacology Mycobacterium tuberculosis Mycobacterium tuberculosis - drug effects Oxazoles - chemical synthesis Oxazoles - pharmacology oxazolidinone Pyrrolidines - chemical synthesis Pyrrolidines - pharmacology Staphylococcus aureus Vancomycin Resistance |
| title | Synthesis and in Vitro Evaluation of the Antitubercular and Antibacterial Activity of Novel Oxazolidinones Bearing Octahydrocyclopenta[c]pyrrol-2-yl Moieties |
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