Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents
Libraries of 1- and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/ O-methyloximes were synthesized and unambiguously characterized by 1D/2D NMR and single crystal XRD data. All the synthesized oximes and oxime ethers were evaluated for their in vitro antimicrobial activity. Libraries of...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-03, Vol.20 (5), p.1642-1647 |
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| creator | Parthiban, Paramasivam Rathika, Paramasivam Ramkumar, Venkatachalam Son, Se Mo Jeong, Yeon Tae |
| description | Libraries of 1- and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes were synthesized and unambiguously characterized by 1D/2D NMR and single crystal XRD data. All the synthesized oximes and oxime ethers were evaluated for their in vitro antimicrobial activity.
Libraries of 1-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes
1–14/15–28/29–42 and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes
43–48/49–54/55–60 were synthesized and their stereochemistry was established by 1D/2D NMR spectral and single crystal XRD studies. All the synthesized oximes and oxime ethers were screened for their in vitro antimicrobial activity against a panel of pathogenic bacteria (
Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumoniae and
Pseudomonas aeruginosa) and fungi (
Candida albicans, Candida parapsilosis, Aspergillus niger and
Cryptococcus neoformans) using Gentamicin and Fluconazole as standards, respectively. From the SAR profile, the lead molecules were identified. |
| doi_str_mv | 10.1016/j.bmcl.2010.01.048 |
| format | Article |
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O-methyloximes were synthesized and unambiguously characterized by 1D/2D NMR and single crystal XRD data. All the synthesized oximes and oxime ethers were evaluated for their in vitro antimicrobial activity.
Libraries of 1-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes
1–14/15–28/29–42 and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes
43–48/49–54/55–60 were synthesized and their stereochemistry was established by 1D/2D NMR spectral and single crystal XRD studies. All the synthesized oximes and oxime ethers were screened for their in vitro antimicrobial activity against a panel of pathogenic bacteria (
Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumoniae and
Pseudomonas aeruginosa) and fungi (
Candida albicans, Candida parapsilosis, Aspergillus niger and
Cryptococcus neoformans) using Gentamicin and Fluconazole as standards, respectively. From the SAR profile, the lead molecules were identified.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.01.048</identifier><identifier>PMID: 20138517</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>2D NMR ; 3-Azabicyclo[3.3.1]nonan-9-ones ; Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; Antibacterial activity ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antibodies ; Antifungal activity ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Aspergillus niger ; Azabicyclo Compounds - chemical synthesis ; Azabicyclo Compounds - chemistry ; Azabicyclo Compounds - pharmacology ; Biological and medical sciences ; Crystallography, X-Ray ; Ethers - chemistry ; General aspects ; Magnetic Resonance Spectroscopy ; Medical sciences ; Microbial Sensitivity Tests ; Molecular Conformation ; O-Methyloximes ; Oximes ; Oximes - chemistry ; Pharmacology. Drug treatments ; Single crystal XRD ; Small Molecule Libraries ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-03, Vol.20 (5), p.1642-1647</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-c417t-ead4c19f4e6d4caaf2e1e5532656c26a49dc06d5b04f3d8782943b1aca2d63113</citedby><cites>FETCH-LOGICAL-c417t-ead4c19f4e6d4caaf2e1e5532656c26a49dc06d5b04f3d8782943b1aca2d63113</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X10000600$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22824762$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20138517$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Parthiban, Paramasivam</creatorcontrib><creatorcontrib>Rathika, Paramasivam</creatorcontrib><creatorcontrib>Ramkumar, Venkatachalam</creatorcontrib><creatorcontrib>Son, Se Mo</creatorcontrib><creatorcontrib>Jeong, Yeon Tae</creatorcontrib><title>Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Libraries of 1- and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes were synthesized and unambiguously characterized by 1D/2D NMR and single crystal XRD data. All the synthesized oximes and oxime ethers were evaluated for their in vitro antimicrobial activity.
Libraries of 1-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes
1–14/15–28/29–42 and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes
43–48/49–54/55–60 were synthesized and their stereochemistry was established by 1D/2D NMR spectral and single crystal XRD studies. All the synthesized oximes and oxime ethers were screened for their in vitro antimicrobial activity against a panel of pathogenic bacteria (
Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumoniae and
Pseudomonas aeruginosa) and fungi (
Candida albicans, Candida parapsilosis, Aspergillus niger and
Cryptococcus neoformans) using Gentamicin and Fluconazole as standards, respectively. From the SAR profile, the lead molecules were identified.</description><subject>2D NMR</subject><subject>3-Azabicyclo[3.3.1]nonan-9-ones</subject><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>Antibacterial activity</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antibodies</subject><subject>Antifungal activity</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Aspergillus niger</subject><subject>Azabicyclo Compounds - chemical synthesis</subject><subject>Azabicyclo Compounds - chemistry</subject><subject>Azabicyclo Compounds - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Crystallography, X-Ray</subject><subject>Ethers - chemistry</subject><subject>General aspects</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Conformation</subject><subject>O-Methyloximes</subject><subject>Oximes</subject><subject>Oximes - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Single crystal XRD</subject><subject>Small Molecule Libraries</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</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>eNqFkUurFDEQRoMo3vHqH3Ah2YirHvPqdLe4GS6-4ILgVXAXqpNqzdCPMZVRx19vxhl1p6sUqfMVlRzGHkqxlkLap9t1P_lxrUS5EHItTHuLraSxptJG1LfZSnRWVG1nPl6we0RbIaQRxtxlFyWi21o2KzbfZEy40A59HKLndJjzZ6RIfBn48j1OSBzmcCo5ll761dIV_IA--oMfkZ7xDb_ZvOOU9-HA8_INUjjGcpyiT0sfYeTwCedM99mdAUbCB-fzkn14-eL91evq-u2rN1eb68ob2eQKIRgvu8GgLQXAoFBiXWtla-uVBdMFL2yoe2EGHdqmVZ3RvQQPKlgtpb5kT05zd2n5skfKborkcRxhxmVPrjG11bUW5v-k1qK1Xd0UUp3I8iSihIPbpThBOjgp3FGI27qjEHcU4oR0RUgJPTqP3_cThj-R3wYK8PgMAHkYhwSzj_SXU60yjVWFe37isHzb14jJkY84ewwxoc8uLPFfe_wEtJ2qAQ</recordid><startdate>20100301</startdate><enddate>20100301</enddate><creator>Parthiban, Paramasivam</creator><creator>Rathika, Paramasivam</creator><creator>Ramkumar, Venkatachalam</creator><creator>Son, Se Mo</creator><creator>Jeong, Yeon Tae</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><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>20100301</creationdate><title>Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents</title><author>Parthiban, Paramasivam ; Rathika, Paramasivam ; Ramkumar, Venkatachalam ; Son, Se Mo ; Jeong, Yeon Tae</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-ead4c19f4e6d4caaf2e1e5532656c26a49dc06d5b04f3d8782943b1aca2d63113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>2D NMR</topic><topic>3-Azabicyclo[3.3.1]nonan-9-ones</topic><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>Antibacterial activity</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antibodies</topic><topic>Antifungal activity</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Aspergillus niger</topic><topic>Azabicyclo Compounds - chemical synthesis</topic><topic>Azabicyclo Compounds - chemistry</topic><topic>Azabicyclo Compounds - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Crystallography, X-Ray</topic><topic>Ethers - chemistry</topic><topic>General aspects</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Conformation</topic><topic>O-Methyloximes</topic><topic>Oximes</topic><topic>Oximes - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Single crystal XRD</topic><topic>Small Molecule Libraries</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Parthiban, Paramasivam</creatorcontrib><creatorcontrib>Rathika, Paramasivam</creatorcontrib><creatorcontrib>Ramkumar, Venkatachalam</creatorcontrib><creatorcontrib>Son, Se Mo</creatorcontrib><creatorcontrib>Jeong, Yeon Tae</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><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Parthiban, Paramasivam</au><au>Rathika, Paramasivam</au><au>Ramkumar, Venkatachalam</au><au>Son, Se Mo</au><au>Jeong, Yeon Tae</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010-03-01</date><risdate>2010</risdate><volume>20</volume><issue>5</issue><spage>1642</spage><epage>1647</epage><pages>1642-1647</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Libraries of 1- and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes were synthesized and unambiguously characterized by 1D/2D NMR and single crystal XRD data. All the synthesized oximes and oxime ethers were evaluated for their in vitro antimicrobial activity.
Libraries of 1-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes
1–14/15–28/29–42 and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/
O-methyloximes
43–48/49–54/55–60 were synthesized and their stereochemistry was established by 1D/2D NMR spectral and single crystal XRD studies. All the synthesized oximes and oxime ethers were screened for their in vitro antimicrobial activity against a panel of pathogenic bacteria (
Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumoniae and
Pseudomonas aeruginosa) and fungi (
Candida albicans, Candida parapsilosis, Aspergillus niger and
Cryptococcus neoformans) using Gentamicin and Fluconazole as standards, respectively. From the SAR profile, the lead molecules were identified.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20138517</pmid><doi>10.1016/j.bmcl.2010.01.048</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2010-03, Vol.20 (5), p.1642-1647 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | 2D NMR 3-Azabicyclo[3.3.1]nonan-9-ones Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology Antibacterial activity Antibiotics. Antiinfectious agents. Antiparasitic agents Antibodies Antifungal activity Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Aspergillus niger Azabicyclo Compounds - chemical synthesis Azabicyclo Compounds - chemistry Azabicyclo Compounds - pharmacology Biological and medical sciences Crystallography, X-Ray Ethers - chemistry General aspects Magnetic Resonance Spectroscopy Medical sciences Microbial Sensitivity Tests Molecular Conformation O-Methyloximes Oximes Oximes - chemistry Pharmacology. Drug treatments Single crystal XRD Small Molecule Libraries Stereoisomerism Structure-Activity Relationship |
| title | Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents |
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