Functionalised bicyclic tetramates derived from cysteine as antibacterial agents.
Routes to bicyclic tetramates derived from cysteine permitting ready incorporation of functionality at two different points around the periphery of a heterocyclic skeleton are reported. This has enabled the identification of systems active against Gram-positive bacteria, some of which show gyrase an...
| Asıl Yazarlar: | , , , , , , , , , , |
|---|---|
| Materyal Türü: | Journal article |
| Dil: | English |
| Baskı/Yayın Bilgisi: |
Royal Society of Chemistry
2019
|
| _version_ | 1826304482733981696 |
|---|---|
| author | Panduwawala, TD Iqbal, S Thompson, AL Genov, M Pretsch, A Pretsch, D Liu, S Ebright, RH Howells, A Maxwell, A Moloney, MG |
| author_facet | Panduwawala, TD Iqbal, S Thompson, AL Genov, M Pretsch, A Pretsch, D Liu, S Ebright, RH Howells, A Maxwell, A Moloney, MG |
| author_sort | Panduwawala, TD |
| collection | OXFORD |
| description | Routes to bicyclic tetramates derived from cysteine permitting ready incorporation of functionality at two different points around the periphery of a heterocyclic skeleton are reported. This has enabled the identification of systems active against Gram-positive bacteria, some of which show gyrase and RNA polymerase inhibitory activity. In particular, tetramates substituted with glycosyl side chains, chosen to impart polarity and aqueous solubility, show high antibacterial activity coupled with modest gyrase/polymerase activity in two cases. An analysis of physicochemical properties indicates that the antibacterially active tetramates generally occupy physicochemical space with MW of 300-600, clog D7.4 of -2.5 to 4 and rel. PSA of 11-22%. This work demonstrates that biologically active 3D libraries are readily available by manipulation of a tetramate skeleton. |
| first_indexed | 2024-03-07T06:18:29Z |
| format | Journal article |
| id | oxford-uuid:f1e62e05-83a1-4dd3-9d13-f7fb95be0a55 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:18:29Z |
| publishDate | 2019 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:f1e62e05-83a1-4dd3-9d13-f7fb95be0a552022-03-27T11:59:31ZFunctionalised bicyclic tetramates derived from cysteine as antibacterial agents.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:f1e62e05-83a1-4dd3-9d13-f7fb95be0a55EnglishSymplectic Elements at OxfordRoyal Society of Chemistry2019Panduwawala, TDIqbal, SThompson, ALGenov, MPretsch, APretsch, DLiu, SEbright, RHHowells, AMaxwell, AMoloney, MGRoutes to bicyclic tetramates derived from cysteine permitting ready incorporation of functionality at two different points around the periphery of a heterocyclic skeleton are reported. This has enabled the identification of systems active against Gram-positive bacteria, some of which show gyrase and RNA polymerase inhibitory activity. In particular, tetramates substituted with glycosyl side chains, chosen to impart polarity and aqueous solubility, show high antibacterial activity coupled with modest gyrase/polymerase activity in two cases. An analysis of physicochemical properties indicates that the antibacterially active tetramates generally occupy physicochemical space with MW of 300-600, clog D7.4 of -2.5 to 4 and rel. PSA of 11-22%. This work demonstrates that biologically active 3D libraries are readily available by manipulation of a tetramate skeleton. |
| spellingShingle | Panduwawala, TD Iqbal, S Thompson, AL Genov, M Pretsch, A Pretsch, D Liu, S Ebright, RH Howells, A Maxwell, A Moloney, MG Functionalised bicyclic tetramates derived from cysteine as antibacterial agents. |
| title | Functionalised bicyclic tetramates derived from cysteine as antibacterial agents. |
| title_full | Functionalised bicyclic tetramates derived from cysteine as antibacterial agents. |
| title_fullStr | Functionalised bicyclic tetramates derived from cysteine as antibacterial agents. |
| title_full_unstemmed | Functionalised bicyclic tetramates derived from cysteine as antibacterial agents. |
| title_short | Functionalised bicyclic tetramates derived from cysteine as antibacterial agents. |
| title_sort | functionalised bicyclic tetramates derived from cysteine as antibacterial agents |
| work_keys_str_mv | AT panduwawalatd functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT iqbals functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT thompsonal functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT genovm functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT pretscha functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT pretschd functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT lius functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT ebrightrh functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT howellsa functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT maxwella functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents AT moloneymg functionalisedbicyclictetramatesderivedfromcysteineasantibacterialagents |