Publicação
2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B
| Resumo: | Crystallography shows that the Te atom in each of (p-tol)Te[C(H)=C(Cl)Ph]X2, for X = Cl (1), Br (2) and I (3), is within a distorted Ψ-pentagonal bipyramidal geometry. An E configuration for the vinyl group in (1) precludes the formation of an intramolecular Te···Cl interaction so that an intramolecular Te···π interaction is found instead. The coordination environment features a linear Cl-Te-Cl arrangement with the pentagonal plane defined by the two C atoms of the organic substituents, an intermolecular Te···Cl contact, a Te···π interaction and a stereochemically active lone pair of electrons. In the X = Br (2) and I (3) structures, similar coordination geometries are found but the Te···π contact is replaced by an intramolecular Te···Cl contact owing to the adoption of a Z configuration about the vinyl bond. The differences in structure are readily explained in terms of electronic effects. Docking studies of cathepsin B with (1')-(3'), i.e. 1-3 less one Te-bound halide, show efficient binding through the agency of covalent Te-S Cys29 bonds with stabilization afforded by a combination of N-H···π, C-H···π and Cl vinyl···H interactions. These results comparable favorably with known inhibitors of cathepsin B suggesting the title compounds have potential biological activity. |
|---|---|
| Autores principais: | Caracelli,Ignez |
| Outros Autores: | Zukerman-Schpector,Julio; Maganhi,Stella H; Stefani,Hélio A; Guadagnin,Rafael; Tiekink,Edward R. T |
| Assunto: | organotellurium-dihalides docking studies cathepsin B crystal structures supramolecular arrangements |
| Ano: | 2010 |
| País: | Brasil |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | IBICT |
| Idioma: | inglês |
| Origem: | Oasisbr |
| _version_ | 1871506605621641216 |
|---|---|
| author | Caracelli,Ignez |
| author2 | Zukerman-Schpector,Julio Maganhi,Stella H Stefani,Hélio A Guadagnin,Rafael Tiekink,Edward R. T |
| author2_role | author author author author author |
| author_facet | Caracelli,Ignez Zukerman-Schpector,Julio Maganhi,Stella H Stefani,Hélio A Guadagnin,Rafael Tiekink,Edward R. T |
| author_role | author |
| country_str | BR |
| creators_json_txt | [{\"Person.name\":\"Caracelli,Ignez\"},{\"Person.name\":\"Zukerman-Schpector,Julio\"},{\"Person.name\":\"Maganhi,Stella H\"},{\"Person.name\":\"Stefani,Hélio A\"},{\"Person.name\":\"Guadagnin,Rafael\"},{\"Person.name\":\"Tiekink,Edward R. T\"}] |
| datacite.creators.creator.creatorName.fl_str_mv | Caracelli,Ignez Zukerman-Schpector,Julio Maganhi,Stella H Stefani,Hélio A Guadagnin,Rafael Tiekink,Edward R. T |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | organotellurium-dihalides docking studies cathepsin B crystal structures supramolecular arrangements |
| datacite.titles.title.fl_str_mv | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B |
| dc.creator.none.fl_str_mv | Caracelli,Ignez Zukerman-Schpector,Julio Maganhi,Stella H Stefani,Hélio A Guadagnin,Rafael Tiekink,Edward R. T |
| dc.format.none.fl_str_mv | text/html |
| dc.identifier.none.fl_str_mv | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100018 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Sociedade Brasileira de Química |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.source.none.fl_str_mv | Journal of the Brazilian Chemical Society v.21 n.11 2010 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
| dc.subject.none.fl_str_mv | organotellurium-dihalides docking studies cathepsin B crystal structures supramolecular arrangements |
| dc.title.fl_str_mv | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | Crystallography shows that the Te atom in each of (p-tol)Te[C(H)=C(Cl)Ph]X2, for X = Cl (1), Br (2) and I (3), is within a distorted Ψ-pentagonal bipyramidal geometry. An E configuration for the vinyl group in (1) precludes the formation of an intramolecular Te···Cl interaction so that an intramolecular Te···π interaction is found instead. The coordination environment features a linear Cl-Te-Cl arrangement with the pentagonal plane defined by the two C atoms of the organic substituents, an intermolecular Te···Cl contact, a Te···π interaction and a stereochemically active lone pair of electrons. In the X = Br (2) and I (3) structures, similar coordination geometries are found but the Te···π contact is replaced by an intramolecular Te···Cl contact owing to the adoption of a Z configuration about the vinyl bond. The differences in structure are readily explained in terms of electronic effects. Docking studies of cathepsin B with (1')-(3'), i.e. 1-3 less one Te-bound halide, show efficient binding through the agency of covalent Te-S Cys29 bonds with stabilization afforded by a combination of N-H···π, C-H···π and Cl vinyl···H interactions. These results comparable favorably with known inhibitors of cathepsin B suggesting the title compounds have potential biological activity. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| id | oasisbr_b996bd2efa5ac8b4e4ed55dcb819bcfe |
| identifier.url.fl_str_mv | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100018 |
| inst_facet_str | urn:organizationAcronym:oasisbr{{{_:::_}}}IBICT |
| instacron_str | OASISBR |
| institution | IBICT |
| instname_str | IBICT |
| language | eng |
| network_acronym_str | oasisbr |
| network_name_str | Oasisbr |
| oai_identifier_str | oai:scielo:S0103-50532010001100018 |
| organization_str_mv | urn:organizationAcronym:oasisbr |
| person_str_mv | Caracelli,Ignez Zukerman-Schpector,Julio Maganhi,Stella H Stefani,Hélio A Guadagnin,Rafael Tiekink,Edward R. T |
| publishDate | 2010 |
| publisher.none.fl_str_mv | Sociedade Brasileira de Química |
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| reponame_str | Oasisbr |
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| spelling | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin BCaracelli,IgnezZukerman-Schpector,JulioMaganhi,Stella HStefani,Hélio AGuadagnin,RafaelTiekink,Edward R. Torganotellurium-dihalidesdocking studiescathepsin Bcrystal structuressupramolecular arrangementsopen accesshttp://purl.org/coar/access_right/c_abf2http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100018URLhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100018URLHasVersion2010-01-01Crystallography shows that the Te atom in each of (p-tol)Te[C(H)=C(Cl)Ph]X2, for X = Cl (1), Br (2) and I (3), is within a distorted Ψ-pentagonal bipyramidal geometry. An E configuration for the vinyl group in (1) precludes the formation of an intramolecular Te···Cl interaction so that an intramolecular Te···π interaction is found instead. The coordination environment features a linear Cl-Te-Cl arrangement with the pentagonal plane defined by the two C atoms of the organic substituents, an intermolecular Te···Cl contact, a Te···π interaction and a stereochemically active lone pair of electrons. In the X = Br (2) and I (3) structures, similar coordination geometries are found but the Te···π contact is replaced by an intramolecular Te···Cl contact owing to the adoption of a Z configuration about the vinyl bond. The differences in structure are readily explained in terms of electronic effects. Docking studies of cathepsin B with (1')-(3'), i.e. 1-3 less one Te-bound halide, show efficient binding through the agency of covalent Te-S Cys29 bonds with stabilization afforded by a combination of N-H···π, C-H···π and Cl vinyl···H interactions. These results comparable favorably with known inhibitors of cathepsin B suggesting the title compounds have potential biological activity.engtext/htmlSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.21 n.11 2010reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQjournal articlehttp://purl.org/coar/resource_type/c_6501literatureVoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85 |
| spellingShingle | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B Caracelli,Ignez organotellurium-dihalides docking studies cathepsin B crystal structures supramolecular arrangements |
| status | SINGLETON |
| status_str | VoR |
| subject.fl_str_mv | organotellurium-dihalides docking studies cathepsin B crystal structures supramolecular arrangements |
| title | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B |
| title_full | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B |
| title_fullStr | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B |
| title_full_unstemmed | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B |
| title_short | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B |
| title_sort | 2-chlorovinyl tellurium dihalides, (p-tol)Te[C(H)=C(Cl)Ph]X2 for X = Cl, Br and I: variable coordination environments, supramolecular structures and docking studies in cathepsin B |
| topic | organotellurium-dihalides docking studies cathepsin B crystal structures supramolecular arrangements |
| topic_facet | organotellurium-dihalides docking studies cathepsin B crystal structures supramolecular arrangements |
| url | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010001100018 |
| visible | 1 |
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