Publicação
Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons
| Resumo: | The synthesis of 20 arylidenecamphors and 15 pyrimidines with camphane skeleton is described in the current report. A modified method for preparation of sterically hindered 2-aminopyrimidines in two steps was demonstrated. The evaluation of their in vitro activity against Mycobacterium tuberculosis H37Rv showed different MIC values (up to 0.91 μM for ketone 39). Compound 35 demonstrated moderate (8.23 μM), but sustainable activity toward a collection of drug-resistant M. tuberculosis strains. Many of the compounds (especially among 2-aminopyridines 42–56) exhibited good to excellent activity against different strains of pathogenic bacteria and fungi (MIC up to 0.60 μM for compound 50), compared with reference antibiotics. Many of the newly designed compounds possess also in vitro cytotoxicity. |
|---|---|
| Autores principais: | Slavchev, Ivaylo M. |
| Outros Autores: | Mitrev, Yavor; Shivachev, Boris; Valcheva, Violeta; Dogonadze, Marine; Solovieva, Natalia; Vyazovaya, Anna; Mokrousov, Igor; Link, Wolfgang; Jiménez, Lucía; Cautain, Bastien; Mackenzie, Thomas A.; Portugal, Isabel; Lopes, Francisca; Capela, Rita; Perdigão, João; Dobrikov, Georgi M. |
| Assunto: | antibiotics camphor cytotoxicity drug-discovery heterocycles tuberculosi |
| Ano: | 2022 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso restrito |
| Instituição associada: | Universidade de Lisboa |
| Idioma: | inglês |
| Origem: | Repositório da Universidade de Lisboa |
| _version_ | 1866811367717076992 |
|---|---|
| author | Slavchev, Ivaylo M. |
| author2 | Mitrev, Yavor Shivachev, Boris Valcheva, Violeta Dogonadze, Marine Solovieva, Natalia Vyazovaya, Anna Mokrousov, Igor Link, Wolfgang Jiménez, Lucía Cautain, Bastien Mackenzie, Thomas A. Portugal, Isabel Lopes, Francisca Capela, Rita Perdigão, João Dobrikov, Georgi M. |
| author2_role | author author author author author author author author author author author author author author author author |
| author_facet | Slavchev, Ivaylo M. Mitrev, Yavor Shivachev, Boris Valcheva, Violeta Dogonadze, Marine Solovieva, Natalia Vyazovaya, Anna Mokrousov, Igor Link, Wolfgang Jiménez, Lucía Cautain, Bastien Mackenzie, Thomas A. Portugal, Isabel Lopes, Francisca Capela, Rita Perdigão, João Dobrikov, Georgi M. |
| author_role | author |
| contributor_name_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Slavchev, Ivaylo M.\"},{\"Person.name\":\"Mitrev, Yavor\"},{\"Person.name\":\"Shivachev, Boris\"},{\"Person.name\":\"Valcheva, Violeta\"},{\"Person.name\":\"Dogonadze, Marine\"},{\"Person.name\":\"Solovieva, Natalia\"},{\"Person.name\":\"Vyazovaya, Anna\"},{\"Person.name\":\"Mokrousov, Igor\"},{\"Person.name\":\"Link, Wolfgang\"},{\"Person.name\":\"Jiménez, Lucía\"},{\"Person.name\":\"Cautain, Bastien\"},{\"Person.name\":\"Mackenzie, Thomas A.\"},{\"Person.name\":\"Portugal, Isabel\",\"Person.identifier.orcid\":\"0000-0002-7843-0006\"},{\"Person.name\":\"Lopes, Francisca\",\"Person.identifier.orcid\":\"0000-0002-5350-147X\"},{\"Person.name\":\"Capela, Rita\",\"Person.identifier.orcid\":\"0000-0001-9637-3714\"},{\"Person.name\":\"Perdigão, João\",\"Person.identifier.orcid\":\"0000-0002-0339-1305\"},{\"Person.name\":\"Dobrikov, Georgi M.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| datacite.creators.creator.creatorName.fl_str_mv | Slavchev, Ivaylo M. Mitrev, Yavor Shivachev, Boris Valcheva, Violeta Dogonadze, Marine Solovieva, Natalia Vyazovaya, Anna Mokrousov, Igor Link, Wolfgang Jiménez, Lucía Cautain, Bastien Mackenzie, Thomas A. Portugal, Isabel Lopes, Francisca Capela, Rita Perdigão, João Dobrikov, Georgi M. |
| datacite.date.Accepted.fl_str_mv | 2022-05-03T00:00:00Z |
| datacite.date.available.fl_str_mv | 2023-08-18T11:27:17Z |
| datacite.date.embargoed.fl_str_mv | 2023-08-18T11:27:17Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| datacite.subjects.subject.fl_str_mv | antibiotics camphor cytotoxicity drug-discovery heterocycles tuberculosi |
| datacite.titles.title.fl_str_mv | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons |
| dc.contributor.none.fl_str_mv | Repositório Científico de Acesso Aberto da ULisboa |
| dc.creator.none.fl_str_mv | Slavchev, Ivaylo M. Mitrev, Yavor Shivachev, Boris Valcheva, Violeta Dogonadze, Marine Solovieva, Natalia Vyazovaya, Anna Mokrousov, Igor Link, Wolfgang Jiménez, Lucía Cautain, Bastien Mackenzie, Thomas A. Portugal, Isabel Lopes, Francisca Capela, Rita Perdigão, João Dobrikov, Georgi M. |
| dc.date.Accepted.fl_str_mv | 2022-05-03T00:00:00Z |
| dc.date.available.fl_str_mv | 2023-08-18T11:27:17Z |
| dc.date.embargoed.fl_str_mv | 2023-08-18T11:27:17Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10451/58922 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Wiley-VCH |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| dc.subject.none.fl_str_mv | antibiotics camphor cytotoxicity drug-discovery heterocycles tuberculosi |
| dc.title.fl_str_mv | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | The synthesis of 20 arylidenecamphors and 15 pyrimidines with camphane skeleton is described in the current report. A modified method for preparation of sterically hindered 2-aminopyrimidines in two steps was demonstrated. The evaluation of their in vitro activity against Mycobacterium tuberculosis H37Rv showed different MIC values (up to 0.91 μM for ketone 39). Compound 35 demonstrated moderate (8.23 μM), but sustainable activity toward a collection of drug-resistant M. tuberculosis strains. Many of the compounds (especially among 2-aminopyridines 42–56) exhibited good to excellent activity against different strains of pathogenic bacteria and fungi (MIC up to 0.60 μM for compound 50), compared with reference antibiotics. Many of the newly designed compounds possess also in vitro cytotoxicity. |
| dirty | 0 |
| eu_rights_str_mv | restrictedAccess |
| format | article |
| fulltext.url.fl_str_mv | https://repositorio.ulisboa.pt/bitstreams/77716740-37be-4151-948b-ccdc6cdb714e/download |
| id | ul_64bb22a1ea136e6f0e8f620eef0dc277 |
| identifier.url.fl_str_mv | http://hdl.handle.net/10451/58922 |
| instacron_str | ul |
| institution | Universidade de Lisboa |
| instname_str | Universidade de Lisboa |
| language | eng |
| network_acronym_str | ul |
| network_name_str | Repositório da Universidade de Lisboa |
| oai_identifier_str | oai:repositorio.ulisboa.pt:10451/58922 |
| organization_str_mv | urn:organizationAcronym:ul |
| person_str_mv | Slavchev, Ivaylo M. Mitrev, Yavor Shivachev, Boris Valcheva, Violeta Dogonadze, Marine Solovieva, Natalia Vyazovaya, Anna Mokrousov, Igor Link, Wolfgang Jiménez, Lucía Cautain, Bastien Mackenzie, Thomas A. Portugal, Isabel Portugal, Isabel https://www.ciencia-id.pt/E310-5746-C205 E310-5746-C205 http://orcid.org/0000-0002-7843-0006 0000-0002-7843-0006 Lopes, Francisca Lopes, Francisca https://www.ciencia-id.pt/3911-17F9-540E 3911-17F9-540E http://orcid.org/0000-0002-5350-147X 0000-0002-5350-147X Capela, Rita Capela, Rita https://www.ciencia-id.pt/801D-647D-1F16 801D-647D-1F16 http://orcid.org/0000-0001-9637-3714 0000-0001-9637-3714 Perdigão, João Perdigão, João https://www.ciencia-id.pt/991C-F26A-9843 991C-F26A-9843 http://orcid.org/0000-0002-0339-1305 0000-0002-0339-1305 Dobrikov, Georgi M. |
| publishDate | 2022 |
| publisher.none.fl_str_mv | Wiley-VCH |
| reponame_str | Repositório da Universidade de Lisboa |
| repository_id_str | urn:repositoryAcronym:ul |
| service_str_mv | urn:repositoryAcronym:ul |
| spelling | engWiley-VCHpt_PTThe synthesis of 20 arylidenecamphors and 15 pyrimidines with camphane skeleton is described in the current report. A modified method for preparation of sterically hindered 2-aminopyrimidines in two steps was demonstrated. The evaluation of their in vitro activity against Mycobacterium tuberculosis H37Rv showed different MIC values (up to 0.91 μM for ketone 39). Compound 35 demonstrated moderate (8.23 μM), but sustainable activity toward a collection of drug-resistant M. tuberculosis strains. Many of the compounds (especially among 2-aminopyridines 42–56) exhibited good to excellent activity against different strains of pathogenic bacteria and fungi (MIC up to 0.60 μM for compound 50), compared with reference antibiotics. Many of the newly designed compounds possess also in vitro cytotoxicity.application/pdfpt_PTSynthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane SkeletonsSlavchev, Ivaylo M.Mitrev, YavorShivachev, BorisValcheva, VioletaDogonadze, MarineSolovieva, NataliaVyazovaya, AnnaMokrousov, IgorLink, WolfgangJiménez, LucíaCautain, BastienMackenzie, Thomas A.PersonalPortugal, IsabelDSpacehttp://dspace.org/items/4484da69-843c-4a20-af02-b3c111f84324DSpacehttp://dspace.org/items/4484da69-843c-4a20-af02-b3c111f84324PortugalIsabelCiência IDhttps://www.ciencia-id.ptE310-5746-C205ORCIDhttp://orcid.org0000-0002-7843-0006PersonalLopes, FranciscaDSpacehttp://dspace.org/items/914c2246-322f-4b77-85e8-d1e0c22e21d6DSpacehttp://dspace.org/items/914c2246-322f-4b77-85e8-d1e0c22e21d6LopesFranciscaCiência IDhttps://www.ciencia-id.pt3911-17F9-540EORCIDhttp://orcid.org0000-0002-5350-147XPersonalCapela, RitaDSpacehttp://dspace.org/items/5a363f6b-fddd-4922-9b78-b145a1d04903DSpacehttp://dspace.org/items/5a363f6b-fddd-4922-9b78-b145a1d04903CapelaRitaCiência IDhttps://www.ciencia-id.pt801D-647D-1F16ORCIDhttp://orcid.org0000-0001-9637-3714Researcher IDhttps://www.researcherid.comA-6002-2016Scopus Author IDhttps://www.scopus.com6602816287PersonalPerdigão, JoãoDSpacehttp://dspace.org/items/26de40fc-fc1d-4ff9-a242-3bb398e3ac1eDSpacehttp://dspace.org/items/26de40fc-fc1d-4ff9-a242-3bb398e3ac1eLucas Mota PerdigãoJoão RubenCiência IDhttps://www.ciencia-id.pt991C-F26A-9843ORCIDhttp://orcid.org0000-0002-0339-1305Scopus Author IDhttps://www.scopus.com24723211800Dobrikov, Georgi M.HostingInstitutionOrganizationalRepositório Científico de Acesso Aberto da ULisboae-mailmailto:repositorio@reitoria.ulisboa.ptrepositorio@reitoria.ulisboa.ptISSNIsPartOf2365-6549DOIIsPartOf10.1002/slct.2022013392023-08-18T11:27:17Z2022-05-032023-01-04T15:28:02Z2022-05-03T00:00:00ZHandlehttp://hdl.handle.net/10451/58922http://purl.org/coar/access_right/c_16ecrestricted accessantibioticscamphorcytotoxicitydrug-discoveryheterocyclestuberculosi1767273 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_16ecapplication/pdffulltexthttps://repositorio.ulisboa.pt/bitstreams/77716740-37be-4151-948b-ccdc6cdb714e/downloadChemistrySelect717e202201339 |
| spellingShingle | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons Slavchev, Ivaylo M. antibiotics camphor cytotoxicity drug-discovery heterocycles tuberculosi |
| status | SINGLETON |
| subject.fl_str_mv | antibiotics camphor cytotoxicity drug-discovery heterocycles tuberculosi |
| title | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons |
| title_full | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons |
| title_fullStr | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons |
| title_full_unstemmed | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons |
| title_short | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons |
| title_sort | Synthesis, Characterization and Complex Evaluation of Antibacterial Activity and Cytotoxicity of New Arylmethylidene Ketones and Pyrimidines with Camphane Skeletons |
| topic | antibiotics camphor cytotoxicity drug-discovery heterocycles tuberculosi |
| topic_facet | antibiotics camphor cytotoxicity drug-discovery heterocycles tuberculosi |
| url | http://hdl.handle.net/10451/58922 |
| visible | 1 |