Synthesis, anti-tuberculosis activity and QSAR study of 2,4-diarylquinolines and analogous polycyclic derivatives
The multicomponent syntheses of 2,4-di-aryl-quinolines and analogous polycyclic derivatives as anti-tuberculosis agents were described. They were prepared via Beyer and Friedländer methods under microwave irradiation in short reaction times and good yields. Several homogeneous and heterogeneous acid...
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| Format: | Article |
| Language: | English |
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Elsevier
2019-11-01
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| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535218302053 |
| _version_ | 1818538679021338624 |
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| author | Gisela C. Muscia Juan P. Carnevale Ayelen Luczywo María Victoria Peláez Ailen Rodríguez Ó Toole Graciela Y. Buldain Juan J. Casal Silvia E. Asís |
| author_facet | Gisela C. Muscia Juan P. Carnevale Ayelen Luczywo María Victoria Peláez Ailen Rodríguez Ó Toole Graciela Y. Buldain Juan J. Casal Silvia E. Asís |
| author_sort | Gisela C. Muscia |
| collection | DOAJ |
| description | The multicomponent syntheses of 2,4-di-aryl-quinolines and analogous polycyclic derivatives as anti-tuberculosis agents were described. They were prepared via Beyer and Friedländer methods under microwave irradiation in short reaction times and good yields. Several homogeneous and heterogeneous acid catalysts were compared for preparing 2,4-di-arylquinolines and among them trifluoroacetic acid (TFA) reached the higher yields. Two derivatives exhibited activity against Mycobacterium tuberculosis H37Rv (Mtb), underwent additional testing and were considered lead compounds. The synthesis of a series of polycyclic analogous led to six new active compounds and a Quantitative Structure Activity Relationship study (QSAR) study was established. Keywords: Substituted quinolines, DARQ, Microwave-assisted synthesis, Catalysis, Mycobacterium tuberculosis, QSAR |
| first_indexed | 2024-12-11T21:32:04Z |
| format | Article |
| id | doaj.art-4bf9f9e9a2c94aeab0f74c80e9f185c8 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-11T21:32:04Z |
| publishDate | 2019-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-4bf9f9e9a2c94aeab0f74c80e9f185c82022-12-22T00:50:08ZengElsevierArabian Journal of Chemistry1878-53522019-11-01127932945Synthesis, anti-tuberculosis activity and QSAR study of 2,4-diarylquinolines and analogous polycyclic derivativesGisela C. Muscia0Juan P. Carnevale1Ayelen Luczywo2María Victoria Peláez3Ailen Rodríguez Ó Toole4Graciela Y. Buldain5Juan J. Casal6Silvia E. Asís7Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, C1113AAD Junín 956, Ciudad Autónoma de Buenos Aires, ArgentinaUniversidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, C1113AAD Junín 956, Ciudad Autónoma de Buenos Aires, ArgentinaUniversidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, C1113AAD Junín 956, Ciudad Autónoma de Buenos Aires, ArgentinaUniversidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, C1113AAD Junín 956, Ciudad Autónoma de Buenos Aires, ArgentinaUniversidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, C1113AAD Junín 956, Ciudad Autónoma de Buenos Aires, ArgentinaUniversidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, C1113AAD Junín 956, Ciudad Autónoma de Buenos Aires, ArgentinaUniversidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, C1113AAD Junín 956, Ciudad Autónoma de Buenos Aires, Argentina; CONICET, Centro de Investigaciones en Bionanociencias, Polo Científico Tecnológico, C1425FQB Godoy Cruz 2390, Ciudad Autónoma de Buenos Aires, Argentina; Corresponding authors at: Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, Junín 956 C1113AAD, Ciudad Autónoma de Buenos Aires, Argentina.Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, C1113AAD Junín 956, Ciudad Autónoma de Buenos Aires, Argentina; Corresponding authors at: Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Departamento de Química Orgánica, Junín 956 C1113AAD, Ciudad Autónoma de Buenos Aires, Argentina.The multicomponent syntheses of 2,4-di-aryl-quinolines and analogous polycyclic derivatives as anti-tuberculosis agents were described. They were prepared via Beyer and Friedländer methods under microwave irradiation in short reaction times and good yields. Several homogeneous and heterogeneous acid catalysts were compared for preparing 2,4-di-arylquinolines and among them trifluoroacetic acid (TFA) reached the higher yields. Two derivatives exhibited activity against Mycobacterium tuberculosis H37Rv (Mtb), underwent additional testing and were considered lead compounds. The synthesis of a series of polycyclic analogous led to six new active compounds and a Quantitative Structure Activity Relationship study (QSAR) study was established. Keywords: Substituted quinolines, DARQ, Microwave-assisted synthesis, Catalysis, Mycobacterium tuberculosis, QSARhttp://www.sciencedirect.com/science/article/pii/S1878535218302053 |
| spellingShingle | Gisela C. Muscia Juan P. Carnevale Ayelen Luczywo María Victoria Peláez Ailen Rodríguez Ó Toole Graciela Y. Buldain Juan J. Casal Silvia E. Asís Synthesis, anti-tuberculosis activity and QSAR study of 2,4-diarylquinolines and analogous polycyclic derivatives Arabian Journal of Chemistry |
| title | Synthesis, anti-tuberculosis activity and QSAR study of 2,4-diarylquinolines and analogous polycyclic derivatives |
| title_full | Synthesis, anti-tuberculosis activity and QSAR study of 2,4-diarylquinolines and analogous polycyclic derivatives |
| title_fullStr | Synthesis, anti-tuberculosis activity and QSAR study of 2,4-diarylquinolines and analogous polycyclic derivatives |
| title_full_unstemmed | Synthesis, anti-tuberculosis activity and QSAR study of 2,4-diarylquinolines and analogous polycyclic derivatives |
| title_short | Synthesis, anti-tuberculosis activity and QSAR study of 2,4-diarylquinolines and analogous polycyclic derivatives |
| title_sort | synthesis anti tuberculosis activity and qsar study of 2 4 diarylquinolines and analogous polycyclic derivatives |
| url | http://www.sciencedirect.com/science/article/pii/S1878535218302053 |
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