Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates
Tuberculosis (TB) has been described as a global health crisis since the second half of the 1990s. <i>Mycobacterium tuberculosis</i> (Mtb), the etiologic agent of TB in humans, is a very successful pathogen, being the main cause of death in the population among infectious agents. In 2019...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/5/1215 |
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| author | Ana Flávia Borsoi Josiane Delgado Paz Kenia Pissinate Raoní Scheibler Rambo Víctor Zajaczkowski Pestana Cristiano Valim Bizarro Luiz Augusto Basso Pablo Machado |
| author_facet | Ana Flávia Borsoi Josiane Delgado Paz Kenia Pissinate Raoní Scheibler Rambo Víctor Zajaczkowski Pestana Cristiano Valim Bizarro Luiz Augusto Basso Pablo Machado |
| author_sort | Ana Flávia Borsoi |
| collection | DOAJ |
| description | Tuberculosis (TB) has been described as a global health crisis since the second half of the 1990s. <i>Mycobacterium tuberculosis</i> (Mtb), the etiologic agent of TB in humans, is a very successful pathogen, being the main cause of death in the population among infectious agents. In 2019, it was estimated that around 10 million individuals were contaminated by this bacillus and about 1.2 million succumbed to the disease. In recent years, our research group has reported the design and synthesis of quinoline derivatives as drug candidates for the treatment of TB. These compounds have demonstrated potent and selective growth inhibition of drug-susceptible and drug-resistant Mtb strains. Herein, a new synthetic approach was established providing efficient and rapid access (15 min) to a series of 4-alkoxy-6-methoxy-2-methylquinolines using ultrasound energy. The new synthetic protocol provides a simple procedure utilizing an open vessel system that affords the target products at satisfactory yields (45–84%) and elevated purities (≥95%). The methodology allows the evaluation of a larger number of molecules in assays against the bacillus, facilitating the determination of the structure–activity relationship with a reduced environmental cost. |
| first_indexed | 2024-03-09T00:33:53Z |
| format | Article |
| id | doaj.art-c035c06d4887429eb7100e70fcad1573 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T00:33:53Z |
| publishDate | 2021-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c035c06d4887429eb7100e70fcad15732023-12-11T18:18:15ZengMDPI AGMolecules1420-30492021-02-01265121510.3390/molecules26051215Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug CandidatesAna Flávia Borsoi0Josiane Delgado Paz1Kenia Pissinate2Raoní Scheibler Rambo3Víctor Zajaczkowski Pestana4Cristiano Valim Bizarro5Luiz Augusto Basso6Pablo Machado7Centro de Pesquisas em Biologia Molecular e Funcional, Instituto Nacional de Ciência e Tecnologia em Tuberculose, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900 Porto Alegre, Rio Grande do Sul, BrazilCentro de Pesquisas em Biologia Molecular e Funcional, Instituto Nacional de Ciência e Tecnologia em Tuberculose, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900 Porto Alegre, Rio Grande do Sul, BrazilCentro de Pesquisas em Biologia Molecular e Funcional, Instituto Nacional de Ciência e Tecnologia em Tuberculose, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900 Porto Alegre, Rio Grande do Sul, BrazilCentro de Pesquisas em Biologia Molecular e Funcional, Instituto Nacional de Ciência e Tecnologia em Tuberculose, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900 Porto Alegre, Rio Grande do Sul, BrazilCentro de Pesquisas em Biologia Molecular e Funcional, Instituto Nacional de Ciência e Tecnologia em Tuberculose, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900 Porto Alegre, Rio Grande do Sul, BrazilCentro de Pesquisas em Biologia Molecular e Funcional, Instituto Nacional de Ciência e Tecnologia em Tuberculose, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900 Porto Alegre, Rio Grande do Sul, BrazilCentro de Pesquisas em Biologia Molecular e Funcional, Instituto Nacional de Ciência e Tecnologia em Tuberculose, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900 Porto Alegre, Rio Grande do Sul, BrazilCentro de Pesquisas em Biologia Molecular e Funcional, Instituto Nacional de Ciência e Tecnologia em Tuberculose, Pontifícia Universidade Católica do Rio Grande do Sul, 90616-900 Porto Alegre, Rio Grande do Sul, BrazilTuberculosis (TB) has been described as a global health crisis since the second half of the 1990s. <i>Mycobacterium tuberculosis</i> (Mtb), the etiologic agent of TB in humans, is a very successful pathogen, being the main cause of death in the population among infectious agents. In 2019, it was estimated that around 10 million individuals were contaminated by this bacillus and about 1.2 million succumbed to the disease. In recent years, our research group has reported the design and synthesis of quinoline derivatives as drug candidates for the treatment of TB. These compounds have demonstrated potent and selective growth inhibition of drug-susceptible and drug-resistant Mtb strains. Herein, a new synthetic approach was established providing efficient and rapid access (15 min) to a series of 4-alkoxy-6-methoxy-2-methylquinolines using ultrasound energy. The new synthetic protocol provides a simple procedure utilizing an open vessel system that affords the target products at satisfactory yields (45–84%) and elevated purities (≥95%). The methodology allows the evaluation of a larger number of molecules in assays against the bacillus, facilitating the determination of the structure–activity relationship with a reduced environmental cost.https://www.mdpi.com/1420-3049/26/5/1215sonochemistryheterocyclic synthesisnew methodsantituberculosis drug discovery |
| spellingShingle | Ana Flávia Borsoi Josiane Delgado Paz Kenia Pissinate Raoní Scheibler Rambo Víctor Zajaczkowski Pestana Cristiano Valim Bizarro Luiz Augusto Basso Pablo Machado Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates Molecules sonochemistry heterocyclic synthesis new methods antituberculosis drug discovery |
| title | Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates |
| title_full | Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates |
| title_fullStr | Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates |
| title_full_unstemmed | Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates |
| title_short | Ultrasound-Assisted Synthesis of 4-Alkoxy-2-methylquinolines: An Efficient Method toward Antitubercular Drug Candidates |
| title_sort | ultrasound assisted synthesis of 4 alkoxy 2 methylquinolines an efficient method toward antitubercular drug candidates |
| topic | sonochemistry heterocyclic synthesis new methods antituberculosis drug discovery |
| url | https://www.mdpi.com/1420-3049/26/5/1215 |
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