2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline
A 2,4-diarylquinoline derivative, 2-(4-chlorophenyl)-4-(3,4-dimethoxyphenyl)-6-methoxy-3-methylquinoline, was synthesized in a conventional two-step procedure from <i>p</i>-anisidine, <i>p</i>-chlorobenzaldehyde and methyl isoeugenol as available starting reagents through a s...
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MDPI AG
2022-06-01
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| Online Access: | https://www.mdpi.com/1422-8599/2022/2/M1383 |
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| author | Duván A. Rodríguez Enciso Carlos E. Puerto Galvis Vladimir V. Kouznetsov |
| author_facet | Duván A. Rodríguez Enciso Carlos E. Puerto Galvis Vladimir V. Kouznetsov |
| author_sort | Duván A. Rodríguez Enciso |
| collection | DOAJ |
| description | A 2,4-diarylquinoline derivative, 2-(4-chlorophenyl)-4-(3,4-dimethoxyphenyl)-6-methoxy-3-methylquinoline, was synthesized in a conventional two-step procedure from <i>p</i>-anisidine, <i>p</i>-chlorobenzaldehyde and methyl isoeugenol as available starting reagents through a sequence of BF<sub>3</sub>·OEt<sub>2</sub>-catalyzed Povarov cycloaddition reaction/oxidative dehydrogenation aromatization processes under microwave irradiation conditions in the presence of a green oxidative I<sub>2</sub>-DMSO system. The structure of the compound was fully characterized by FT-IR, <sup>1</sup>H and <sup>13</sup>C-NMR, ESI-MS, and elemental analysis. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the Molinspiration Cheminformatics software. The diarylquinoline molecule obtained is an interesting model with increased lipophilicity and thus permeability, an important descriptor for quinoline-based drug design. Such types of derivatives are known for their anticancer, antitubercular, antifungal, and antiviral activities. |
| first_indexed | 2024-03-09T22:56:48Z |
| format | Article |
| id | doaj.art-18a5e292e87649d0b41e6d5bad2662dd |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T22:56:48Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-18a5e292e87649d0b41e6d5bad2662dd2023-11-23T18:08:38ZengMDPI AGMolbank1422-85992022-06-0120222M138310.3390/M13832-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinolineDuván A. Rodríguez Enciso0Carlos E. Puerto Galvis1Vladimir V. Kouznetsov2Laboratorio de Química Orgánica y Biomolecular, CMN, Parque Tecnológico Guatiguará, Km 2 vía Refugio, Universidad Industrial de Santander, Piedecuesta A.A. 681011, ColombiaLaboratorio de Química Orgánica y Biomolecular, CMN, Parque Tecnológico Guatiguará, Km 2 vía Refugio, Universidad Industrial de Santander, Piedecuesta A.A. 681011, ColombiaLaboratorio de Química Orgánica y Biomolecular, CMN, Parque Tecnológico Guatiguará, Km 2 vía Refugio, Universidad Industrial de Santander, Piedecuesta A.A. 681011, ColombiaA 2,4-diarylquinoline derivative, 2-(4-chlorophenyl)-4-(3,4-dimethoxyphenyl)-6-methoxy-3-methylquinoline, was synthesized in a conventional two-step procedure from <i>p</i>-anisidine, <i>p</i>-chlorobenzaldehyde and methyl isoeugenol as available starting reagents through a sequence of BF<sub>3</sub>·OEt<sub>2</sub>-catalyzed Povarov cycloaddition reaction/oxidative dehydrogenation aromatization processes under microwave irradiation conditions in the presence of a green oxidative I<sub>2</sub>-DMSO system. The structure of the compound was fully characterized by FT-IR, <sup>1</sup>H and <sup>13</sup>C-NMR, ESI-MS, and elemental analysis. Its physicochemical parameters (Lipinski’s descriptors) were also calculated using the Molinspiration Cheminformatics software. The diarylquinoline molecule obtained is an interesting model with increased lipophilicity and thus permeability, an important descriptor for quinoline-based drug design. Such types of derivatives are known for their anticancer, antitubercular, antifungal, and antiviral activities.https://www.mdpi.com/1422-8599/2022/2/M13832,4-diarylquinolinemethyl isoeugenolPovarov reactionoxidative dehydrogenation aromatization processLipinski’s descriptors |
| spellingShingle | Duván A. Rodríguez Enciso Carlos E. Puerto Galvis Vladimir V. Kouznetsov 2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline Molbank 2,4-diarylquinoline methyl isoeugenol Povarov reaction oxidative dehydrogenation aromatization process Lipinski’s descriptors |
| title | 2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline |
| title_full | 2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline |
| title_fullStr | 2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline |
| title_full_unstemmed | 2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline |
| title_short | 2-(4-Chlorophenyl)-4-(3,4-dimethoxy-phenyl)-6-methoxy-3-methylquinoline |
| title_sort | 2 4 chlorophenyl 4 3 4 dimethoxy phenyl 6 methoxy 3 methylquinoline |
| topic | 2,4-diarylquinoline methyl isoeugenol Povarov reaction oxidative dehydrogenation aromatization process Lipinski’s descriptors |
| url | https://www.mdpi.com/1422-8599/2022/2/M1383 |
| work_keys_str_mv | AT duvanarodriguezenciso 24chlorophenyl434dimethoxyphenyl6methoxy3methylquinoline AT carlosepuertogalvis 24chlorophenyl434dimethoxyphenyl6methoxy3methylquinoline AT vladimirvkouznetsov 24chlorophenyl434dimethoxyphenyl6methoxy3methylquinoline |