Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [<i>d</i>] [1,3] Azoles
A series of benzo [<i>d</i>] [1,3] azoles 2-substituted with benzyl- and allyl-sulfanyl groups were synthesized, and their cytotoxic activities were in vitro evaluated against a panel of six human cancer cell lines. The results showed that compounds BTA-1 and BMZ-2 have the best inhibito...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/9/2780 |
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| author | Ozvaldo Linares-Anaya Alcives Avila-Sorrosa Francisco Díaz-Cedillo Luis Ángel Gil-Ruiz José Correa-Basurto Domingo Salazar-Mendoza Adrian L. Orjuela Jorge Alí-Torres María Teresa Ramírez-Apan David Morales-Morales |
| author_facet | Ozvaldo Linares-Anaya Alcives Avila-Sorrosa Francisco Díaz-Cedillo Luis Ángel Gil-Ruiz José Correa-Basurto Domingo Salazar-Mendoza Adrian L. Orjuela Jorge Alí-Torres María Teresa Ramírez-Apan David Morales-Morales |
| author_sort | Ozvaldo Linares-Anaya |
| collection | DOAJ |
| description | A series of benzo [<i>d</i>] [1,3] azoles 2-substituted with benzyl- and allyl-sulfanyl groups were synthesized, and their cytotoxic activities were in vitro evaluated against a panel of six human cancer cell lines. The results showed that compounds BTA-1 and BMZ-2 have the best inhibitory effects, compound BMZ-2 being comparable in some cases with the reference drug tamoxifen and exhibiting a low cytotoxic effect against healthy cells. In silico molecular coupling studies at the tamoxifen binding site of ERα and GPER receptors revealed affinity and the possible mode of interaction of both compounds BTA-1 and BMZ-2. |
| first_indexed | 2024-03-10T11:36:36Z |
| format | Article |
| id | doaj.art-73234c2bf41b4dd293958578f09434e9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T11:36:36Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-73234c2bf41b4dd293958578f09434e92023-11-21T18:49:24ZengMDPI AGMolecules1420-30492021-05-01269278010.3390/molecules26092780Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [<i>d</i>] [1,3] AzolesOzvaldo Linares-Anaya0Alcives Avila-Sorrosa1Francisco Díaz-Cedillo2Luis Ángel Gil-Ruiz3José Correa-Basurto4Domingo Salazar-Mendoza5Adrian L. Orjuela6Jorge Alí-Torres7María Teresa Ramírez-Apan8David Morales-Morales9Instituto Politécnico Nacional, Departamento de Química Orgánica, Carpio y Plan de Ayala S/N, Escuela Nacional de Ciencias Biológicas, Colonia Santo Tomás, Ciudad de México 11340, MexicoInstituto Politécnico Nacional, Departamento de Química Orgánica, Carpio y Plan de Ayala S/N, Escuela Nacional de Ciencias Biológicas, Colonia Santo Tomás, Ciudad de México 11340, MexicoInstituto Politécnico Nacional, Departamento de Química Orgánica, Carpio y Plan de Ayala S/N, Escuela Nacional de Ciencias Biológicas, Colonia Santo Tomás, Ciudad de México 11340, MexicoInstituto Politécnico Nacional, Departamento de Química Orgánica, Carpio y Plan de Ayala S/N, Escuela Nacional de Ciencias Biológicas, Colonia Santo Tomás, Ciudad de México 11340, MexicoLaboratorio de Diseño y Desarrollo de Nuevos Fármacos e Innovación Biotecnológica, Instituto Politécnico Nacional, Escuela Superior de Medicina, Ciudad de México 11340, MexicoCarretera a Acatlima, Huajuapan de León, Universidad Tecnológica de la Mixteca, Oaxaca 69000, MexicoDepartamento de Química, Universidad Nacional de Colombia-Sede, Bogotá 111321, ColombiaDepartamento de Química, Universidad Nacional de Colombia-Sede, Bogotá 111321, ColombiaInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Ciudad de México 04510, MexicoInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Ciudad de México 04510, MexicoA series of benzo [<i>d</i>] [1,3] azoles 2-substituted with benzyl- and allyl-sulfanyl groups were synthesized, and their cytotoxic activities were in vitro evaluated against a panel of six human cancer cell lines. The results showed that compounds BTA-1 and BMZ-2 have the best inhibitory effects, compound BMZ-2 being comparable in some cases with the reference drug tamoxifen and exhibiting a low cytotoxic effect against healthy cells. In silico molecular coupling studies at the tamoxifen binding site of ERα and GPER receptors revealed affinity and the possible mode of interaction of both compounds BTA-1 and BMZ-2.https://www.mdpi.com/1420-3049/26/9/27802-substituted benzo [<i>d</i>] [1,3] azolesin vitro cytotoxicitybreast cancerERα and GPERmolecular docking |
| spellingShingle | Ozvaldo Linares-Anaya Alcives Avila-Sorrosa Francisco Díaz-Cedillo Luis Ángel Gil-Ruiz José Correa-Basurto Domingo Salazar-Mendoza Adrian L. Orjuela Jorge Alí-Torres María Teresa Ramírez-Apan David Morales-Morales Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [<i>d</i>] [1,3] Azoles Molecules 2-substituted benzo [<i>d</i>] [1,3] azoles in vitro cytotoxicity breast cancer ERα and GPER molecular docking |
| title | Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [<i>d</i>] [1,3] Azoles |
| title_full | Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [<i>d</i>] [1,3] Azoles |
| title_fullStr | Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [<i>d</i>] [1,3] Azoles |
| title_full_unstemmed | Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [<i>d</i>] [1,3] Azoles |
| title_short | Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [<i>d</i>] [1,3] Azoles |
| title_sort | synthesis characterization and preliminary in vitro cytotoxic evaluation of a series of 2 substituted benzo i d i 1 3 azoles |
| topic | 2-substituted benzo [<i>d</i>] [1,3] azoles in vitro cytotoxicity breast cancer ERα and GPER molecular docking |
| url | https://www.mdpi.com/1420-3049/26/9/2780 |
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