A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules
The current role of the “Green Chemistry Protocol” in multicomponent reactions is first highlighted. Then, the green approach to the production of three novel hybrid diindolylmethanes-phenylboronic acids via a 3MCR is discussed, which features the following: solventless conditions, the use of microw...
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| Format: | Article |
| Language: | English |
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Wiley
2013-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2013/531208 |
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| author | Mónica Zarco Juarez Joel Omar Martínez Olivia Noguez Cordova María Inés Nicolás Vazquez Teresa Ramírez-Apan Javier Pérez Flores René Miranda Ruvalcaba Gabriel Arturo Arroyo Razo |
| author_facet | Mónica Zarco Juarez Joel Omar Martínez Olivia Noguez Cordova María Inés Nicolás Vazquez Teresa Ramírez-Apan Javier Pérez Flores René Miranda Ruvalcaba Gabriel Arturo Arroyo Razo |
| author_sort | Mónica Zarco Juarez |
| collection | DOAJ |
| description | The current role of the “Green Chemistry Protocol” in multicomponent reactions is first highlighted. Then, the green approach to the production of three novel hybrid diindolylmethanes-phenylboronic acids via a 3MCR is discussed, which features the following: solventless conditions, the use of microwave irradiation to activate the reactions, the absence of catalyst, and an efficient atom economy. The products were achieved with moderate yields (41–61%) within a short time frame (5 min) and appropriately characterized by elemental analysis and spectroscopic methods (NMR: 1H, 13C, 11B; MS: EI, CI, FAB+, HRMS). During the FAB+ MS determinations, various artifacts that are associated with the boron atom via an interaction with thioglycerol from the matrix were noted in the corresponding FAB+ mass spectra; in addition, the accurate mass determination of these adducts unequivocally confirmed the presence of the target molecules. Moreover, the activity of these target molecules was evaluated in the presence of six cancer cell lines (U251 = glia of the central nerve system, PC-3 = prostate, K562 = leukemia, HCT-15 = colon, MCF-7 = breast, and SKLU-1 = lung), which resulted in the meta-regioisomer being the most active. Finally, the products were also analyzed using computational chemistry in order to determine their most stable geometries and reactivities by computing the respective molecular electrostatic potentials. |
| format | Article |
| id | doaj-art-9e6fb228743d4d4bba41e54c23eda2e1 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2013-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-9e6fb228743d4d4bba41e54c23eda2e12025-02-03T07:26:18ZengWileyJournal of Chemistry2090-90632090-90712013-01-01201310.1155/2013/531208531208A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic MoleculesMónica Zarco Juarez0Joel Omar Martínez1Olivia Noguez Cordova2María Inés Nicolás Vazquez3Teresa Ramírez-Apan4Javier Pérez Flores5René Miranda Ruvalcaba6Gabriel Arturo Arroyo Razo7Departamento de Química, Facultad de Estudios Superiores Cuautitlán-Campus 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, 54740 México DF, MexicoDepartamento de Química, Facultad de Estudios Superiores Cuautitlán-Campus 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, 54740 México DF, MexicoDepartamento de Química, Facultad de Estudios Superiores Cuautitlán-Campus 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, 54740 México DF, MexicoDepartamento de Química, Facultad de Estudios Superiores Cuautitlán-Campus 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, 54740 México DF, MexicoInstituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán, 04510 México DF, MexicoInstituto de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Coyoacán, 04510 México DF, MexicoDepartamento de Química, Facultad de Estudios Superiores Cuautitlán-Campus 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, 54740 México DF, MexicoDepartamento de Química, Facultad de Estudios Superiores Cuautitlán-Campus 1, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, 54740 México DF, MexicoThe current role of the “Green Chemistry Protocol” in multicomponent reactions is first highlighted. Then, the green approach to the production of three novel hybrid diindolylmethanes-phenylboronic acids via a 3MCR is discussed, which features the following: solventless conditions, the use of microwave irradiation to activate the reactions, the absence of catalyst, and an efficient atom economy. The products were achieved with moderate yields (41–61%) within a short time frame (5 min) and appropriately characterized by elemental analysis and spectroscopic methods (NMR: 1H, 13C, 11B; MS: EI, CI, FAB+, HRMS). During the FAB+ MS determinations, various artifacts that are associated with the boron atom via an interaction with thioglycerol from the matrix were noted in the corresponding FAB+ mass spectra; in addition, the accurate mass determination of these adducts unequivocally confirmed the presence of the target molecules. Moreover, the activity of these target molecules was evaluated in the presence of six cancer cell lines (U251 = glia of the central nerve system, PC-3 = prostate, K562 = leukemia, HCT-15 = colon, MCF-7 = breast, and SKLU-1 = lung), which resulted in the meta-regioisomer being the most active. Finally, the products were also analyzed using computational chemistry in order to determine their most stable geometries and reactivities by computing the respective molecular electrostatic potentials.http://dx.doi.org/10.1155/2013/531208 |
| spellingShingle | Mónica Zarco Juarez Joel Omar Martínez Olivia Noguez Cordova María Inés Nicolás Vazquez Teresa Ramírez-Apan Javier Pérez Flores René Miranda Ruvalcaba Gabriel Arturo Arroyo Razo A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules Journal of Chemistry |
| title | A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules |
| title_full | A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules |
| title_fullStr | A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules |
| title_full_unstemmed | A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules |
| title_short | A Green Approach to the Production of Hybrid Diindolylmethane-Phenylboronic Acids via a 3MCR: Promising Antineoplasic Molecules |
| title_sort | green approach to the production of hybrid diindolylmethane phenylboronic acids via a 3mcr promising antineoplasic molecules |
| url | http://dx.doi.org/10.1155/2013/531208 |
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