Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes
Schiff bases have been important compounds ever since their discovery and are both found in nature and synthesized in the laboratory. They participate in a variety of synthetic processes and possess desirable biological activity, including antibacterial, anti-inflammatory, antioxidant, and anticance...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-11-01
|
| Series: | Chemistry Proceedings |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2673-4583/12/1/43 |
| _version_ | 1797595535681519616 |
|---|---|
| author | Esteban Aguilar-Llanos Saskya E. Carrera-Pacheco Rebeca González-Pastor Johana Zúñiga-Miranda Cristina Rodríguez-Pólit Juan Carlos Romero-Benavides Jorge Heredia-Moya |
| author_facet | Esteban Aguilar-Llanos Saskya E. Carrera-Pacheco Rebeca González-Pastor Johana Zúñiga-Miranda Cristina Rodríguez-Pólit Juan Carlos Romero-Benavides Jorge Heredia-Moya |
| author_sort | Esteban Aguilar-Llanos |
| collection | DOAJ |
| description | Schiff bases have been important compounds ever since their discovery and are both found in nature and synthesized in the laboratory. They participate in a variety of synthetic processes and possess desirable biological activity, including antibacterial, anti-inflammatory, antioxidant, and anticancer activity, among others. In this study, eight Schiff bases derived from the reaction of 4-aminoantipyrine with various cinnamaldehydes have been synthesized and characterized. All derivatives were tested in vitro on several human carcinoma cell lines to determine their antitumor activity and against different bacteria strains of clinical and food industry importance to evaluate their antibacterial activity. Several of the Schiff bases evaluated inhibited tumor cell growth in a dose-dependent manner. The compound that exhibited the most activity against all cell lines had IC<sub>50</sub> values of less than 18 μM. On the other hand, during the evaluation of the antibacterial activity, only two Schiff base derivatives showed interesting antibacterial effects, with MIC values under 250 μM. These two Schiff base derivatives mainly exhibited a bacteriostatic effect against most of the studied bacterial strains. It is interesting to note that the same Schiff base presents the best activity in both biological evaluations. |
| first_indexed | 2024-03-11T02:37:58Z |
| format | Article |
| id | doaj.art-7b410ae5179448e893d1dccf3b5522e9 |
| institution | Directory Open Access Journal |
| issn | 2673-4583 |
| language | English |
| last_indexed | 2024-03-11T02:37:58Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry Proceedings |
| spelling | doaj.art-7b410ae5179448e893d1dccf3b5522e92023-11-18T09:48:12ZengMDPI AGChemistry Proceedings2673-45832022-11-011214310.3390/ecsoc-26-13684Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and CinnamaldehydesEsteban Aguilar-Llanos0Saskya E. Carrera-Pacheco1Rebeca González-Pastor2Johana Zúñiga-Miranda3Cristina Rodríguez-Pólit4Juan Carlos Romero-Benavides5Jorge Heredia-Moya6Facultad de Ciencias Químicas, Universidad Central del Ecuador, Francisco Viteri s/n y Gilberto Gato Sobral, Quito 170521, EcuadorCentro de Investigación Biomédica (CENBIO), Facultad de Ciencias de la Salud Eugenio Espejo, Universidad UTE, Quito 170527, EcuadorCentro de Investigación Biomédica (CENBIO), Facultad de Ciencias de la Salud Eugenio Espejo, Universidad UTE, Quito 170527, EcuadorCentro de Investigación Biomédica (CENBIO), Facultad de Ciencias de la Salud Eugenio Espejo, Universidad UTE, Quito 170527, EcuadorCentro de Investigación Biomédica (CENBIO), Facultad de Ciencias de la Salud Eugenio Espejo, Universidad UTE, Quito 170527, EcuadorDepartamento de Química, Facultad de Ciencias Exactas y Naturales, Universidad Técnica Particular de Loja, Loja 1101608, EcuadorCentro de Investigación Biomédica (CENBIO), Facultad de Ciencias de la Salud Eugenio Espejo, Universidad UTE, Quito 170527, EcuadorSchiff bases have been important compounds ever since their discovery and are both found in nature and synthesized in the laboratory. They participate in a variety of synthetic processes and possess desirable biological activity, including antibacterial, anti-inflammatory, antioxidant, and anticancer activity, among others. In this study, eight Schiff bases derived from the reaction of 4-aminoantipyrine with various cinnamaldehydes have been synthesized and characterized. All derivatives were tested in vitro on several human carcinoma cell lines to determine their antitumor activity and against different bacteria strains of clinical and food industry importance to evaluate their antibacterial activity. Several of the Schiff bases evaluated inhibited tumor cell growth in a dose-dependent manner. The compound that exhibited the most activity against all cell lines had IC<sub>50</sub> values of less than 18 μM. On the other hand, during the evaluation of the antibacterial activity, only two Schiff base derivatives showed interesting antibacterial effects, with MIC values under 250 μM. These two Schiff base derivatives mainly exhibited a bacteriostatic effect against most of the studied bacterial strains. It is interesting to note that the same Schiff base presents the best activity in both biological evaluations.https://www.mdpi.com/2673-4583/12/1/43Schiff base4-aminoantypirinecinnamaldehydesantibacterialanticancer |
| spellingShingle | Esteban Aguilar-Llanos Saskya E. Carrera-Pacheco Rebeca González-Pastor Johana Zúñiga-Miranda Cristina Rodríguez-Pólit Juan Carlos Romero-Benavides Jorge Heredia-Moya Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes Chemistry Proceedings Schiff base 4-aminoantypirine cinnamaldehydes antibacterial anticancer |
| title | Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes |
| title_full | Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes |
| title_fullStr | Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes |
| title_full_unstemmed | Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes |
| title_short | Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes |
| title_sort | synthesis and evaluation of biological activities of schiff base derivatives of 4 aminoantipyrine and cinnamaldehydes |
| topic | Schiff base 4-aminoantypirine cinnamaldehydes antibacterial anticancer |
| url | https://www.mdpi.com/2673-4583/12/1/43 |
| work_keys_str_mv | AT estebanaguilarllanos synthesisandevaluationofbiologicalactivitiesofschiffbasederivativesof4aminoantipyrineandcinnamaldehydes AT saskyaecarrerapacheco synthesisandevaluationofbiologicalactivitiesofschiffbasederivativesof4aminoantipyrineandcinnamaldehydes AT rebecagonzalezpastor synthesisandevaluationofbiologicalactivitiesofschiffbasederivativesof4aminoantipyrineandcinnamaldehydes AT johanazunigamiranda synthesisandevaluationofbiologicalactivitiesofschiffbasederivativesof4aminoantipyrineandcinnamaldehydes AT cristinarodriguezpolit synthesisandevaluationofbiologicalactivitiesofschiffbasederivativesof4aminoantipyrineandcinnamaldehydes AT juancarlosromerobenavides synthesisandevaluationofbiologicalactivitiesofschiffbasederivativesof4aminoantipyrineandcinnamaldehydes AT jorgeherediamoya synthesisandevaluationofbiologicalactivitiesofschiffbasederivativesof4aminoantipyrineandcinnamaldehydes |