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Article

Synthesis, Cytotoxic Activity and In Silico Study of Novel Dihydropyridine Carboxylic Acids Derivatives

by
Ricardo Ballinas-Indilí
1,
María Inés Nicolás-Vázquez
1,
Joel Martínez
1,
María Teresa Ramírez-Apan
2,
Cecilio Álvarez-Toledano
2,
Alfredo Toscano
2,
Maricarmen Hernández-Rodríguez
3,
Elvia Mera Jiménez
3 and
René Miranda Ruvalcaba
1,*
1
Departamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán Campo 1, Universidad Nacional Autónoma de México, Avenida 1o de Mayo s/n, Colonia Santa María las Torres, Cuautitlán Izcalli 54740, Mexico
2
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, Mexico City 04510, Mexico
3
Laboratorio de Cultivo Celular, Sección de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, Mexico City 11340, Mexico
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2023, 24(20), 15414; https://doi.org/10.3390/ijms242015414
Submission received: 8 September 2023 / Revised: 11 October 2023 / Accepted: 18 October 2023 / Published: 21 October 2023
(This article belongs to the Section Physical Chemistry and Chemical Physics)
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Abstract

To aid the possible prevention of multidrug resistance in tumors and cause lower toxicity, a set of sixteen novel dihydropyridine carboxylic acids derivatives 3a–p were produced; thus, the activation of various ynones with triflic anhydride was performed, involving a nucleophilic addition of several bis(trimethylsilyl) ketene acetals, achieving good yields requiring easy workup. The target molecules were unequivocally characterized by common spectroscopic methods. In addition, two of the tested compounds (3a, and 3b) were selected to perform in silico studies due to the highest cytotoxic activity towards the HCT-15 cell line (7.94 ± 1.6 μM and 9.24 ± 0.9 μM, respectively). Employing theoretical calculations with density functional theory (DFT) using the B3LYP/6-311++G(d,p) showed that the molecular parameters correlate adequately with the experimental results. In contrast, predictions employing Osiris Property Explorer showed that compounds 3a and 3b present physicochemical characteristics that would likely make it an orally active drug. Moreover, the performance of Docking studies with proteins related to the apoptosis pathway allowed a proposal of which compounds could interact with PARP-1 protein. Pondering the obtained results (synthesis, in silico, and cytotoxic activity) of the target compounds, they can be judged as suitable antineoplastic agent candidates.
Keywords: ynones; dihydropyridine carboxylic acid; cytotoxic activity; in silico DFT ynones; dihydropyridine carboxylic acid; cytotoxic activity; in silico DFT

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MDPI and ACS Style

Ballinas-Indilí, R.; Nicolás-Vázquez, M.I.; Martínez, J.; Ramírez-Apan, M.T.; Álvarez-Toledano, C.; Toscano, A.; Hernández-Rodríguez, M.; Mera Jiménez, E.; Miranda Ruvalcaba, R. Synthesis, Cytotoxic Activity and In Silico Study of Novel Dihydropyridine Carboxylic Acids Derivatives. Int. J. Mol. Sci. 2023, 24, 15414. https://doi.org/10.3390/ijms242015414

AMA Style

Ballinas-Indilí R, Nicolás-Vázquez MI, Martínez J, Ramírez-Apan MT, Álvarez-Toledano C, Toscano A, Hernández-Rodríguez M, Mera Jiménez E, Miranda Ruvalcaba R. Synthesis, Cytotoxic Activity and In Silico Study of Novel Dihydropyridine Carboxylic Acids Derivatives. International Journal of Molecular Sciences. 2023; 24(20):15414. https://doi.org/10.3390/ijms242015414

Chicago/Turabian Style

Ballinas-Indilí, Ricardo, María Inés Nicolás-Vázquez, Joel Martínez, María Teresa Ramírez-Apan, Cecilio Álvarez-Toledano, Alfredo Toscano, Maricarmen Hernández-Rodríguez, Elvia Mera Jiménez, and René Miranda Ruvalcaba. 2023. "Synthesis, Cytotoxic Activity and In Silico Study of Novel Dihydropyridine Carboxylic Acids Derivatives" International Journal of Molecular Sciences 24, no. 20: 15414. https://doi.org/10.3390/ijms242015414

APA Style

Ballinas-Indilí, R., Nicolás-Vázquez, M. I., Martínez, J., Ramírez-Apan, M. T., Álvarez-Toledano, C., Toscano, A., Hernández-Rodríguez, M., Mera Jiménez, E., & Miranda Ruvalcaba, R. (2023). Synthesis, Cytotoxic Activity and In Silico Study of Novel Dihydropyridine Carboxylic Acids Derivatives. International Journal of Molecular Sciences, 24(20), 15414. https://doi.org/10.3390/ijms242015414

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