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Molecules 2017, 22(12), 2281; https://doi.org/10.3390/molecules22122281

Access to New Cytotoxic Quinone-Amino Acid Conjugates Linked through A Vinylic Spacer from 2-Acylnaphthoquinones and Methyl 3-Aminocrotonate

1
Instituto de Ciencias Exactas y Naturales (ICEN), Universidad Arturo Prat Casilla 121, Iquique 1100000, Chile
2
Química y Farmacia, Facultad de Ciencias de la Salud, Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile
3
Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 6094411, Chile
4
Facultad de Ciencias de la Salud, Universidad de Talca, Talca 3460000, Chile
*
Authors to whom correspondence should be addressed.
Received: 28 November 2017 / Revised: 16 December 2017 / Accepted: 19 December 2017 / Published: 20 December 2017
(This article belongs to the Section Organic Chemistry)
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Abstract

The reaction of 2-acetyl- and 2-benzoyl-1,4-naphthoquinone with (Z)-methyl 3-(hydroxymethyl)aminocrotonate proceeds through a formal [3+3] process to yield the corresponding 1,2-dihydrobenzisoquinolinequinones in 63% and 72% yield, respectively. The reactions of 2-acyl-1,4-naphthoquinone with enaminones, derived from diverse l- and d-amino acid methyl esters, produced the corresponding naphthoquinone amino acids conjugates bonded through a vinyl spacer in the yields range 40–71%. The presence of not-separable isomers of the naphthoquinone amino acids conjugates in the 1H- and 13C-NMR spectra is explained by the existence of conformational isomers generated by hindered rotation of the substituent bonded to the quinone double bond. These new naphthoquinone amino acids conjugates were screened in vitro on normal and cancer cell lines and showed moderate cytotoxic activities. View Full-Text
Keywords: 2-acylnaphthoquinones; α-amino acid methyl esters; enaminones; quinone amino acid conjugates; cytotoxic activities 2-acylnaphthoquinones; α-amino acid methyl esters; enaminones; quinone amino acid conjugates; cytotoxic activities
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Valderrama, J.A.; Garrido, J.; Delgado, V.; Benites, J.; Theoduloz, C. Access to New Cytotoxic Quinone-Amino Acid Conjugates Linked through A Vinylic Spacer from 2-Acylnaphthoquinones and Methyl 3-Aminocrotonate. Molecules 2017, 22, 2281.

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