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• Delgado, V
• Ibacache, A
• Arancibia, V
• Theoduloz, C
• Valderrama, JA.
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• Delgado, V
• Ibacache, A
• Arancibia, V
• Theoduloz, C
• Valderrama, JA.
• [+] on PubMed
• Delgado, V
• Ibacache, A
• Arancibia, V
• Theoduloz, C
• Valderrama, JA.

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Molecules 2013, 18(1), 721-734; doi:10.3390/molecules18010721

Article

Synthesis and in Vitro Antiproliferative Activity of New Phenylaminoisoquinolinequinones against Cancer Cell Lines

Virginia Delgado ¹ , Andrea Ibacache ¹ , Verónica Arancibia ¹ , Cristina Theoduloz ²  and Jaime A. Valderrama ^1,3,*

¹ Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 26094411, Chile ² Facultad de Ciencias de la Salud, Universidad de Talca, Talca 3460000, Chile ³ Instituto de Etno-Farmacología (IDE), Universidad Arturo Prat, Casilla 121, Iquique 1100000, Chile

* Author to whom correspondence should be addressed.

Received: 10 December 2012; in revised form: 27 December 2012 / Accepted: 31 December 2012 / Published: 8 January 2013

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Abstract: A variety of phenylaminoisoquinolinequinones were synthesized and tested for their antiproliferative activity against three human-tumor derived cancer cell lines. The new aminoquinones were prepared from 4-methoxycarbonyl-3-methylisoquinoline-5,8-quinone (1) via acid-induced amination and bromination reactions. Remarkable differences in antiproliferative activity were observed depending upon the location and donor capacity of the substituted phenylamino group at the quinone nucleus. The effect of the substituents on the biological activity is discussed in terms of the donor-acceptor interactions which were evaluated through the redox properties of the aminoquinones.

Keywords: phenylaminoisoquinoline-5,8-quinones; regioselectivity; half-wave potential; antiproliferative activity; SAR analysis

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