Molecules 2012, 17(6), 7042-7056; doi:10.3390/molecules17067042
Article

Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones

1 Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 6094411, 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: 18 April 2012; in revised form: 23 May 2012 / Accepted: 25 May 2012 / Published: 7 June 2012
(This article belongs to the Section Organic Synthesis)
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Abstract: The synthesis of 4-methoxycarbonyl-3-methylisoquinolinequinone (1) and a variety of its substitution products with amino-, alkylamino and halogen groups on the quinone nucleus is reported. The series of 6-, 7- and 6,7-subtituted isoquinolinequinones were evaluated in vitro for their cytotoxic activity using the MTT colorimetric method. All the newly synthesized compounds showed moderate to high potency against MRC-5 healthy lung fibroblasts and four human tumor cell lines: AGS gastric adenocarcinoma, SK-MES-1 lung, J82 bladder carcinoma, and HL-60 leukemia cells. Among the series, compounds 4b, 12 and 13 exhibited interesting antitumor activity against human gastric adenocarcinoma, human lung and human bladder carcinoma cancer cells. 7-Amino-6-bromoisoquinoline-5,8-quinone (13) was found to be the most promising active compound against the tested cancer cell lines, with IC50 values in the 0.21−0.49 mM range, lower than the anti-cancer agent etoposide used as reference.
Keywords: aminoisoquinoline-5,8-quinones; regioselectivity; anticancer; SAR analysis

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MDPI and ACS Style

Delgado, V.; Ibacache, A.; Theoduloz, C.; Valderrama, J.A. Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones. Molecules 2012, 17, 7042-7056.

AMA Style

Delgado V, Ibacache A, Theoduloz C, Valderrama JA. Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones. Molecules. 2012; 17(6):7042-7056.

Chicago/Turabian Style

Delgado, Virginia; Ibacache, Andrea; Theoduloz, Cristina; Valderrama, Jaime A. 2012. "Synthesis and in Vitro Cytotoxic Evaluation of Aminoquinones Structurally Related to Marine Isoquinolinequinones." Molecules 17, no. 6: 7042-7056.

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