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Mar. Drugs 2014, 12(2), 1116-1130; doi:10.3390/md12021116
Article

Tanjungides A and B: New Antitumoral Bromoindole Derived Compounds from Diazona cf formosa. Isolation and Total Synthesis

1
, 1
, 1
, 1
, 2
, 1
, 1
 and 1,*
1 Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain 2 Fundación MEDINA, Avda. del Conocimiento 3, Parque Tecnológico de Ciencias de la Salud, Granada 18016, Spain
* Author to whom correspondence should be addressed.
Received: 2 December 2013 / Revised: 16 December 2013 / Accepted: 24 January 2014 / Published: 21 February 2014
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Abstract

Tanjungides A (1) (Z isomer) and B (2) (E isomer), two novel dibrominated indole enamides, have been isolated from the tunicate Diazona cf formosa. Their structures were determined by spectroscopic methods including HRMS, and extensive 1D and 2D NMR. The stereochemistry of the cyclised cystine present in both compounds was determined by Marfey’s analysis after chemical degradation and hydrolysis. We also report the first total synthesis of these compounds using methyl 1H-indole-3-carboxylate as starting material and a linear sequence of 11 chemical steps. Tanjungides A and B exhibit significant cytotoxicity against human tumor cell lines.
Keywords: bromoindole; tunicate; Diazona cf formosa; cytotoxicity; isolation; structure elucidation; total synthesis bromoindole; tunicate; Diazona cf formosa; cytotoxicity; isolation; structure elucidation; total synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Murcia, C.; Coello, L.; Fernández, R.; Martín, M.J.; Reyes, F.; Francesch, A.; Munt, S.; Cuevas, C. Tanjungides A and B: New Antitumoral Bromoindole Derived Compounds from Diazona cf formosa. Isolation and Total Synthesis. Mar. Drugs 2014, 12, 1116-1130.

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