Tanjungides A and B: New Antitumoral Bromoindole Derived Compounds from Diazona cf formosa. Isolation and Total Synthesis |
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| Authors: | Carmen Murcia Laura Coello Rogelio Fernández María Jesús Martín Fernando Reyes Andrés Francesch Simon Munt Carmen Cuevas |
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| Affiliation: | 1.Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain; E-Mails: (C.M.); (L.C.); (R.F.); (M.J.M.); (A.F.); (S.M.);2.Fundación MEDINA, Avda. del Conocimiento 3, Parque Tecnológico de Ciencias de la Salud, Granada 18016, Spain; E-Mail: |
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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. |
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| Keywords: | bromoindole tunicate Diazona cf formosa cytotoxicity isolation structure elucidation total synthesis |
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