title: Tanjungides A and B: new antitumoral bromoindole derived compounds from Diazona cf formosa. isolation and total synthesis.
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.
authors.affiliation: Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain. cmurcia@pharmamar.com.
authors.forename: Carmen
authors.initials: C
authors.lastname: Murcia
authors.affiliation: Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain. lcoello@pharmamar.com.
authors.forename: Laura
authors.initials: L
authors.lastname: Coello
authors.affiliation: Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain. rfernandez@pharmamar.com.
authors.forename: Rogelio
authors.initials: R
authors.lastname: Fernández
authors.affiliation: Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain. mjmartin@pharmamar.com.
authors.forename: María Jesús
authors.initials: MJ
authors.lastname: Martín
authors.affiliation: Fundación MEDINA, Avda. del Conocimiento 3, Parque Tecnológico de Ciencias de la Salud, Granada 18016, Spain. fernando.reyes@medinaandalucia.es.
authors.forename: Fernando
authors.initials: F
authors.lastname: Reyes
authors.affiliation: Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain. afrancesch@pharmamar.com.
authors.forename: Andrés
authors.initials: A
authors.lastname: Francesch
authors.affiliation: Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain. smunt@pharmamar.com.
authors.forename: Simon
authors.initials: S
authors.lastname: Munt
authors.affiliation: Medicinal Chemistry Department, PharmaMar S.A., Avda. de los Reyes 1, Pol. In. La Mina, Colmenar Viejo, Madrid 28770, Spain. ccuevas@pharmamar.com.
authors.forename: Carmen
authors.initials: C
authors.lastname: Cuevas
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D006801:Humans; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D009369:Neoplasms / Q000188:drug therapy* / Q000453:epidemiology; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014561:Urochordata / Q000378:metabolism*
chemical_list: D000970:Antineoplastic Agents; D007211:Indoles; D010456:Peptides, Cyclic; C000591704:tanjungide A; C000591705:tanjungide B