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Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues

Department of Organic Chemistry and Laboratory of Biologically Active Compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, Russia
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, 159 Prospekt 100 Let Vladivostoku, Vladivostok 690022, Russia
Federal Scientific Center of the East Asia Terrestrial Biodiversity (Institute of Biology and Soil Science), Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Let Vladivostoku, Vladivostok 690022, Russia
Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, Germany
Martini-Klinik Prostate Cancer Center, University Hospital Hamburg-Eppendorf, 20246 Hamburg, Germany
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(9), 496;
Received: 13 July 2019 / Revised: 21 August 2019 / Accepted: 22 August 2019 / Published: 25 August 2019
(This article belongs to the Special Issue Advances in Marine Alkaloids)
A simple approach toward the synthesis of the marine sponge derived pigment fascaplysin was used to obtain the marine alkaloids 3-bromofascaplysin and 3,10-dibromofascaplysin. These compounds were used for first syntheses of the alkaloids 14-bromoreticulatate and 14-bromoreticulatine. Preliminary bioassays showed that 14-bromoreticulatine has a selective antibiotic (to Pseudomonas aeruginosa) activity and reveals cytotoxicity toward human melanoma, colon, and prostate cancer cells. 3,10-Dibromofascaplysin was able to target metabolic activity of the prostate cancer cells, without disrupting cell membrane’s integrity and had a wide therapeutic window amongst the fascaplysin alkaloids. View Full-Text
Keywords: total synthesis; 14-bromoreticulatine; 3,10-dibromofascaplysin; bioactivity total synthesis; 14-bromoreticulatine; 3,10-dibromofascaplysin; bioactivity
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Zhidkov, M.E.; Smirnova, P.A.; Tryapkin, O.A.; Kantemirov, A.V.; Khudyakova, Y.V.; Malyarenko, O.S.; Ermakova, S.P.; Grigorchuk, V.P.; Kaune, M.; von Amsberg, G.; Dyshlovoy, S.A. Total Syntheses and Preliminary Biological Evaluation of Brominated Fascaplysin and Reticulatine Alkaloids and Their Analogues. Mar. Drugs 2019, 17, 496.

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