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

1
Department of Organic Chemistry and Laboratory of Biologically Active Compounds, School of Natural Sciences, Far Eastern Federal University, 8 Sukhanov Str., Vladivostok 690950, Russia
2
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, 159 Prospekt 100 Let Vladivostoku, Vladivostok 690022, Russia
3
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
4
Department of Oncology, Hematology and Bone Marrow Transplantation with Section Pneumology, Hubertus Wald-Tumorzentrum, University Medical Center Hamburg-Eppendorf, 20246 Hamburg, Germany
5
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; https://doi.org/10.3390/md17090496
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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