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Mar. Drugs 2018, 16(12), 481; https://doi.org/10.3390/md16120481

Synthesis and Antiproliferative Activity of Marine Bromotyrosine Purpurealidin I and Its Derivatives

1
Drug Research Program, Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, Viikinkaari 5 E (P.O. Box 56), University of Helsinki, FI-00014 Helsinki, Finland
2
Drug Research Program, Division of Pharmaceutical Biosciences, Faculty of Pharmacy, Viikinkaari 5 E (P.O. Box 56), University of Helsinki, FI-00014 Helsinki, Finland
3
Institute of Chemistry, Technische Universität Chemnitz, 09107 Chemnitz, Germany
Current address: Government First Grade College, Chamarajanagar 571313 (Affiliated to University of Mysore), India.
*
Author to whom correspondence should be addressed.
Received: 6 November 2018 / Revised: 20 November 2018 / Accepted: 27 November 2018 / Published: 3 December 2018
(This article belongs to the Special Issue Marine Bioactive Natural Product Studies in Europe)
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Abstract

The first total synthesis of the marine bromotyrosine purpurealidin I (1) using trifluoroacetoxy protection group and its dimethylated analog (29) is reported along with 16 simplified bromotyrosine derivatives lacking the tyramine moiety. Their cytotoxicity was evaluated against the human malignant melanoma cell line (A-375) and normal skin fibroblast cells (Hs27) together with 33 purpurealidin-inspired simplified amides, and the structure–activity relationships were investigated. The synthesized simplified analogs without the tyramine part retained the cytotoxic activity. Purpurealidin I (1) showed no selectivity but its simplified pyridin-2-yl derivative (36) had the best improvement in selectivity (Selectivity index 4.1). This shows that the marine bromotyrosines are promising scaffolds for developing cytotoxic agents and the full understanding of the elements of their SAR and improving the selectivity requires further optimization of simplified bromotyrosine derivatives. View Full-Text
Keywords: Purpurealidin I; bromotyrosines; Pseudoceratina purpurea; synthesis; cytotoxicity; selectivity to cancer cells Purpurealidin I; bromotyrosines; Pseudoceratina purpurea; synthesis; cytotoxicity; selectivity to cancer cells
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Bhat, C.; Ilina, P.; Tilli, I.; Voráčová, M.; Bruun, T.; Barba, V.; Hribernik, N.; Lillsunde, K.-E.; Mäki-Lohiluoma, E.; Rüffer, T.; Lang, H.; Yli-Kauhaluoma, J.; Kiuru, P.; Tammela, P. Synthesis and Antiproliferative Activity of Marine Bromotyrosine Purpurealidin I and Its Derivatives. Mar. Drugs 2018, 16, 481.

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