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Synthetic secofriedelane and friedelane derivatives as inhibitors of human lymphocyte proliferation and growth of human cancer cell lines in vitro

Title
Synthetic secofriedelane and friedelane derivatives as inhibitors of human lymphocyte proliferation and growth of human cancer cell lines in vitro
Type
Article in International Scientific Journal
Year
2001
Authors
Moiteiro, C
(Author)
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Justino, F
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Tavares, R
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Marcelo Curto, MJ
(Author)
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Florencio, MH
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Pedro, M
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Cerqueira, F
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Pinto, MMM
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Journal
Vol. 64
Pages: 1273-1277
ISSN: 0163-3864
Scientific classification
FOS: Medical and Health sciences > Basic medicine
Other information
Authenticus ID: P-000-T5W
Abstract (EN): Controlled silylation of friedelin (1) from cork smoker wash solids, a byproduct generated during processing of corkboard by steam baking, gave 3-trimethylsiloxyfriedel-2-ene (3) in high yields. Oxidation of 3 with OsO4/NMMO produced 2 alpha -hydroxyfriedelan-3-one (cerin) (5), from which the new 2,3-secofriedelan-2-al-3-oic acid (6) was obtained quantitatively by periodic acid oxidation. Oxidation of 3 with DDQ afforded friedel-1-en-3-one (8). Reductive ozonolysis of 3 gave 2 alpha ,3 beta -dihydroxyfriedelane, pachysandiol A (7). Compound 6 proved to be a potent inhibitor of human lymphocyte proliferation (IC50 = 10.7 muM) and of the growth of a human cancer cell line (GI(50) = 5.4-17.2 muM). C-13 NMR data for compounds (3, 4, 5, 6a, 7, and 8) are described for the first time.
Language: English
Type (Professor's evaluation): Scientific
Contact: cristina.moiteiro@mail.ineti.pt; regina.tavares@mail.ineti.pt
No. of pages: 5
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