936737-59-6Relevant academic research and scientific papers
Short syntheses of (+)-ferruginol from (+)-dehydroabietylamine
González, Miguel A.,Pérez-Guaita, David
, p. 9612 - 9615 (2012)
Short syntheses of bioactive (+)-ferruginol in five or six synthetic steps starting from commercially available (+)-dehydroabietylamine are described. The oxygenated function at C12 was introduced via a Friedel-Crafts acylation of N-phthaloyldehydroabietylamine followed by Baeyer-Villiger oxidation. Then, overall deprotection of functional groups, reductive deamination or biomimetic oxidative deamination, and final Wolff-Kishner reduction provided (+)-ferruginol in 21 and 23% overall yields, respectively.
Synthesis and properties of optically pure phenols derived from (+)-dehydroabietylamine
Malkowsky, Itamar M.,Nieger, Martin,Kataeva, Olga,Waldvogel, Siegfried R.
, p. 773 - 778 (2007)
Enantiomerically pure phenols are readily available in a straightforward sequence starting from (+)-dehydroabietylamine. Detailed synthetic protocols, analytical data and conversion to a monodentate phosphite ligand are presented. Georg Thieme Verlag Stuttgart.
Syntheses of C-ring modified dehydroabietylamides and their cytotoxic activity
Wiemann, Jana,Fischer, Lucie,Rohmer, Matthias,Csuk, René
, p. 861 - 870 (2018/07/31)
Due to their auspicious pharmacological efficacy as future drug candidates, natural products have been attracting scientific interest for centuries. An interesting field of research concerns the natural product class of terpenes. In this regard, a multitude of studies have already shown their promising biological potential. Therefore, a set of 27 derivatives of the diterpene dehydroabietylamine was synthesized, focusing on C-ring modifications and the derivatization of the amino moiety at C-18. Subsequent screening of the compounds in colorimetric sulforhodamine B-assays revealed an in vitro cytotoxicity especially towards malignant cell line MCF7. Particularly, 12-hydroxy-N-(isonicotinoyl)dehydroabietylamine and N-(4-methoxybenzoyl)dehydroabietylamine showed good cytotoxic activities (EC50 (MCF7) = 4.3 ± 0.2 μM and EC50 (MCF7) = 4.5 ± 1.5 μM, respectively) and significant selectivities (SI = 6.2 and SI = 8.8, respectively) towards malignant cell lines.
