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2005
Other bioactive products
U 1300
Umbelliferone Aminoalkyl Derivatives, a New Class of Squalene-Hopene Cyclase
— O-Alkylation of umbelliferone is achieved by treatment with alkyl bro11- 242 Inhibitors.
mides and base or by the Mitsunobu reaction under sonochemical conditions. Amino
functions are inserted into the side chain of the umbelliferone nucleus by i) microwave-promoted Mannich aminomethylation of the terminal alkyne in (I), ii) reductive
amination under high-intensity ultrasound conditions, cf. (V)→(VII), and iii) classic
nucleophilic substitution with alkyl bromides. The majority of derivatives is uniformly
active as inhibitors of squalene-hopene cyclase from A. acidocaldarius. The activity of
(IVb) approaches that of the anticholesteremic drug Ro 48-8071. — (CRAVOTTO*,
G.; BALLIANO, G.; TAGLIAPIETRA, S.; PALMISANO, G.; PENONI, A.; Eur. J.
Med. Chem. 39 (2004) 11, 917-924; Dip. Sci. Tecnol. Farm, Univ. Torino,
I-10125 Torino, Italy; Eng.) — H. Hoennerscheid
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