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2004
Terpenes
U 0200
46- 177
Synthesis and Antiangiogenic Activity of exo-Olefinated Deoxoartemisinin Derivatives. — Reaction of dihydroartemisinin (I) with thiols (II) yields a separable mixture
of major thioacetal dihydroartemisinins (III) with C-10α stereochemistry and minor
C-10β diastereomers (IV). The diastereomers (III) and (IV) are oxidized to the corresponding sulfonyl dihydroartemisinins. The C-10α-substituted compounds (V) are
subjected to a modified Ramberg—Baecklund rearrangement reaction to transform (V)
into the exo-olefinated deoxoartemisinin derivatives (VI), (VII), (VIII) and (IX). The
rearrangement proceeds stereoselectively affording a separable mixture of E- and
Z-isomers. Unlike sulfonyl reactants (Va) and (Vb), (Vc) bearing an aromatic sulfonyl
group, produces the benzylidene deoxoartemisinins (VIII) and (IX) with no bromide.
The title derivatives show strong inhibitory activity upon HUVEC growth with exception of mildly active Z-isomer (VIIa). E-isomer (VIa) shows good inhibition activity
against tube formation whereas (VIIa) and (VIb) are mildly effective. — (OH, S.;
JEONG, I. H.; SHIN, W.-S.; LEE*, S.; Bioorg. Med. Chem. Lett. 14 (2004) 14,
3683-3686; Dep. Basic Sci., Kwandong Univ. Coll. Med., Gangneung 210-701,
S. Korea; Eng.) — H. Hoennerscheid
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