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2004
Carbonyl derivatives
Q 0930
Cytotoxic—Antineoplastic Activity of Acetyl Derivatives of Prenylnaphthohydro— Hydroquinone derivatives related to diacetate (V) are synthesized to ana46- 097 quinone.
lyze the effect of substitution on the hydroquinonic part of the molecule on the bioactivity. Starting diacetate (V) is prepared from (III), which is obtained by "in situ" oxidation of dihydroxyacetophenone (I) to acetylbenzoquinone, followed by Diels—Alder
reaction with α-myrcene (II). Heating of (III) in xylene induces acyl migration and subsequent acetylation of the rearranged benzoquinone affords diacetate (V). The terpenic
part of (V) is modified taking into account previous results, particularly those contributing to the enhancement of cytotoxicity. The 3'-acetyl derivatives are evaluated for
their cytoxicity against cultured cells of A-549 human lung carcinoma and H-116
human colon carcinoma. Only derivative (X) displays inhibitory activity in the same
range as that observed for related potent derivatives against A-549. — (MOLINARI*,
A.; OLIVA, A.; MIGUEL DEL CORRAL, J. M.; CASTRO, M. A.; ARAYA, C.;
GARCIA-GRAVALOS, M. D.; SAN FELICIANO, A.; Farmaco 59 (2004) 8,
651-656; Inst. Quim., Univ. Catol. Valparaiso, Valparaiso 4059, Chile; Eng.) —
H. Hoennerscheid
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