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2004
Oxazine derivatives
R 0595
Synthesis and Biological Evaluation of Benzo[7,8]chromeno[5,6-b][1,4]ox— The benzoxazine, khellactone, and (lapachone)benzene moieties are
52- 140 azin-3-ones.
combined to prepare the title compounds as possible antiinflammatory and antioxidant
agents. Treatment of O-methylmonoximes (III) of stenocarpoquinone-A (I) with methyl phenylacetate (IV) affords the oxazole (V) and oxazinone (VI). A reaction mechanism suggests the formation of (V) and (VI) via initially formed radicals. The release
of a water molecule in (VI) leads to the formation of the unsaturated compound (VII),
which is oxidized to hydroxy compounds (VIII) and (IX). Reaction of (VIII) with camphanic chloride (X) yields the monoester (XI) and two isomeric bisesters, (XII) and
(XIII). All compounds are strongly fluorescent. Compounds (V), (VII), and (XIII)
strongly inhibit soybean lipoxygenase. The reducing abilities of the compounds are
determined by their interaction with DPPH. Compounds (VIII) and (XII) compete significantly with dimethylsulfoxide for hydroxyl radicals. — (NICOLAIDES*, D. N.;
GAUTAM, D. R.; LITINAS, K. E.; HADJIPAVLOU-LITINA, D. J.;
KONTOGIORGIS, C. A.; J. Heterocycl. Chem. 41 (2004) 4, 605-611; Lab. Org.
Chem., Dep. Chem., Aristotle Univ. Thessaloniki, GR-54124 Thessaloniki, Greece;
Eng.) — H. Hoennerscheid
2004
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