The photostability
and antiproliferative activity of combretastatin
A-4 (CA-4) analogues against human epidermoid carcinoma cells A-431
were studied. For the first time, it was shown that UV or sunlight
irradiation of furanone analogues of CA-4 results in a photorearrangement
giving products with relatively low antiproliferative activity. The
observed ability of this series CA-4 to the photodegradation can be
used for the design of a new class of drug candidates with high selectivity
to cancer cells.
The acid-catalyzed cyclization of a wide range of triaryl-substituted divinyl ketones has been studied. It was found that the reaction pathway strongly depends on the nature of the aryl substituent at the α-position to the carbonyl group. An electron-rich aromatic substituent promotes the reaction to proceed through the intramolecular Friedel-Crafts electrophilic substitution giving dihydronaphthalene derivatives. In contrast, the presence of an electron-deficient substituent is favorable for the Nazarov 4π-conrotatory cyclization yielding triaryl-substituted cyclopentenones. The electrophilic substitution reaction was applied to thiophene and thiazole derivatives.
A novel quinazoline series of photoswitchable combretastatin A-4 (CA-4) analogues were synthesized and their photochemical properties and antiproliferative activity against A431 epidermoid carcinoma cells were studied. It was found that...
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