End-group differentiating ozonolysis of furocoumarins

Malakhov, Mikhail V.; Dubinnyi, Maxim A.; Vlasova, N. V.; Zgoda, Victor G.; Efremov, Roman G.; Болдырев, Иван

doi:10.1039/c4ra08106d

Cited by 3 publications

(2 citation statements)

References 28 publications

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“…Unfortunately, this approach was found to not be applicable for unsubstituted Umb o-formylation, in the course of which the formation of yellow-red resin was observed. This process was visually similar to that observed earlier for the psoralen ozonolysis procedure also aimed at the preparation of 6-FUmb [26], and it was presumed that both microwave treatment and ozonolysis might lead to a polymerization of starting material (Umb) and/or its formylated products.…”

Section: Optimization Of the Duff Reaction Conditionssupporting

confidence: 82%

Twice as Nice: The Duff Formylation of Umbelliferone Revised

et al. 2021

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More efficient and preferably more convenient and greener synthetic solutions in coumarin scaffold functionalization are in steady demand. The Duff ortho-formylation of unsubstituted umbelliferone was revised in this study. The reaction conditions were optimized based upon data from the literature analysis and resulted in unexpectedly rapid ortho-formylation of umbelliferone, yielding a mixture of ortho-formyl position isomers. Thorough studies on the separation of ortho-formylated umbelliferones using chromatographic and recrystallization methods as well as the evaluation of their solubility in common organic solvents led to complete resolution of 8-formyl- and 6-formylumbelliferones. The precise protocol for simultaneous preparation, extraction, and purification of 8-formyl- and 6-formylumbelliferones is provided, and the prospective studies of biological and pharmacological activities of these compounds are synopsized.

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Section: Optimization Of the Duff Reaction Conditionssupporting

confidence: 82%

Twice as Nice: The Duff Formylation of Umbelliferone Revised

et al. 2021

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“…High reactivity of these photoproducts towards both biological targets and one another provides a wide field to interpret the results. In further studies, attention will be particularly focused on the mechanisms of formation and activity of aldehydic photoproducts, since their methods of prepara tion are known from the literature [15,43]. Furthermore, the mechanisms of formation and chemical structure of peroxidic photoproducts are of interest, since the pro moting role of peroxides in aldehyde induced hemolysis is also known [44].…”

Section: Chemical Regulation Of Pop Hemolysismentioning

confidence: 98%

On the mechanism of erythrocyte hemolysis induced by photooxidized psoralen

Nevezhin

Vlasova

Pyatnitskiy

et al. 2015

Biochemistry Moscow

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Contemporary concepts on a possible mechanism of erythrocyte hemolysis induced by photooxidized psoralen - the medicinal photosensitizing furocoumarin - are reviewed. The hypothesis on the mechanochemical mechanism of hemolysis is considered in view of recent data on photoinduced aggregation in photooxidized psoralen solutions. Appropriate chemical structures of photoproduct hemolysins and aggregating photoproducts are discussed.

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