After more than 70 years since its discovery, CF3CHN2 was found to possess a novel reactivity mode: N-terminal electrophile. With C-nucleophiles it gives hydrazones that are easily transformed into valuable CF3-heterocycles.
Reaction of Boc-protected amino acids with 3-phenoxy-2-trifluoromethylchromones gave new, previously unknown aminoacyl derivatives.One of the most important problems of modem organic chemistry is the search for highly effective bioregulators having a broad spectrum of biological action at comparatively low toxicity. Modification of the structure of flavones by obtaining conjugates with amino acids is one of the routes for constructing new classes of biologically active substances, the properties of which are caused by the presence of several pharmacophore centers. A.s a result of biological screening among known aminoacyl derivatives of isoflavone, preparations have been found with high hypolipidemic and analeptic [3,4] The starting materials for the synthesis of 3-aryloxy-2-trifluoromethyl chromones were o~-phenoxy-2,4-dihydroxyacetophenones Ia-b, obtained by the condensation of the corresponding aryloxyacetonitriles with 4-ethylresorcinol under the conditions of the Hoesch-Houben reaction in a mixture of ether and benzene in the presence of zinc chloride. Ketones Ia, b were high melting colorless crystalline substances, readily soluble in acetone, chloroform, and alcohols, and gave an intense red-brown coloration with an alcoholic solution of ferric chloride caused by the formation of an intramolecular complex. In the 1H NMR spectra of ketones Ia,
The search for new highly effective drugs among the modified isoflavonoids is extremely promising. The broad spectrum of chemical and therapeutic activity with low toxicity in a series of natural isoflavones, coupled with an adequate degree of study of the products of their metabolism, creates real prospects for the comprehensive application of the substances in medical practice. Synthetic products are becoming more and more interesting in addition to the products isolated from natural raw material [2]. Of undoubted interest among the synthetic products are the 3-phenoxyl derivatives of chromone, which exhibit cholagogue [3]
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.