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Persulfate-mediated decarboxylation of arylacetic acids is well-versed and a preferred choice for functionalization. However, certain substituted arylacetic acids do not follow the expected decarboxylation trend and may lead to other different functionalizations, which remain elusive in the literature. The effect of ortho-substitution on persulfate-mediated decarboxylation and functionalization of arylacetic acids forms the basis of this report, wherein the presence of different electron-withdrawing or electron-releasing groups exerts different effects on the fate as well as rate of decarboxylation. In so doing, the synthesis of ortho-hydroxy N-arylacetamides under persulfate-mediated one-pot conditions is developed. [ABSTRACT FROM AUTHOR]

An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance. [ABSTRACT FROM AUTHOR]

Abstract Background Human influenza viruses are known to bind to sialic acid linked α2-6 to galactose, but the binding specificity beyond that linkage has not been systematically examined. H3N2 human influenza isolates lost binding to chicken red cells in the 1990s but viruses isolated since 2003 have re-acquired the ability to agglutinate chicken erythrocytes. We have investigated specificity of binding, changes in hemagglutinin sequence of the recent viruses and the role of sialic acid in productive infection. Results Viruses that agglutinate, or do not agglutinate, chicken red cells show identical binding to a Glycan Array of 264 oligosaccharides, binding exclusively to a subset of α2-6-sialylsaccharides. We identified an amino acid change in hemagglutinin that seemed to correlate with chicken red cell binding but when tested by mutagenesis there was no effect. Recombinant hemagglutinins expressed on Sf-9 cells bound chicken red cells but the released recombinant baculoviruses agglutinated only human red cells. Similarly, an isolate that does not agglutinate chicken red cells show hemadsorption of chicken red cells to infected MDCK cells. We suggest that binding of chicken red cells to cell surface hemagglutinin but not to virions is due to a more favorable hemagglutinin density on the cell surface. We investigated whether a virus specific for α2-6 sialyloligosaccharides shows differential entry into cells that have varying proportions of α2-6 and α2-3 sialic acids, including human A549 and HeLa cells with high levels of α2-6 sialic acid, and CHO cells that have only α2-3 sialic acid. We found that the virus enters all cell types tested and synthesizes viral nucleoprotein, localized in the nucleus, and hemagglutinin, transported to the cell surface, but infectious progeny viruses were released only from MDCK cells. Conclusion Agglutination of chicken red cells does not correlate with altered binding to any oligosaccharide on the Glycan Array, and may result from increased avidity due to density of hemagglutinin and not increased affinity. Absence of α2-6 sialic acid does not protect a cell from influenza infection and the presence of high levels of α2-6-sialic acids on a cell surface does not guarantee productive replication of a virus with α2-6 receptor specificity.

Diarylmethanes are cardinal scaffolds by virtue of their unique structural feature including the presence of a benzylic CH2 group that can be easily functionalized to generate a variety of fascinating molecules holding immense importance in pharmaceutical, agrochemical, and material sciences. While the originally developed protocols for benzylic C−H functionalization in diarylmethanes employing base‐mediated and metal‐catalyzed strategies are still actively used, they are joined by a new array of metal‐free conditions, offering milder and benign conditions. With the recent surge of interest towards the synthesis of functionalized diarylmethanes, numerous choices are now available for a synthetic organic chemist to transform the benzylic C−H bond to C−C or C−X bond offering the synthesis of any molecule of choice. This review highlights benzylic methylene (CH2) functionalizations of diaryl/heteroarylmethanes utilizing various base‐mediated, transition‐metal‐catalyzed, and transition‐metal free approaches for the synthesis of structurally diverse important organic molecules, often with a high chemo‐, regio‐ and enantio‐selectivity. This review also attempts to provide analysis of the scope and limitations, mechanistic understanding, and sustainability of the transformations. [ABSTRACT FROM AUTHOR]